11 Chemistry Tattoo Fails

Schadenfreude is a German word meaning “pleasure derived from the misfortune of others” and a word whose counterpart is missing from the English language. Although I am sure we would never admit in public to taking pleasure form others’ misfortunes, the awful truth is we all secretly snigger when we see bad things happening to others. This is probably why sites like Fail Blog have become so popular in recent years, forever immortalising the failures of people so future generations can appreciate them.

As awful as this sounds, in the past I got my fix of schadenfreude from pictures of people who have decided to get a tattoo of Japanese text on their body without first checking the translation. What these people end up with is a tattoo that arguably looks cool but once it’s translated, makes them look like a complete plonker. Take, for example, the picture below of a guy who got  “Baka gaijin” tattooed on his back which, as someone who has been to Japan and has been called it knows, it means “stupid foreigner”.

baka-gaijin

Unfortunately the rise in popularity of these fail pictures has led to the youth of today checking the translation before having it permanently tattooed on their body; starving us of our much needed schadenfreude. There is, however, a type of tattoo that still to this day is plagued with errors that not many people are aware of. This type of tattoo is also an excellent source of schadenfreude, as the only people who seem to get them are either those who want to seem more intelligent to their peers or undergraduates who think they know more than they actually do, and will regret their decision once they get to second year and realise their mistake. I am of course talking about those who have decided to get tattoos of a structural formula.

Structural formulas are graphical representations of molecules showing how the atoms within are arranged. What’s important to know is that everything in these diagrams has a meaning – the thickness of a line, how many lines there are between two points, the angle of these lines, etc.  and if you were to get any of these things wrong, the whole structure is wrong. As you can imagine, mistakes are easy to make, but you would think if you were going to get it permanently put on your body you would get it first checked by a chemist.  Fortunately for horrible people like myself, this is not the case with about 1 out of every 4 structural formula tattoos I saw online containing at least one error.

Let’s start off slow with this tattoo of dopamine, serotonin and the elements symbols for thorium, indium, and potassium. The first thing that really jumps out is that all the letters in the element symbols are capitalised which could have been corrected by simply looking at any periodic table on the planet. Next, let’s move on to the lower structure which I think is meant to be dopamine but, because it is missing a double bond in its ring, this is a completely different molecule. Last is the top molecule which is meant to be serotonin, but the indole component is completely the wrong shape making the five-membered nitrogen-containing pyrrole ring look hexagonal. The position of the NH with the hydrogen to the right of the nitrogen within what is meant to be the ring structure turns into the para hydrogen on the now phenol ring leaving a floating nitrogen on the other side.

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Here we have another example where we have inconsistent line thickness and now two dubble bonds missing from dopamine.

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Next we have yet another example of a dopamine serotonin combination tattoo and although they have corrected the dopamine mistakes they have buggered up serotonin by removing the nitrogen from the pyrrole ring and replacing it with carbon and having a magical NH group floating in mid-air. They have also decided to draw the primary amine upside-down.

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The next person in this list for some unknown reason decided to brand themselves with what I believe was meant to be MDMA – also known as ecstasy. Looking past why on Earth anyone would want to promote their recreational drug use to the world, you can see that they have drawn the wrong structure.

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When it comes to ball and stick representations of molecules, each different atom is distinguished from another by a different colour. Here, we have what I think is meant to be DMT but with the mismatch of colours could be anything.

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The next person on this list must have been high when they thought it would be a good idea to have one of the main psychoactive compounds (THC) found in cannabis tattooed on them with magical hypervalent oxygens instead of methyl groups.

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Here we have a tattoo of the psychedelic drug lysergic acid diethylamide also known as LSD that is missing the diethylamide!

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This arsehole is also missing the diethylamide as they forgot to put in the nitrogen.

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This one is a little harder to see, as it revolves around the stereochemistry of DXM. The first problem is the lack of either a dashed or wedged line going from the chiral carbon in the middle of the compound connected to the hydrogen. Without indicating which way this hydrogen is pointing, it is pointless having it there. Second is the nitrogen containing ring that is clearly in front of the rest of the molecules because of the break in the cyclohexane ring behind it. This is the wrong isomer of DXM and therefore the wrong compound.

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Here is another example of a stereochemistry fail. This person has also decided to brand themselves with THC, only they have decided that they prefer the compound the other way round. The reason we know this is the case, rather than the image having simply been flipped, is that the methyl groups have been marked as “Me”. Unfortunately, when you flip the molecule, the parts that were originally facing towards you are now facing away – something this person did not realise.

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It’s kind of hard to know where to start on the next one because there is so much wrong with it. The removal of nearly all double bonds, the carbon-carbon bond between LSD and THC, the substitution of oxygen with carbon on the THC – to name just a few!

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Believe me when I say I have barely scratched the surface! You will be shocked about the amount of chemistry tattoos with errors in them. Yes, the majority of these mistakes have to do with the shape of the molecule and their bond angles… but if you are going to have this structure permanently on your flesh, you would want to make sure it was 100% accurate.

At this point I would offer my services, but then where would I get my Schadenfreude fix from?! So instead I am going to, every now and again, jump online and derive pleasure from people who don’t know they have made fools of themselves.

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About Myles Power (595 Articles)
My name is Myles Power, and I run the educational YouTube channel, powerm1985. I spend what little free time I have sharing my love of SCIENCE! through home experiments, visiting sites of scientific interest, and angrily ranting at pseudoscience proponents. I am also one of the founding members of the podcast 'The League of Nerds' - which I co-host with James from 'The History of Infection'.

3 Comments on 11 Chemistry Tattoo Fails

  1. So I want a tattoo of oxytocin. How do I make sure it’s correct? It would go from the left side of my chest to the center of my chest with the widest part of oxytocin being on the outer part. Does the image need to be flipped or will it be correct for someone looking straight at me? Obviously asking so I don’t end up like one of these people

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  2. Riley Risteen // May 7, 2017 at 4:32 pm // Reply

    I always wondered why the hell non-scientists would get a chemical structure tattooed on themselves.
    For non-scientists it is a trend, and will end up just being confusing later on in life. It is analogous to someone getting a tattoo of the Jedi symbol to represent balance, morality, and discipline, despite never seeing the Star Wars movies.
    Getting a molecule tattoo represents more than just whatever that molecule is; it also represents a dedication to science.

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  3. You spelled double dubble…

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