Category Archives: Dangerous chemicals

Post 150: Choice Chronicles of the Chronicle Flask

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From citric to hydrofluoric, acids are an ever-popular topic

I began this blog in 2013, and since then I’ve written at least one post a month. This will be the 150th.

I put love and care into all my posts and, in turn, this blog has been good to me. Although no one’s ever paid me to write it, it has brought me work over the years – many people have asked me to write for them having read things here. But life is busier now than it’s ever been, and it’s time to wind things down. You’ll continue to find my non-fiction here and there, I’ll still be regularly updating my fiction blog, and if you want the latest info, look me up on Twitter. In particular, check out the #272sci hashtag for tiny bits of bite-sized science.

In the meantime, how about a little reminder of some of this blog’s most popular, most important, or just my favourite, posts? Let’s go!

The acid that really does eat through everything (2013)
Turns out, everyone loves acid – this post is one of my all-time most viewed. I guess there’s just something compelling about substances that can dissolve metal, and this one is particular special (and terrifying) for its ability to also dissolve glass and ceramic. (Oh, and sorry about the double spaces after the full stops. It was a long time ago. I know better now.)

Butyric acid, a very smelly molecule (2014)
On the subject of acids, this has been another popular post. I suppose if there’s anything more fun than an acid that eats through the bottle you’re trying to store it in, it’s an acid that smells of Parmesan and vomit. Seriously, it is an interesting one: we’re all familiar with the smell of ethanoic acid (aka acetic acid, found in vinegar), and propanoic acid (propionic acid) merely smells a bit sweaty, but add one more carbon and, hoo boy, you have an utterly revolting stench that some people are so sensitive to they can still detect it weeks, even months, after cleaning.

It’s important to understand what sugar actually is if you want to reduce your intake

Sugar that’s not sugar? (2015)
People talk a lot of nonsense about sugar. A particular pet hate of mine is people calling products sugar-free when they’re nothing of the sort, or implying that the type of sugary ingredient they’ve put in the thing they’re trying to sell you is somehow extra-healthy. If actually reducing your sugar intake is your goal (and it’s not a terrible one), this piece might help.

MMS and CD chemistry – the facts (2016)
This is my simple explainer about MMS (‘miracle’ or ‘master’ mineral solution) and CD (chlorine dioxide). This horrible, nasty fad seems to have faded away in recent years – partly thanks to the fact that even its founder, Jim Humble, admitted it cures nothing – but then again, I have seen CD-MMS linked to pseudoscientific Covid ‘cures’. Let’s hope this post continues to do its job as a useful reference for anyone that needs it.

Absurd alkaline ideas – history, horror and jail time (2017)
Continuing the theme of health, I’ve written several posts about so-called ‘alkaline’ diets, and this isn’t the most popular (that would be Amazing Alkaline Lemons?) but this is the one I wish more people would read. It explains where the whole silly notion came from in the first place. (As does this Twitter thread, slightly more succinctly.)

There really is no need to panic about slime

No need for slime panic: it’s not going to poison anyone (2018)
I’ve yet to meet a child who doesn’t love slime, and every now and then the gooey stuff becomes so popular that we start to see scare stories. So it was in 2018. However, with a few sensible precautions, slime really isn’t dangerous. It’s all explained here.

Let’s speed up the rate at which we recognise our female chemists (2019)
This one was all about the little-known Elizabeth Fulhame. She was the first chemist to describe catalytic reactions – in 1794, when the more famous Berzelius was a mere teenager. Let’s remember her name.

Chemical connections: dexamethasone, hydroxychloroquine and rheumatoid arthritis (2020)
Covid hit us in 2020, and it would prompt more than one post – including this one when dexamethasone had its moment in the spotlight. Probably an unfamiliar drug to most people before this point, dexamethasone was one of the first practical treatments for rheumatoid arthritis in the mid-20th century. Unlike some other much-hyped treatments, we have solid evidence for the effectiveness of this medicine – although it is really only useful for people suffering with very severe symptoms. Still, it’s pretty cool that an old drug turned out to be such a useful tool in a modern pandemic.

There’s chemistry in your skin

Sunshine, skin chemistry, and vitamin D (2020)
To make it a nice, round ten, I’ll sneak in another 2020 post. This one is all about vitamin D. A lot of people are very critical of supplements, and while I understand their position, this particular case is slightly different. If you live in certain parts of the world, you really, really should be considering vitamin D supplementation for at least part of the year, and this post will tell you why.

Brilliant Bee Chemistry! (2021)
This one wasn’t so long ago, but I love it. Bees are fascinating creatures, and if you don’t know what the connection between bees and bananas is, you ought to have a read.

So, this is it, folks – thank you, it’s been fun! Happy New Year!

Content is © Kat Day 2022. You may share or link to anything here, but you must reference this site if you do. You can still support my writing my buying a super-handy Pocket Chemist from Genius Lab Gear using the code FLASK15 at checkout (you’ll get a discount, too!) or by buying me a coffee – just hit this button:
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Neem: nice, nasty or… not sure?

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A few days ago it was sunny and slightly breezy outside (yes, it’s August, but I live in the UK – this isn’t as common as you might imagine) and I thought, I should make the most of this and do something about my orchids.

Now, anyone that reads this blog regularly will know that my Dad is a horticulturist. I, however, am not. My fascination with bright colours, interesting smells and complicated naming conventions went down the chemistry route. But I am, oddly, quite good with Phalaenopsis, aka, moth orchids. I don’t really know why, or how, but I seem to have come to some sort of agreement with the ones that live on my kitchen windowsill. It goes along the lines of: I’ll water you once a week, and you make flowers a couple of times a year, and we’ll otherwise leave each other alone, okay?

Scale bugs secrete honeydew, which encourages the growth of sooty moulds

Well, this was fine for years, until we somehow acquired an infestation of scale bugs. These tiny but extremely annoying pests feed by sucking sap from leaves of plants, and they excrete a sticky substance called honeydew. Trust me, it’s not as nice as it sounds. Firstly, it really is sticky, and makes a horrible mess not just of the orchid leaves, but also the area around the plants.

Then it turns out that certain types of mould just love this stuff, so you end up with black spots on the leaves. And, not surprisingly, all this weakens the plant.

So, what’s the answer? Well, there are several. But the one I tend to default to is neem oil.

This stuff is a vegetable oil from the seeds of the Azadirachta indica, or neem, tree. It has a musty, nutty sort of smell, and is fairly easy to buy.

It’s indigenous to the Indian subcontinent and has been historically important in traditional medicine. In fact, The Sanskrit name of this evergreen tree is ‘Arishtha’, which means ‘reliever of sickness’.

So it’s a natural vegetable oil and people have been using it as a remedy for thousands of years – must be totally safe, right? Right?

Well… I’ve said it before, but some of the very best horribly toxic things are entirely natural, and neem is yet another example. Ingestion of significant quantities can cause metabolic acidosis (finally, something that really does have the potential to change blood pH! Er… but not… in a good way), kidney failure, seizures, and brain damage in children. Skin contact can cause contact dermatitis. It’s been shown to work as a contraceptive and, more problematically, it’s a known abortifacient (causes miscarriage).

Neem oil is easy to buy, but it needs to be handled with caution

All this said, as always, the dose make the poison.

One case study in the Journal of The Association of Physicians of India reported on a 36-year-old man who swallowed 30–50 ml (about three tablespoons) of neem oil, in the hope of treating the corns on his feet. As far as I can tell, it didn’t help his corns. It did cause vomiting, drowsiness, a dangerous drop in blood pH and seizures. There’s no specific antidote for neem poisoning, but the hospital managed his symptoms. Luckily, despite the hammering his kidneys undoubtedly took, he didn’t need dialysis, and was discharged from hospital after just over a week.

Now, okay, you’re unlikely to accidentally swallow three tablespoons of any oil, especially not neem which does have quite a strong, not entirely pleasant, smell and (reportedly – I haven’t tried for obvious reasons) a bitter taste. But nevertheless, it’s wise to be cautious, particularly around children who have a smaller body mass and therefore are much more likely to suffer serious effects – up to and including death. In one reported case, a mother gave a 3-month-old child a teaspoon of neem oil in the hope of curing his indigestion – fortunately he survived, but not without some seriously scary symptoms.

Nimbin, a chemical found in neem oil, is reported to have all sorts of beneficial effects [image source]

Okay, so those are the dangers. Let’s talk chemistry. The Pakistani organic chemist Salimuzzaman Siddiqui is thought to be the first scientist to formally investigate the various compounds in neem oil. In 1942 he extracted three compounds, and identified nimbidin as the main antibacterial substance in neem. He was awarded an OBE in 1946 for his discoveries.

