— Technicals Logo
We had an email from a Chemistry World reader called Joey this morning, wondering about the logo on the ‘Technicals’ range of clothing at UK outdoors equipment shop Blacks.
The logo resembles a chemical structure, but it’s not entirely clear what the significance (if any) of such a molecule might be. Anyone out there have any ideas – the structure is a miss on Chemspider, but it might be worth running it through SciFinder or some other such database.
Joey, in his quest for an explanation, has apparently asked various university lecturers, school chemistry teachers, technicians and even Blacks head office but no-one is able to agree on what the structure is. He suggests it may be stylised, with some functional groups omitted for ‘design purposes’ but we’d love to know what you all think.
Happy hunting!
Phillip Broadwith
Update 4 June 2010.
Well, the general concensus so far seems to be that it is some kind of stylised neurochemical – @Stuartcantrill and @gingerbreadlady on twitter suggested it might be a layman’s adrenaline, which would fit more sensibly with the company making sports-related clothing, but the structure doesn’t really fit.
Rich Apodaca in the comments below suggested it might be an amphetamine-based metabolite of Ecstasy (3,4-methylenedimethoxymethamphetamine, MDMA) which is a better fit for the structure, but begs the question of why it’s appearing on Blacks jumpers and jackets…
Maybe we’re all missing something – maybe the Blacks designers are closet ravers, or maybe someone just doodled some geometric lines and thought – ‘that looks a bit “technical”, let’s use that…’
Reaxys returns no hits
Although the atom labels are missing, given the context I believe the figure is depicting an analog of Ecstasy (MDMA) called “DMMA” – or 3,4,-dimethoxymethamphetamine.
Chempedia lists each enantiomer here:
http://chempedia.com/substances/9-0983-6263-8315
and here:
http://chempedia.com/substances/1-0207-2071-9879
A 2007 study looked at the relative potencies of several MDMA analogs including DMMA at the noradrenaline and serotonin transporters (two sites of activity for Ecstasy):
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2095113/
I’m no organic chemist so I won’t embarrass myself by giving it a name. I do wonder, however, if anyone at Blacks noticed that this doesn’t look like the most stable form of this molecule, sterically-speaking… I guess it depends on the ring’s conformation too.
Personally I think it looks like a duck bending over to eat something.
Let’s try that again… my previous comment was off by two methyl groups.
Although the atom labels are missing, I think the structure is HMMA (3,4,-dihydroxymethamphetamine), a metabolite of Ecstasy (MDMA).
Chempedia lists each enantiomer as:
http://chempedia.com/substances/9-5434-6354-6190
and:
http://chempedia.com/substances/5-5831-9019-4737
A 2001 study looked at the quantification of this metabolite in the plasma and urine of MDMA users:
http://pubs.acs.org/doi/abs/10.1021/tx010051p
One more minor correction (too early in the morning for chemistry, apparently)…
The abbreviation for the structure is HHMA.
Hi there,
I’m the Joey who submitted the ‘name that molecule’ molecule. Thank you to all those people who have submitted ideas as to the identity of what this molecule might be.
I’m beginning to doubt whether this actually exists! Having done a bit of toxicology in the past my initial thought was that of Rich Apodaca in so much as it could be an analog of MDMA.
My reasoning for this (other than the very similar structure) is that ecstasy acts as a stimulant and the Technicals clothing was originally designed for mountain rescue teams (apparantly).
Putting these two together I concluded that if it’s cold, wet and windy in the middle of the night mountain rescuers may be thankful for an ecstasy pill to keep them functioning.
Of course, this is just a thought and I am no way suggesting our mountain rescue teams are drug addicts or that the Blacks company are a drug cartel!
Still, if you have any other ideas please post them up here – I’m intrigued to discover the other theories out there…
Thanks again,
Joey
I would tend to agree with the other posts regarding the molecule being a metabolite of MDMA
@Jon-as the drawing is 2d it does look as though it is a relatively sterically hindered molecule, however, if you consider the two carbon atoms along the sidearm attached directly to the benzene ring (see structure of HHMA)which are sp3 hybridised. They are free to rotate and would be arranged in a lower energy conformation in a 3d structure.
I’m fairly sure the molecule is noradrenaline without the stereochemistry. Might be a bit more tasteful for Black’s to put up a structure of the major ‘fight or flight’ neurotransmitter rather than an MDMA metabolite.
http://en.wikipedia.org/wiki/Norepinephrine
whoops. mistake =(
Just encountered this web page. As a retired polymer chemist I have also puzzled over the logo. An aliphatic or aromatic hydrocarbon seems a rather inactive compound in this context so, as others have done, let’s assume some heteroatoms – keep it simple and go for a 1,2-hydroxybenzene (catechol) derivative. The 4-alkyl catechols, such as this, have a bacteriocidal activity. Could it be an additive to keep the smell down when you perspire?
After being confused by the logo for about a year i finally decided to figure out it’s name. I took it as it was with no functional groups and came up with 1,2-dimethyl-4-(2-methylbutyl)cyclohexane as predicted by Chem Draw, but i agree that it has to be stylized if it was to contain any functional groups.
I thought I’d comment on this article after finding it while conducting research for a logo I’m designing. And should mention I’m a previous bio-analytical chemist, now graphic and digital designer, take a look at my website for more, or google “Creatifik”.
Anyway, I jumped on this article to comment so as to save you guys time, albeit maybe to late by my reading of all the attempts to “chemically” understand the structure.
So let me enlighten you:
!! IT IS JUST A LOGO !!
To understand more I suggest conducting some much needed CPR to your right hemispheres by visiting a gallery with modern art while trying to not be so literal.
What Phillip wrote about maybe its just a techy looking graphic is correct, and there’s absolutely nothing wrong with that.
Ciao,
Stuart