I will confess, at this point, to running into a little bit of confusion with the nomenclature. Nimbidin is described, in some places at least, as a mixture of compounds (collectively, tetranortriterpenes) rather than a single molecule. But either way, it has been shown to have anti-inflammatory properties – at least in rats.

Another of the probably-mostly-good substances in neem is nimbin: a triterpenoid which is reported to have a whole range of positive properties, including acting as an anti-inflammatory, an antipyretic, a fungicide, an antiseptic and even as an antihistamine. Interestingly, I went looking for safety data on nimbin, and I couldn’t find much. That could mean it’s safe, or it could mean it just hasn’t been extensively tested.

Azadirachtin, another chemical found in neem, is a known pesticide [image source]

The substance that seems to do most of the pesticide heavy lifting is azadirachtin. This is a limonoid (compounds that are probably best known for their presence in citrus fruits). It’s what’s called an antifeedant – a substance produced by plants to deter predators from munching on them. Well, mostly. Humans have a strange habit of developing a taste for plants that produce such substances. Take, for example, odoriferous garlic, clears-out-your-sinuses horseradish, and of course the daddy of them all: nicotine.

Azadirachtin is known to affect lots of species of insects, both by acting as an antifeedant and as a growth disruptor. Handily, it’s also biodegradable – and breaks down in a few days when exposed to light and water.

That makes it appealing as a potential pesticide, and it’s also generally described as having low toxicity in mammals – its reported LD50 tends to fall into the grams per kilogram range, which makes it “moderately to slightly toxic“. Wikipedia quotes a value (without a source, as I write this) of >3,540 mg/kg in rats.

But… I did find another page quoting 13 mg/kg in mice. That’s quite dramatically different, and would make it extremely/highly toxic. Unfortunately I couldn’t get my hands on the original source, so I haven’t been able to verify it’s not a transposition error.

Let’s assume it isn’t. It would be odd to have such a big difference between mice and rats. Things that poison mice tend to poison rats, too. There might be some confusion over pure azadirachtin vs. “neem extract” – it could be the case that the mixture of chemicals working together in neem create some sort of synergistic (toxic) effect – greater than the sum of all the individual substances. It could be an experimental error, including a contaminated neem sample, or something to do with the way the animals were exposed to the extract.

Neem soap is widely available online, but that may not be a good thing…

It’s difficult to say. Well, it’s difficult for me to say, because I don’t have access to all the primary sources. (Any toxicologists out there, please do feel free to weigh into the comments section!) But either way, as I’ve already mentioned, several case studies have fingered azadirachtin as one of the substances likely to be causing the well-reported nasty side effects.

If you’re asking this chemist? I say be careful with the stuff. If you decide to use it on your plants, keep it out of reach of children, and wear some good-quality disposable gloves while you’re handling it (I put some on after I took that photo back there). If you’re pregnant, or trying to become pregnant, the safest option is to not use it at all.

Which brings me to neem soap.

Yup. It’s sold as a “natural” treatment for skin conditions like acne. I won’t link to a specific brand, but it’s easy to find multiple retailers with a simple Google search. I looked at one selling soap bars for £6.99 a pop, containing 10% (certified organic, because of course) neem oil. Did I mention back there that neem is known to cause contact dermatitis? I’m fairly sure I did. None of the products I saw had obvious safety warnings, and I certainly found nothing about safety (or otherwise) for pregnant women.

Plus – worryingly, not least because children are more likely to get things in their mouth – you can also buy kids and babies versions, again purporting to contain 10% neem oil.

I even found neem toothpaste. Which… given people often swallow toothpaste… yikes.

My moth orchids are looking much healthier now I’ve got rid of all the scale bugs!

Now again, and for the umpteenth time, the dose makes the poison. The case studies I’ve mentioned involved, at a minimum, swallowing a teaspoon of pure neem oil, and you’re not getting that sort of quantity from smears of toothpaste. But, at the same time, when it comes to pregnancy and babies, it’s generally sensible to apply a precautionary principle, especially for things like soap and toothpaste for which alternatives with well-established safety profiles exist.

Bottom line? Would I use these products? I would not.

But I do use neem to treat the scale bugs on my orchids, and they’re doing much better than they were. Fingers crossed for more flowers!

Do you want something non-sciency to distract you from, well, everything? Why not take a look at my fiction blog: the fiction phial? You can also find me doing various flavours of editor-type-stuff at the horror podcast, PseudoPod.org – so head over there, too!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2021. You may share or link to anything here, but you must reference this site if you do. You can support my writing my buying a super-handy Pocket Chemist from Genius Lab Gear using the code FLASK15 at checkout (you’ll get a discount, too!) or by buying me a coffee – the button is right here…
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Onerous ovens: why is cleaning the cooker such a chore?

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As I write Thanksgiving was a few days ago, when most Americans traditionally cook a very large meal based around roasted turkey. Most Brits – and other countries of course – have the same thing coming up soon in the form of Christmas, and there are lots of other celebrations around this time of year that seem to feature cooking and food quite heavily.

Whatever your traditions, then, it’s a time when many of us frown critically at the dark, sticky depths of our oven and wonder if, perhaps, we should attempt to give it a clean. Or at least pay someone else to come and clean it.

Why is oven cleaning such a difficult and unpleasant job, anyway? It’s not that hard to clean other surfaces, is it? Why are ovens so particularly awful?

Well, to explain this, we first need to understand fats.

Fats vaporise during cooking.

Most of the grime in your oven is fat, combined with the carbonised remains of… something or other. The sorts of fats that are common in animal and plant products have boiling points around the 300 oC mark (animal fats typically having higher values than plant oils), but they start to form vapours at much lower temperatures, and certainly at typical cooking temperatures there’s plenty vaporised oil around. Besides, under typical conditions most oils will “smoke” – i.e. start to burn – long before they get close to boiling.

We’re all familiar with the idea that fats don’t mix well with water, and herein lies the problem: all that fatty gloop that’s stuck to the inside of your oven just doesn’t want to come off with standard cleaning methods, particularly when it’s built up over time.

Can chemistry help us here? What are fats, chemically? Well, they’re esters. Which may or may not mean anything to you, depending on how much chemistry you can remember from school. But even if you don’t remember the name, trust me, you know the smell. In particular, nail polishes and nail polish removers contain the simple ester known as ethyl acetate, otherwise known as ethyl ethanoate. (Some people say this chemical smells like pear drops which… only really helps if you know what pear drops smell like. Look, it smells of nail polish, okay?)

Fats are esters (image source)

Anyway, the point is that esters have a particular sequence of atoms that has a carbon bonded to an oxygen, which is bonded to another carbon, which is in turn double-bonded to oxygen. This is a bit of a mouthful, so chemists often write it as COOC. In the diagram here, oxygen atoms are red while carbon atoms are black.

There are actually three ester groups in fat molecules – which explains why fats are also known as triglycerides.

In terms of general chemistry, esters form when a carboxylic acid (a molecule which contains a COOH group) reacts with an alcohol (a molecule that contains an OH group). And this is where it all starts to come together – honest – because you’ve probably heard of fatty acids, right? If nothing else, the words turn up in certain food additive names, in particular E471 mono- and diglycerides of fatty acids, which is really common in lots of foods, from ice cream to bread rolls.

Glycerol is a polyol — a molecule that contains several alcohol groups (image source)

Well, this reaction is reversible, and as a result fats (which are esters, remember) break up into fatty acids and glycerol – which is a polyol, that is, a molecule with several alcohol groups. Or, to look at it the other way around: fats are made by combining fatty acids with glycerol.

And the reason it’s useful to understand all this is that the way you break up esters, and therefore fat, is with alkalis. (Well, you can do it with acid, too, but let’s not worry about that for now.)

Strong alkalis break up fats in a chemical reaction called hydrolysis — the word comes from the Greek for water (hydro) and unbind (lysis) and so literally means “split up with water”. Humans have known about this particular bit of chemistry for a long time, because it’s fundamental to making soap. As I said a few months ago when I was banging on about hand-washing, the ancient Babylonians were making soap some 4800 years ago, by boiling fats with ashes – which works because alkaline compounds of calcium and potassium form when wood is burnt at high temperatures.

The grime in ovens is mostly fat.

The really clever thing about all this is that two things are happening when we mix alkali with fat: not only are we breaking up the fat molecules, but also the substances they break up into are water-soluble (whereas fats, as I said at the start, aren’t). Which makes them much easier to clean away with water. Obviously this is the very point of soap, but it’s also handy when trying to get all that baked-on gunk off your oven walls.

Now, in theory, this means you could get some lye (aka sodium hydroxide, probably), smear it all over your oven and voilà. But I don’t recommend it, for a few reasons. Firstly, it’s going to be difficult to apply, since sodium hydroxide is mostly sold as pellets or flakes (it’s pretty easy to buy, because people use it to make soap).

Sodium hydroxide, sometimes called lye, is often sold in the form of pellets.

But, you say, couldn’t I just dissolve it in water and spray or spread it on? Yes, yes you could. But it gets really, really hot when you mix it with water. So you need to be incredibly careful. Because, and this is my next point, chemically your skin is basically fat and protein, and this reaction we’re trying to do on oven sludge works equally well on your skin. Only, you know, more painfully, and with scarring and stuff. In short, if you’re handing lye, wear good nitrile on vinyl gloves and eye protection.

Actually, regardless of how you’re cleaning your oven you should wear gloves and eye protection, because the chemicals are still designed to break down fats and so… all of the above applies. It’s just that specially-designed oven cleaners tend to come with easier (and safer) ways to apply them. For example, they might come as a gel which you can paint on, and/or with bags that you can put the racks into, and may also be sold with gloves and arm protectors (but rarely goggles – get some separately). They might also have an extra surfactant, such as sodium laureth sulfate, added to help with breaking down grease. The main ingredient is still either potassium hydroxide or sodium hydroxide, though.

Well, possibly, but also not really, if you’re sensible.

As an aside, it makes me smile when I come across an article like this which talks about the “serious” chemicals in oven cleaners and more “natural” ways to clean your oven. The “natural” ways are invariably weak acids or alkalis such as lemon juice or baking soda, respectively. They’re essentially ineffective ways of trying to do exactly the same chemistry.

And okay, sure, the gel and the bag and so on in the modern kits are newer tech, but the strong alkali? Nothing more natural than that. As I said at the start, humans have literally been using it for thousands of years.

A point which really cannot be repeated enough: natural does not mean safe.

Fumes can be irritating to skin, eyes and lungs.

Speaking of which, you will get fumes during oven cleaning. Depending on the exact cleaning mixture involved, these will probably be an alkaline vapour, basically (haha) forming as everything gets hot. Such vapour is potentially irritating to skin, eyes and lungs, but not actually deadly toxic. Not that I recommend you stick your head in your freshly-scrubbed oven and inhale deeply, but you take my point. It might give food a soapy, possibly bitter (contrary to what’s stated in some text books, not all alkalis taste bitter, but do not experiment with this) taste if you really over-do it.

In short, if you’re cleaning your oven yourself: follow the manufacturer’s instructions, make sure your kitchen is well-ventilated, leave the oven door open for a while after you’ve finished and, to be really sure, give all the surfaces an extra wash down with plenty of water.

Put the cleaning off until January – after all, the oven’s only going to get dirty again.

And that’s… it, really. Whether you’re cleaning your own oven or getting someone else to do it for you, the chemistry involved is really, really old. And yes, the chemicals involved are hazardous, but not because they’re not “natural”. Quite the opposite.

Or you could just leave it. I mean, it’s only going to get dirty again when you cook Christmas dinner, right?

If you’re studying chemistry, have you got your Pocket Chemist yet? Why not grab one? It’s a hugely useful tool, and by buying one you’ll be supporting this site – it’s win-win! If you happen to know a chemist, it would make a brilliant stocking-filler! As would a set of chemistry word magnets!

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Want something non-sciency to distract you from, well, everything? Why not check out my fiction blog: the fiction phial.

Cleaning chemistry – the awesome power of soap

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Well, times are interesting at the moment, aren’t they? I’m not going to talk (much) about The Virus (there’s gonna be a movie, mark my words), because everyone else is, and I’m not an epidemiologist, virologist or an immunologist or, in fact, in any way remotely qualified. I am personally of the opinion that it’s not even especially helpful to talk about possibly-relevant drugs at the moment, given that we don’t know enough about possible negative interactions, and we don’t have reliable data about the older medicines being touted.

In short, I think it’s best I shut up and leave the medical side to the experts. But! I DO know about something relevant. What’s that, I hear you ask? Well, it’s… soap! But wait, before you start yawning, soap is amazing. It is fascinating. It both literally and figuratively links loads of bits of cool chemistry with loads of other bits of cool chemistry. Stay with me, and I’ll explain.

First up, some history (also not a historian, but that crowd is cool, they’ll forgive me) soap is old. Really, really, old. Archaeological evidence suggests ancient Babylonians were making soap around 4800 years ago – probably not for personal hygiene, but rather, mainly, to clean cooking pots. It was originally made from fats boiled with ashes, and the theory generally goes that the discovery was a happy accident: ashes left from cooking fires made it much easier to clean pots and, some experimenting later, we arrived at something we might cautiously recognise today as soap.

Soap was first used to clean pots.

The reason this works is that ashes are alkaline. In fact, the very word “alkali” is derived from the Arabic al qalīy, meaning calcined ashes. This is because plants, and especially wood, aren’t just made up of carbon and hydrogen. Potassium and calcium play important roles in tree and plant metabolism, and as a result both are found in moderately significant quantities in wood. When that wood is burnt at high temperatures, alkaline compounds of potassium and calcium form. If the temperature gets high enough, calcium oxide (lime) forms, which is even more alkaline.

You may, in fact, have heard the term potash. This usually refers to salts that contain potassium in a water-soluble form. Potash was first made by taking plant ashes and soaking them in water in a pot, hence, “pot ash”. And, guess where we get the word potassium from? Yep. The pure element, being very reactive, wasn’t discovered until 1870, thousands of years after people first discovered how useful its compounds could be. And, AND, why does the element potassium have the symbol K? It comes from kali, the root of the word alkali.

See what I mean about connections?

butyl ethanoate butyl ethanoate

Why is the fact that the ashes are alkaline relevant? Well, to answer that we need to think about fats. Chemically, fats are esters. Esters are chains of hydrogen and carbon that have, somewhere within them, a cheeky pair of oxygen atoms. Like this (oxygen atoms are shown red):

Now, this is a picture of butyl ethanoate (aka butyl acetate – smells of apples, by the way) and is a short-ish example of an ester. Fats generally contain much longer chains, and there are three of those chains, and the oxygen bit is stuck to a glycerol backbone.

Thus, the thick, oily, greasy stuff that you think of as fat is a triglyceride: an ester made up of three fatty acid molecules and glycerol (aka glycerine, yup, same stuff in baking). But it’s the ester bit we want to focus on for now, because esters react with alkalis (and acids, for that matter) in a process called hydrolysis.

Fats are esters. Three fatty acid chains are attached to a glycerol “backbone”.

The clue here is in the name – “hydro” suggesting water – because what happens is that the ester splits where those (red) oxygens are. On one side of that split, the COO group of atoms gains a metal ion (or a hydrogen, if the reaction was carried out under acidic conditions), while the other chunk of the molecule ends up with an OH on the end. We now have a carboxylate salt (or a carboxylic acid) and an alcohol. Effectively, we’ve split the molecule into two pieces and tidied up the ends with atoms from water.

Still with me? This is where it gets clever. Having mixed our fat with alkali and split our fat molecules up, we have two things: fatty acid salts (hydrocarbon chains with, e.g. COO– Na+ on the end) and glycerol. Glycerol is extremely useful stuff (and, funnily enough, antiviral) but we’ll put that aside for the moment, because it’s the other part that’s really interesting.

What we’ve done here is produce a molecule that has a polar end (the charged bit, e.g. COO– Na+) and a non-polar end (the long chain of Cs and Hs). Here’s the thing: polar substances tend to only mix with other polar substances, while non-polar substances only mix with other non-polar substances.

You may be thinking this is getting technical, but honestly, it’s not. I guarantee you’ve experienced this: think, for example, what happens if you make a salad dressing with oil and vinegar (which is mostly water). The non-polar oil floats on top of the polar water and the two won’t stay mixed. Even if you give them a really good shake, they separate out after a few minutes.

The dark blue oily layer in this makeup remover doesn’t mix with the watery colourless layer.

There are even toiletries based around this principle. This is an eye and lip makeup remover designed to remove water-resistant mascara and long-stay lipstick. It has an oily layer and a water-based layer. To use it, you give the container a good shake and use it immediately. The oil in the mixture removes any oil-based makeup, while the water part removes anything water-based. If you leave the bottle for a minute or two, it settles back into two layers.

But when we broke up our fat molecules, we formed a molecule which can combine with both types of substance. One end will mix with oily substances, and the other end mixes with water. Imagine it as a sort of bridge, joining two things that otherwise would never be connected (see, literal connections!)

There are a few different names for this type of molecule. When we’re talking about food, we usually use “emulsifier” – a term you’ll have seen on food ingredients lists. The best-known example is probably lecithin, which is found in egg yolks. Lecithin is the reason mayonnaise is the way it is – it allows oil and water to combine to give a nice, creamy product that stays mixed, even if it’s left on a shelf for months.

When we’re talking about soaps and detergents, we call these joiny-up molecules “surfactants“. You’re less likely to have seen that exact term on cosmetic ingredients lists, but you will (if you’ve looked) almost certainly have seen one of the most common examples, which is sodium laureth sulfate (or sodium lauryl sulfate), because it turns up everywhere: in liquid soap, bubble bath, shampoo and even toothpaste.

I won’t get into the chemical makeup of sodium laureth sulfate, as it’s a bit different. I’m going to stick to good old soap bars. A common surfactant molecule that you’ll find in those is sodium stearate, which is just like the examples I was talking about earlier: a long hydrocarbon chain with COO– Na+ stuck on the end. The hydrocarbon end, or “tail”, is hydrophobic (“water-hating”), and only mixes with oily substances. The COO– Na+ end, or “head”, is hydrophilic (“water loving”) and only mixes with watery substances.

Bars of soap contain sodium stearate.

This is perfect because dirt is usually oily, or is trapped in oil. Soap allows that oil to mix with the water you’re using to wash, so that both the oil, and anything else it might be harbouring, can be washed away.

Which brings us back to the wretched virus. Sars-CoV-2 has a lipid bilayer, that is, a membrane made of two layers of lipid (fatty) molecules. Virus particles stick to our skin and, because of that membrane, water alone does a really bad job of removing them. However, the water-hating tail ends of surfacant molecules are attracted to the virus’s outer fatty surface, while the water-loving head ends are attracted to the water that’s, say, falling out of your tap. Basically, soap causes the virus’s membrane to dissolve, and it falls apart and is destroyed. Victory is ours – hurrah!

Hand sanitisers also destroy viruses. Check out this excellent Compound Interest graphic (click the image for more).

Who knew a nearly-5000 year-old weapon would be effective against such a modern scourge? (Well, yes, virologists, obviously.) The more modern alcohol hand gels do much the same thing, but not quite as effectively – if you have access to soap and water, use them!

Of course, all this only works if you wash your hands thoroughly. I highly recommend watching this video, which uses black ink to demonstrate what needs to happen with the soap. I thought I was washing my hands properly until I watched it, and now I’m actually washing my hands properly.

You may be thinking at this point (if you’ve made it this far), “hang on, if the ancient Babylonians were making soap nearly 5000 years ago, it must be quite easy to make… ooh, could I make soap?!” And yes, yes it is and yes you can. Believe me, if the apocolypse comes I shall be doing just that. People rarely think about soap in disaster movies, which is a problem, because without a bit of basic hygine it won’t be long before the hero is either puking his guts up or dying from a minor wound infection.

Here’s the thing though, it’s potentially dangerous to make soap, because most of the recipes you’ll find (I won’t link to any, but a quick YouTube search will turn up several – try looking for “saponification“) involve lye. Lye is actually a broad term that covers a couple of different chemicals, but most of the time when people say lye these days, they mean pure sodium hydroxide.

Pure sodium hydroxide is usually supplied as pellets.

Pure sodium hydroxide comes in the form of pellets. It’s dangerous for two reasons. Firstly, precisely because it’s so good at breaking down fats and proteins, i.e. the stuff that humans are made of, it’s really, really corrosive and will give you an extremely nasty burn. Remember that scene in the movie Fight Club? Yes, that scene? Well, that. (Follow that link with extreme caution.)

And secondly, when sodium hydroxide pellets are mixed with water, the solution gets really, really hot.

It doesn’t take a lot of imagination to realise that a really hot, highly corrosive, solution is potentially a huge disaster waiting to happen. So, and I cannot stress this enough, DO NOT attempt to make your own soap unless you have done a lot of research AND you have ALL the appropriate safety equipment, especially good eye protection.

And there we are. Soap is ancient and awesome, and full of interesting chemistry. Make sure you appreciate it every time you wash your hands, which ought to be frequently!

Stay safe, everyone. Take care, and look after yourselves.

Want something non-sciency to distract you? Why not check out my fiction blog: the fiction phial. There are loads of short stories, and even (recently) a poem. Enjoy!

If you’re studying from home, have you got your Pocket Chemist yet? Why not grab one? It’s a hugely useful tool, and by buying one you’ll be supporting this site – it’s win-win!

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2020. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, please consider buying me a coffee through Ko-fi using the button below.
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Refilling bottles: why it may not be as simple as you thought

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Two years or so ago most of us had given relatively little thought to single-use plastics. We bought things, we used things, we put the packaging in the bin. Possibly the recycling bin. Hopefully the right recycling bin. And we thought no more about it.

Then Blue Planet II aired on BBC One, specifically episode 7, and suddenly everyone was obsessed with where all this plastic was ending up. Rightly so, since it was clearly ending up in the wrong places, and causing all sorts of havoc in the process.

People started buying reusable cups, eschewing plastic straws and demanding the option of loose fruit and vegetables in supermarkets. Wooden disposable cutlery, oven-cook food containers, and bamboo straws became increasingly common.

And people started to ask more questions about refilling containers. Why do I need a new bottle each time I buy more shampoo or washing up liquid or ketchup, they asked. Why can’t we just refill the bottle? For that matter, couldn’t I take a container to the shop and just… fill it up?

Infinity Foods allow customers to refill containers.

Shops started to offer exactly that. One such place was Infinity Foods, based in Brighton in the UK. Actually, they’d always taken a strong line when it came to recycling and reducing waste, and had been offering refills of some products for years.

Where this gets interesting from a chemistry point of view is a Facebook post they made at the beginning of this month. It said, from the 1st of November, “your empty bottle can only be refilled with the same contents as was originally intended. This includes different brands and fragrances.”

Naturally this spawned lots of comments, many suggesting the change was “daft” and saying things like “I bet it is major corporations not wanting us to reuse the bottle.”

Infinity Foods argued that they were tightening up their policy in order to comply with legislation, specifically the Classification, Labelling and packaging of substances and mixtures (CLP) Regulation (EC) No 1272/2008 and others.

This post, and the comments, got me thinking. I’m old enough, just, to remember the days when random glass bottles were routinely filled with random substances. You wandered into the garage (it was always the garage) and there’d be something pink, or blue, or green, or yellow in a bottle. And it might have a hand-written label, and it might not, and even if it did, the label wasn’t guaranteed to actually be representative of the contents. The “open it and sniff” method of identification was common. The really brave might take their chances with tasting. Home-brew wine might well be next to the lawnmower fuel, and if they got mixed up, well, it probably wouldn’t be fatal.

Probably.

Bottles may be single-use, but they’ve also been designed to be as safe as possible.

You know, I’m not sure we ought to be keen to go back to that, even if it does save plastic. Sealed bottles with hard-to-remove child safety caps, nozzles that only dispense small amounts (making it difficult if not impossible to drink the contents, by accident or otherwise) and accurate ingredients lists are, well, they’re safe.

And we’ve all grown used to them. Which means that now, if I pick up a bottle, I expect the label to tell me what’s in it. I trust the label. If I went to someone else’s house and found a bottle of, say, something that looked like washing up liquid by the sink, I’d assume it was what the label said it was. I wouldn’t even think to check.

You might think, well, so what? You fill a bottle, you know what’s in it. It’s up to you. But what about all the other people that might come into contact with that bottle, having no idea of its origins? What if a visitor has an allergy to a particular ingredient? They look at the label, check it doesn’t contain that ingredient, and use it. Only, someone has refilled that bottle with something else, and maybe that something else does contain the thing they’re allergic to.

Even simpler, someone goes to a shop that sells refills, fills a hair conditioner bottle with fabric softener and doesn’t think to label it. They know what it is, right? They leave it in the kitchen, someone else picks up that bottle, and takes it into the shower. They get it in their eyes and… maybe it causes real harm.

Toilet cleaner must never be mixed with toilet bleach.

Then there are the very real hazards associated with mixing chemicals. One that always worries me is the confusion between toilet cleaner and toilet bleach. Many people have no idea what the difference is. The bottles even look quite similar. But they are not the same substance. Toilet cleaner is usually a strong acid, often hydrochloric acid, while toilet bleach contains sodium hypochlorite, NaClO. Mixing the two is a very bad idea, because the chemical reaction that occurs produces chlorine gas, which is particularly hazardous in a small, enclosed space such as a bathroom.

Okay, fine, toilet bleach and cleaner, noted, check. Is anyone selling those as refills anyway? Probably not. (Seriously, though, if you finish one bottle, make sure you don’t mix them in the toilet bowl as you open the next.)

But it may not be as straightforward as that. Have you ever used a citrus-scented cleaning product? They can be quite acidic. Combine them with bleach and, yep, same problem. What if someone refilled a container that contained traces of a bleach cleaner with one that was acidic, not realising? Not only would it be harmful to them, it could also be harmful for other people around them, including employees, especially if they suffer from a respiratory condition such as asthma.

There are risks associated with the type of container, too. Some plastics aren’t suitable to hold certain substances. Infinity Foods themselves pointed out that some people were trying to find drinking water bottles and plastic milk bottles with cleaning products. These types of bottles are usually made of high-density polyethylene (HDPE). This type of plastic is a good barrier for water, but not oily substances and solvents. Cleaning products could weaken the plastic, resulting in a leak which would be messy at best, dangerous at worst. That’s before we even think about the (un)suitability of the cap.

The type of plastic used to make water bottles isn’t suitable to hold oily substances.

Plus, think of the poor salesperson. How are they supposed to judge, in a shop, whether a particular bottle is safe for a particular product? I wouldn’t feel at all confident about that decision myself. It’s not even always easy to identify which plastic a bottle is made of, and that’s before you even start to consider the potential risks of mixing substances.

In fact, the more you think about it, the more Infinity Foods’ policy makes sense. If you say that you can only refill a bottle with the exact same substance it originally contained, and you insist that the labels have to match, well, that’s easy to check. It’s easy to be sure it’s safe. Yes, it might mean buying a bottle you wouldn’t have otherwise bought, but if you’re going to reuse it, at least it’s just the one bottle.

These concerns all arise from wanting to make sure the world is a safer and healthy place. We do need to cut down on single-use plastics, but taking risks with people’s health to do so surely misses the point.

Like the Chronicle Flask’s Facebook page for regular updates, or follow @chronicleflask on Twitter. Content is © Kat Day 2019. You may share or link to anything here, but you must reference this site if you do. If you enjoy reading my blog, please consider buying me a coffee through Ko-fi using the button below.
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Toxins and tanks: could your fishtank really be deadly?

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Could a deadly poison be lurking in your fish tank?

A few days ago I came across a news story: “Fish owner tells how cleaning out tank released deadly palytoxin that poisoned family and led to closure of entire street“. Now you have to admit, as titles go that’s pretty compelling.

To begin with, for some reason, I had it in my head that this happened in Australia (in my defence, that is where most of the really deadly stuff happens, right?). But no, this happened in the U.K. Not only that, but it was even in Oxfordshire, which is my neck of the woods.

The fish tank owner, a man named Chris Matthews, was actually an experienced aquarist. He knew about palytoxin – a poisonous substance which can be released by corals – and he was aware that it can be deadly if ingested. He also knew that it can cause serious skin irritation.

What he didn’t realise was that taking his pulsing xenia coral out of the tank could cause it to release the toxin into the air.

But before I talk about palytoxin, let’s just look at the word “toxin” for a moment. It has a specific meaning, and it’s often misused. As in many, many adverts. Here’s a recent one, but these easy to find – just put “toxin free” into the search engine of your choice.

In a way, this is quite funny. You see, “toxin” specifically refers to “a poison of plant or animal origin“. In other words, a naturally occurring poison*. There are lots and lots of naturally occurring poisons. Plants make them all the time, generally to ward off pests. Most essential oils can, at a high enough dose, be toxic. The hand cream in that picture contains peppermint oil. Peppermint is, of course, pretty safe – we’ve all eaten mints after all – but guess what? Take huge dose of it and it becomes a real problem. Now, I’m not for one second suggesting that hand cream is dangerous or harmful, but technically, it’s not “toxin free”.

Beauty products which contain only synthetic ingredients are, by definition, toxin-free.

Yes, the irony or this sort of marketing is that beauty products made out of entirely synthetic ingredients definitely will be toxin-free. Nothing natural = no toxins. Whereas anything made out of naturally occurring substances almost certainly isn’t, regardless of its spurious labelling.

Anyway, back to the palytoxin. It’s naturally occurring. And incredibly dangerous. More proof, as if we needed it, that natural doesn’t mean safe. Very often, in fact, quite the opposite. The human race has spent millenia working out how to protect itself from nature and all her associated nastiness (bacteria, viruses, extreme temperatures, poor food supply, predators…. the list is long and unpleasant) and yet for some reason it’s become fashionable to forget all that and imagine a utopia where mother nature knows best. Honestly, she doesn’t. Well, maybe she does – but being kind to human beings isn’t on her agenda.

Palytoxin is especially unpleasant. Indeed, it’s thought to be the second most poisonous non-protein substance known (there are some very impressive protein-based ones, though – botulinum toxin for one). The only thing which is more toxic is maitoxin – a poison which can be found in striated surgeonfish thanks to the algae they eat.

Palytoxin is a large molecule.

Palytoxin is a big molecule, technically categorised as a fatty alcohol. It has eight carbon-carbon double bonds, 40 hydroxy groups (phew) and is positively covered in chiral centres (don’t worry students: your teacher isn’t going to expect you to draw this one. Probably). Bits of it are water-soluble whilst other parts are fat soluble, meaning it can dissolve in both types of substance. Because it’s not a protein, heat doesn’t denature it, so you can’t get rid of this toxin with boiling water or by heating it. However, it does decompose and become non-toxic in acidic or alkaline solutions. Household bleach will destroy it.

It’s mostly found in the tropics, where it’s made by certain types of coral and plankton, or possibly by bacteria living on and in these organisms. It also turns up in fish, crabs and other marine organisms that feed on these things.

In fact, story time! There is a Hawaiian legend which tells that Maui villagers once caught a Shark God with a hunger for human flesh whom they believed had been killing their fishermen. They killed the Shark God and burned him, throwing the ashes into a tide pool. The ashes caused ugly brown anemones to grow. Later, the villagers discovered that blades smeared with these “limu” would cause certain death. So the anemones came to be known as “Limu Make O Hana” or Seaweed of Death from Hana. We now know that those brown ‘anemones’ are zoanthid corals, and the ‘certain death’ was due to palytoxin poisoning.

Zoanthids are a source of palytoxin.

People don’t suffer palytoxin poisoning very often. Most cases have been in people who’ve eaten seafood and, as here, aquarium hobbyists. In a few cases people have been exposed to algae blooms.

It’s really nasty though. Palytoxin can affect every type of cell in the body (yikes) and as a result the symptoms are different according to the route of exposure. Eat it and you’re likely to experience a bitter taste in your mouth, muscle spasms and abdominal cramps, nausea, lethargy, tingling and loss of sensation, slow heart rate, kidney failure and respiratory distress. It can damage your heart muscle; in the worst case scenario, it causes death by cardiac arrest.

On the other hand, if you inhale it, the symptoms are more likely to revolve around the respiratory system, such as constriction of the airways which causes wheezing and difficulty breathing. It can also cause fever and eye-infection type symptoms. Over time, though, the result is the same: muscle weakness and eventually, death from heart failure.

The respiratory symptoms from palytoxin are easily misdiagnosed: it looks like a viral or bacterial infection. In fact, our fish tank owner initially thought he had flu. It was only when everyone in the family got ill, even the dogs, that he realised that it must be poisoning. Fortunately, the emergency services took it seriously and sent both ambulance and fire crews to his house, as well as police. They closed the street and ensured that the poison was safely removed.

There is no antidote, but the symptoms can be eased by, for example, treatment with vasodilators. If the source of exposure is removed the victim is likely to recover over time. You’ll be pleased to hear that Chris Matthews, his family, and the firefighters who attended the scene, were checked over at hospital and appear to be okay.

If you’re an aquarium owner, how to you avoid getting into this kind of predicament? As Chris Matthews said, the coral he had, pulsing xenia, was “not expensive and a lot of people have it.”

Click the image to read safety guidelines from the Ornamental Aquatic Trade Association.

According to the Ornamental Aquatic Trade Association, the most important piece of safety advice is to only handle your marine creatures underwater and fully submerged. Don’t take them out of the tank unnecessarily, and if you do need to move them, use submerged plastic bags or a bucket, so that they stay underwater at all times. You should also wear strong rubber gloves, ideally gloves specifically designed for aquarium use (such as these). If you need to dispose of a rock which contains soft coral species, soak it in a bleach solution – one part household bleach to nine parts water – for several days before you intend to dispose of it. Leaving an untreated rock outside to dry will not make it safe – it could still be highly toxic. Finally, whilst activated charcoal can help to keep palytoxin out of the water, it may not be able to cope with large quantities, and it needs to be changed frequently.

Fish tank owner Chris also said: “The information is not readily available online in a way people can easily understand” and “I want to use this experience to educate people about the risks and the measures people need to take.” Hopefully this blog post (and all the associated news coverage) will help with that. Be careful with your corals!

* Note that while ‘toxin’ specifically refers to poisonous substances from plants and animals, this restriction doesn’t extend to the word “toxic”. The definition of that is “containing or being poisonous material” (regardless of whether it’s a naturally-occurring substance or not). So “non-toxic” labels are fine, if a little bit meaningless – no matter what the woo-pushing sites say, your hand cream really isn’t poisonous.

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Hydrogen peroxide: another deadly alternative?

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I’m sure most people have heard of hydrogen peroxide. It’s used as a disinfectant and, even if you’ve never used it for that, you probably at least know that it’s used to bleach hair. It’s where the phrase “peroxide blonde” comes from, after all. Hydrogen peroxide, and its formula, is so famous that there’s an old chemistry joke about it:

(I have no idea who to credit for the original drawing – if it’s you, leave me a message.)

To save you squinting at the text, it goes like this:
Two men walk into a bar. The first man says, “I’ll have some H2O.”
The second man says, “I’ll have some H2O, too.”
The barman brings the drinks. The second man dies horribly.

Now I think about it, it’s not a terribly funny joke.

Hydrogen peroxide has an extra oxygen atom in the middle.

Never mind. You get the idea. H2O2 (“H2O, too”) is the formula for hydrogen peroxide. Very similar to water’s formula, except with an extra oxygen atom in the middle. In fact, naturopaths – purveyors of alternative therapies – often refer to hydrogen peroxide as “water with extra oxygen”. But this is really misleading because, to torture a metaphor, that extra oxygen makes hydrogen peroxide the piranha to water’s goldfish.

Water, as we know, is pretty innocuous. You should try not to inhale it obviously, or drink more than about six litres in one go, but otherwise, its pretty harmless. Hydrogen peroxide, on the other hand, not so much. The molecule breaks apart easily, releasing oxygen. That makes it a strong oxidising agent. It works as a disinfectant because it basically blasts cells to pieces. It bleaches hair because it breaks down pigments in the hair shaft. And, as medical students will tell you, it’s also really good at cleaning up blood stains – because it oxidises the iron in haemoglobin to Fe3+, which is a pale yellow colour*.

Dilute hydrogen peroxide is readily available.

In its dilute form, hydrogen peroxide is a mild antiseptic. Three percent and even slightly more concentrated solutions are still readily available in high-street pharmacies. However, even these very dilute solutions can cause skin and eye irritation, and prolonged skin contact is not recommended. The trouble is, while it does destroy microbes, it also destroys healthy cells. There’s been a move away from using hydrogen peroxide for this reason, although it is still a popular “home” remedy.

More concentrated** solutions are potentially very dangerous, causing severe skin burns. Hydrogen peroxide is also well-known for its tendency to react violently with other chemicals, meaning that it must be stored, and handled, very carefully.

All of which makes the idea of injecting into someone’s veins particularly horrific.

But this is exactly what some naturopaths are recommending, and even doing. The idea seems to have arisen because hydrogen peroxide is known to damage cancer cells. But so will a lot of other dangerous substances – it doesn’t mean it’s a good idea to inject them. Hydrogen peroxide is produced by certain immune cells in the body, but only in a very controlled and contained way. This is definitely a case where more isn’t necessarily better.

The use of intravenous hydrogen peroxide appears to have begun in America, but it may be spreading to the UK. The website yestolife.org.uk, which claims to empower people with cancer to “make informed decisions”, states “The most common form of hydrogen peroxide therapy used by doctors calls for small amounts of 30% reagent grade hydrogen peroxide added to purified water and administered as an intravenous drip.”

30% hydrogen peroxide is really hazardous stuff. It’s terrifying that this is being recommended to vulnerable patients.

Other sites recommend inhaling or swallowing hydrogen peroxide solutions, both of which are also potentially extremely dangerous.

If anyone ever suggests a hydrogen peroxide IV, run very fast in the other direction.

In 2004 a woman called Katherine Bibeau died after receiving intravenous hydrogen peroxide treatment from James Shortt, a man from South Carolina who called himself a “longevity physician”. According to the autopsy report she died from systemic shock and DIC – the formation of blood clots in blood vessels throughout the body. When her body arrived at the morgue, she was covered in purple-black bruises.

Do I need to state the obvious? If anyone suggests injecting this stuff, run. Run very fast, in the other direction. Likewise if they suggest drinking it. It’s a really stupid idea, one that could quite literally kill you.

* As anyone who’s ever studied chemistry anywhere in my vicinity will tell you, “iron three is yellow, like wee.”

** The concentration of hydrogen peroxide is usually described in one of two ways: percentage and “vol”. Percentage works as you might expect, but vol is a little different. It came about for practical, historical reasons. As Prof. Poliakoff comments in this video, hydrogen peroxide is prone to going “flat” – leave it in the bottle for long enough and it gradually decomposes until what you actually have is a bottle of ordinary water. Particularly in the days before refrigeration (keeping it cold slows down the decomposition) a bottle might be labelled 20%, but actually contain considerably less hydrogen peroxide.

What to do? The answer was quite simple: take, say, 1 ml of hydrogen peroxide, add something which causes it to decompose really, really fast (lots of things will do this: potassium permanganate, potassium iodide, yeast, even liver) and measure the volume of oxygen given off. If your 1 ml of hydrogen peroxide produces 10 ml of oxygen, it’s 10 vol. If it produces 20, it’s 20 vol. And so on. Simple. 3% hydrogen peroxide, for the record, is about 10 vol***. Do not mix up these numbers.

*** Naturally, there are mole calculations to go with this. Of course there are. For A-level Chemists, here’s the maths (everyone else can tune out; I’m adding this little footnote because I found this information strangely hard to find):

Hydrogen peroxide decomposes as shown in this equation:
2H2O2 –> 2H2O + O2

Let’s imagine we decompose 1 ml of hydrogen peroxide and obtain 10 mls of oxygen.

Assuming the oxygen gas occupies 24 dm3 (litres), or 24000 mls, at standard temperature and pressure, 10 mls of oxygen is 10 / 24000 = 0.0004167 moles. But, according to the equation, we need two molecules of hydrogen peroxide to make one molecule of oxygen, so we need to multiply this number by two, giving us 0.0008333 moles.

To get the concentration of the hydrogen peroxide in the more familar (to chemists, anyway) mol dm-3, just divide that number of moles by the volume of hydrogen peroxide. In other words:

0.0008333 mols / 0.001 dm3 = 0.833 mol dm-3

If you really want to convert this into a percentage by mass (you can see why people stick with “vol” now, right?), then:

0.833 mol (in the litre of water) x 34 g mol-1 (the molecular mass of H2O2)
= 28.32 g (in 1000 g of water)

Finally, (28.32 / 1000) x 100 = 2.8% or, rounding up, 3%

In summary (phew):
10 vol hydrogen peroxide = 0.83 mol dm-3 = 3%

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Black Salve BS

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Historically, people weren’t always careful in the sun.

Summer is fast disappearing in the Northern hemisphere and with it, the sunshine. Which is sad, as we all love a bit of sun, don’t we? Even if it doesn’t always love us, particularly those of us with fairer skin. Sunburn is no fun, but these days we also understand that it’s worse than a couple of days of painfully peeling skin: too much sun exposure can cause cancer.

Unfortunately there’s a whole generation – indeed more than one – who didn’t grow up with parents constantly slathering on the factor 50 (easy-to-use transparent sunscreens with very high SPFs didn’t appear on the market until the 1990s). For some sunburn was a regular part of summer, and those people need to be particularly vigilant for changes which might signify something nasty is going on.

On the plus side, these types of cancer are very treatable, and the outlook is hopeful. Often, the growth can be removed by surgery or even cryotherapy with very little scarring. Even the most dangerous kind of skin cancer, malignant melanoma, has a ten-year survival rate of around 90% with appropriate treatment.

But there’s the key: appropriate treatment. If you notice changes in your skin, especially a mole which is changing in colour or shape, you must see a qualified doctor as soon as you can.

What you should absolutely not do is visit the Black Salve page on Facebook (which I am not linking to for reasons which will be come obvious). This page, so Facebook tells me, is followed by nearly 17,000 users. It features a cheery cover photo of a family holding a canoe over their heads, and its profile picture is a pretty white and yellow flower.

Sanguinarine is a toxic salt extracted from the bloodroot plant. It’s infamous for its ability to destroy animal cells.

It’s all very suggestive of a homely, traditional remedy. The sort of thing your grandma had in her medicine cabinet. Very safe and “natural“. But while black salve might be a traditional remedy, it is anything but safe. Most preparations contain bloodroot, a source of the toxin sanguinarine, which kills animal cells.

Applying bloodroot to the skin destroys tissues and causes the formation of a large, black lump of dead flesh. Eventually this mass, called an eschar, falls off, leaving varying degrees of damage behind (internal use is also not recommended: consuming bloodroot can cause vomiting and loss of consciousness).

Bloodroot is easy to buy. Back in May this year the Good Thinking Society reported that eBay had removed “listings for dangerous cancer ‘cure’” following an investigation. Those listings were for black salve, and this was, of course, very positive news. Except for one thing: whilst listings for black salve were removed (and remain absent), listings for bloodroot were not. At the time of writing, a quick search reveals several bloodroot preparations still for sale.

At the time of writing, bloodroot is easy to find on eBay. The listing confirms that this is prepared from the “rhizome of certified organically grown Sanguinaria conadensis plants”.

Why is this such a bad thing? Because it’s easy to find recipes for making homemade black salve with bloodroot online, and using such mixtures can have truly horrific consequences. Last year the story of a woman who applied it to a basal cell carcinoma on her nose was widely reported. The black salve paste she used did so much damage that she ended up with a large hole in her nose through which she could actually draw air. Photos and video are available online (be warned: it’s gruesome).

Many patients turn to black salve as an alternative to what they imagine will be disfiguring surgery to treat their cancer. But, as in this woman’s case, the paste can do so much damage that far more extensive, reconstructive, surgery is ultimately needed.

Black Salve usually contains bloodroot and, sometimes, zinc chloride – another skin irritant.

It won’t surprise anyone to learn that dermatologists don’t recommend black salve. It can do enormous damage to the surface of the skin, resulting in scarring and a high risk of infection, and it does kill cancer cells along the way. But there is no guarantee that all of the cancerous cells deep within the skin will be destroyed. As a result, patients who’ve attempted to cure themselves may end up with cancerous tissue hidden, and growing, beneath a scar.

In fact, exactly this happened to an otherwise healthy 76 year-old woman in 2006. Her case is described in detail in the journal Dermatology Practical Conceptual – in summary, she refused surgery on a small melanoma on her leg. Instead, she bought black salve on the internet and applied it. A few years later the cancer had spread to her lungs, liver and lymph nodes.

Some people even recommend using black salve on breast cancers but this is, if possible, even worse. It’s highly unlikely that the salve will reach the entirety of a tumour which is beneath the skin. It is likely to do some horribly painful and disfiguring damage along the way, though.

Black salve is particularly popular in Australia, which of course has some of the highest rates of skin cancer in the world. But it’s available in the UK too. One online “herbal medicine” site is openly selling various formulations at prices ranging from £25-£100. Ironically, they describe their “Herbactive” product as “chemical free” (it isn’t, nothing is) and then go onto boast that it “now has a stronger concentration of bloodroot”. Fantastic.

They also sell a product which contains zinc chloride along with bloodroot. They claim zinc chloride is safe. It isn’t. It’s well-known to be a skin irritant, and should never be left in contact with skin.

The Black Salve Facebook page is full of anecdotes and testimonials, but light on evidence.

The Black Salve Facebook page is packed full of anecdotes and testimonials from people who claim to have used these mixtures safely. It’s all interspersed, of course, with the usual “Big Pharma” conspiracy theories. Namely, that the “truth” is being suppressed because there’s “no money in it for the pharmaceutical [industry].”

The irony is that reconstructive surgery is incredibly expensive, and the antibiotics, painkillers and other drugs that are inevitably needed to treat black salve victims aren’t free, either.

Given that Facebook’s community standards page states that: “We remove content, disable accounts and work with law enforcement when we believe that there is a genuine risk of physical harm or direct threats to public safety.” one has to wonder why the Black Salve page is still there. People are actually posting pictures of physical harm. What more does Facebook need?

Please, don’t be tempted to use black salve, or anything containing bloodroot. If you think you have a skin tumour see a properly qualified doctor and follow his or her advice.

It might literally save your life.

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Hazardous homeopathy: ‘ingredients’ that ought to make you think twice

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Would you take a medicine made with arsenic? Or deadly nightshade? Lead? Poison ivy?

You’d ask some serious questions first, at least, wouldn’t you? Is it definitely safe? Or, more accurately, are the odds better than even that it will make me better without causing horrible side-effects? Or, you know, killing me?

There ARE medicines that are legitimately made from highly toxic compounds. For example, the poison beloved of crime writers such as Agatha Christie, arsenic trioxide, is used to treat acute promyelocytic leukemia in patients who haven’t responded to other treatments. Unsurprisingly, it’s not without risks. Side-effects are unpleasant and common, affecting about a third of patients who take it. On the other hand, acute promyelocytic leukemia is fatal if untreated. A good doctor would talk this through with a patient, explain both sides, and leave the final choice in his or her properly-informed hands. As always in medicine, it’s a question of balancing risks and benefits.

Would you trust something with no proven benefit and a lot of potential risk? There are, it turns out, a swathe of entirely unregulated mixtures currently being sold in shops and online which clearly feature the substances I listed at the beginning. And more. Because they are all, supposedly, the starting materials in certain homeopathic remedies.

Homeopaths like to use unfamiliar, usually Latin-based, names which somewhat disguise the true nature of their ingredients. Here’s a short, but by no means comprehensive, list. (You might find remedies labelled differently but these are, as far as I can tell, the most common names given to these substances.)

If you haven’t heard of some of these, I do urge you to follow the links above, which will largely take you pages detailing their toxicology. Spoiler: the words “poison”, “deadly” and “fatal” feature heavily. These are nasty substances.

There are some big ironies here, and I’m not referring to the metal. For example, a common cry of anti-vaccinationists is that vaccines contain animal tissues – anything and everything from monkey DNA to dog livers. But many also seem to be keen to recommend homeopaths and courses of homeoprophylaxis – so-called “homeopathic vaccines” – which use bodily fluids such as pus and blood as starting materials.

Now, at this point I’m sure some of you are thinking, hang on a minute: aren’t you always telling us that “the dose makes the poison“? And aren’t homeopathic remedies diluted so much that none of the original substance remains, so they’re just placebos?

Yes, I am, and yes, they are.

Does anyone test homeopathic remedies to make sure there’s nothing in them….?

In THEORY. But here’s the problem: who’s testing these mixtures to make sure that the dilutions are done properly? And how exactly are they doing that (if they are)?

One technique that chemists use to identify tiny quantities of substance is gas chromatography (GC). This is essentially a high-tech version of that experiment you did at school, where you put some dots of different coloured ink on a piece of filter paper and watched them spread up the paper when you put it in some water.

GC analysis is brilliant at identifying tiny quantities of stuff. 10 parts per million is no problem for most detectors, and the most sensitive equipment can detect substances in the parts per billion range. Homeopathy dilutions are many orders of magnitude higher than this (30c, for example, means a dilution factor of 1060), but this doesn’t matter – once you get past 12c (a factor of 1024) you pass the Avogadro limit.

This is because Avogadro’s number, which describes the number of molecules in what chemists call a “mole” of a substance, is 6×1023. For example, if you had 18 ml of water in a glass, you’d have 6×1023 molecules of H2O. So you can see, if you’ve diluted a small sample by a factor of 1024 – more than the total number of molecules of water you had in the first place – the chances are very good that all you have is water. There will be none of the original substance left. (This, by the way, is of no concern to most homeopaths, who believe that larger dilutions magically produce a stronger healing effect.)

What if the sample ISN’T pure water after it’s been diluted?

If you carried out GC analysis of such a sample, you should find just pure water. Indeed, if you DIDN’T find pure water, it should be cause for concern. Potassium cyanide, for example, is toxic at very low levels. The lethal dose is is only 0.2-0.3 grams, and you’d suffer unpleasant symptoms long before you were exposed to that much.

So what if the dilutions somehow go wrong? What if some sample gets stuck in the bottle? Or on the pipette? Or a few dilution steps get skipped for some reason?

Are these largely unregulated companies rigorously quality-checking their remedies?

Well, maybe. It’s possible some producers are testing their raw materials for purity (ah yes, another question: they CLAIM they’re starting with, say, arsenic, but can we be certain?), and perhaps testing the “stability” of their products after certain periods of time (i.e. checking for bacterial growth), but are they running tests on the final product and checking that, well, there’s nothing in it?

And actually, isn’t this a bit of a conflict? If the water somehow “remembers” the chemical that was added and acquires some sort of “vibrational energy”, shouldn’t that show up somehow in GC analysis or other tests? If your tests prove it’s pure water, indistinguishable from any other sample of pure water, then… (at this point homeopaths will fall back on arguments such as “you can’t test homeopathy” and “it doesn’t work like that”. The name for this is special pleading.)

A warning was issued in the U.S. after several children became ill.

Am I scaremongering? Not really. There’s at least one published case study describing patients who suffered from arsenic poisoning after using homeopathic preparations. In January this year the U.S. Food and Drug Administration issued a warning about elevated levels of belladonna (aka deadly nightshade) in some homeopathic teething products. Yes, teething products. For babies. This warning was issued following several reports of children becoming ill after using the products. The FDA said that its “laboratory analysis found inconsistent amounts of belladonna, a toxic substance, in certain homeopathic teething tablets, sometimes far exceeding the amount claimed on the label.”

Now, admittedly, I’m based in the U.K. and these particular teething remedies were never readily available here. But let’s just type “homeopathy” into the Boots.com (the British high-street pharmacy) website and see what pops up… ah yes. Aconite Pillules, 30c, £6.25 for 84.

What happens if you search for “homeopathy” on the Boots.com website?

Have you been paying attention lovely readers? Aconite is…. yes! Monkshood! One of the most poisonous plants in the garden. Large doses cause instant death. Smaller doses cause nausea and diarrhea, followed by a burning and tingling sensation in the mouth and abdomen, possibly muscle weakness, low blood pressure and irregular heartbeat.

I must stress at this point that there is no suggestion, absolutely none whatsoever, that any of the products for sale at Boots.com has ever caused such symptoms. I’m sure the manufacturers check their preparations extremely carefully to ensure that there’s absolutely NO aconite left and that they really are just very small, very expensive, sugar pills.

Well, fairly sure.

In summary, we seem to be in a situation where people who proclaim that rigorously-tested and quality-controlled pharmaceuticals are “toxic” also seem to be happy to use unregulated homeopathic remedies made with ACTUALLY toxic starting materials.

I wonder if the new “documentary” about homeopathy, Just One Drop, which is being screened in London on the 6th of April will clarify this awkward little issue? Somehow, I doubt it. Having watched the trailer, I think it’s quite clear which way this particular piece of film is going to lean.

One last thing. Some homeopathic mixtures include large quantities of alcohol. For example, the Bach Original Flower Remedies are diluted with brandy and contain approximately 27% alcohol (in the interests of fairness, they do also make alcohol-free versions of some of their products and, as I’ve recently learned, they may not be technically homeopathic). Alcohol is a proven carcinogen. Yes, I know, lots of adults drink moderate quantities of alcohol regularly and are perfectly healthy, and the dose from a flower remedy is minuscule, but still, toxins and hypocrisy and all that.

There are cheaper ways to buy brandy than Bach Flower Remedies.

Amusingly, the alcohol in these remedies is described an “inactive” ingredient. It’s more likely to be the only ACTIVE ingredient. And since Flower Remedies retail for about £7 for 20 ml (a mighty £350 a litre, and they’re not even pure brandy) may I suggest that if you’re looking for that particular “medicine” you might more wisely spend your money on a decent bottle of Rémy Martin?

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Is acrylamide in your toast really going to give you cancer?

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Acrylamide has been in the news today, and this might be the understatement of the year. Front page newspaper headlines have been yelling everything from “Brits officially warned off chips” to “Over-cooked potatoes and burnt toast could cause cancer” to the marginally more restrained “What is the real cancer risk from eating roast potatoes or toast?” All this has been accompanied by radio interviews with everyone from actual scientists to professional chefs to people keen to share their roast potato recipes. I expect there have been television interviews too – I haven’t had a chance to watch.

Hey, what could be more traditional, or more fun, than a food-health scare in January?

Acrylamide

Acrylamide

Never fear, the Chronicle Flask is here to sort out the science. Let’s get to the facts: what is acrylamide?

It’s actually a rather small molecule, and it falls into a group of substances which chemists call amides. Other well-known amides include paracetamol and penicillin, and nylon is a polyamide – that is, lots of amide molecules joined together. Amide linkages (the CO-NH bit) are a key feature of proteins, which means they appear in all kinds of naturally-occurring substances.

And this is where the food-acrylamide link comes in. Because acrylamide, or prop-2-enamide to give it its official name (the one only ever used by A-level chemistry students), forms when certain foods are cooked.

Acrylamide occurs naturally in fried, baked, and roasted starchy foods.

Acrylamide occurs naturally in fried, baked, and roasted starchy foods.

It begins with an amino acid called asparagine. If you’re wondering whether, with that name, it has anything to do with asparagus, you’d be on the right track. It was first isolated in the early 1800s from asparagus juice. It turns out to be very common: it’s found in dairy, meat, fish and shellfish, as well as potatoes, nuts, seeds and grains, amongst other things.

This is where the trouble begins. When asparagine is combined with sugars, particularly glucose, and heated, acrylamide is produced. The longer the food is heated for, the more acrylamide forms. This is a particular issue with anything wheat or potato-based thanks to the naturally-occurring sugars those foods also contain – hence all the histrionics over chips, roast potatoes and toast.

How dangerous is acrylamide? The International Agency for Research on Cancer have classified it as a Group 2A carcinogen, or a “probable” carcinogen. This means there’s “limited evidence” of carcinogenicity in humans, but “sufficient evidence” of carcinogenicity in experimental animals. In other words (usually) scientists know the thing in question causes cancer in rats – who’ve generally been fed huge amounts under strictly controlled conditions – but there isn’t any clear evidence that the same link exists in humans. It’s generally considered unethical to lock humans in cages and force feed them acrylamide by the kilo, so it’s tricky to prove.

screen-shot-2017-01-23-at-22-10-46At this point I will point out that alcoholic beverages are classified as Group 1 carcinogens, which means there is “sufficient evidence” of carcinogenicity in humans. Alcohol definitely causes cancer. If you’re genuinely concerned about your cancer risk, worry less about the roast potatoes in your Sunday roast and more about the glass of wine you’re drinking with them.

But back to acrylamide. In animals, it has been shown to cause tumours. It’s one of those substances which can be absorbed through the skin, and after exposure it spreads around the body, turning up in the blood, unexposed skin, the kidneys, the liver and so on. It’s also been shown to have neurotoxic effects in humans. BUT, the evidence that it causes cancer in humans under normal conditions isn’t conclusive. A meta-analysis published in 2014 concluded that “dietary acrylamide is not related to the risk of most common cancers. A modest association for kidney cancer, and for endometrial and ovarian cancers in never smokers only, cannot be excluded.” 

The dose makes the poison is an important principle in toxicology (image credit: Lindsay Labahn)

The dose makes the poison (image credit: Lindsay Labahn)

As I so often find myself saying in pieces like this: the dose makes the poison. The people who have suffered neurotoxic effects from acrylamide have been factory workers. In one case in the 1960s a patient was handling 10% solutions of the stuff, and “acknowledged that the acrylamide solution frequently had splashed on his unprotected hands, forearms and face.” The earliest symptom was contact dermatitis, followed by fatigue, weight loss and nerve damage.

Because of these very real risks, the Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set occupational exposure limits at 0.03 mg/m3 over an eight-hour workday, or 0.00003 g/m3.

Let’s contrast that to the amount of acrylamide found in cooked food. The reason all this fuss erupted today is that the Food Standards Agency (FSA) published some work which estimated the amounts of acrylamide people are likely to be exposed to in their everyday diet.

The highest concentrations of acrylamide were found in snacks (potato crisps etc), and they were 360 μg/kg, or 0.00036 g/kg or, since even the most ardent crisp addict doesn’t usually consume their favoured snacks by the kilo, 0.000036 g/100g. (Remember that those occupational limits are based on continuous exposure over an eight-hour period.)

In other words, the amounts in even the most acrylamide-y of foodstuffs are really quite tiny, and the evidence that acrylamide causes cancer in humans is very limited anyway. There is some evidence that acrylamide accumulates in the body, though, so consuming these sorts of foods day in and day out over a lifetime could be a concern. It might be wise to think twice about eating burnt toast every day for breakfast.

Oh yes, and there’s quite a lot of acrylamide in cigarette smoke. But somehow I doubt that if you’re a dedicated smoker this particular piece of information is going to make much difference.

As the FSA say at the end of their report:

Your toast almost certainly isn't going to kill you.

Your toast almost certainly isn’t going to kill you.

“The dietary acrylamide exposure levels for all age classes are of possible concern for an increased lifetime risk of cancer. The results of the survey do not increase concern with respect to acrylamide in the UK diet but do reinforce FSA advice to consumers and our efforts to support the food industry in reducing acrylamide levels.”

This is not, I would suggest, QUITE the same as “Crunchy toast could give you cancer, FSA warns” but, I suppose, “FSA says risk hasn’t really changed” wouldn’t sell as many newspapers.

One last thing, there’s acrylamide in coffee – it forms when the beans are roasted. There’s more in instant coffee and, perhaps counterintuitively, in lighter-roasted beans. No one seems to have mentioned that today, possibly because having your coffee taken away in January is just too terrifying a prospect to even contemplate. And also perhaps because coffee seems to be associated with more health benefits than negatives. Coffee drinkers are less likely to develop type 2 diabetes, Parkinson’s disease, dementia, suffer fewer cases of some cancers and fewer incidences of stroke. Whether the link is causal or not isn’t clear, but coffee drinking certainly doesn’t seem to be a particularly bad thing, which just goes to show that when it comes to diet, things are rarely clearcut.

Pass the crisps, someone.

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