Am I correct to say that N,N-diethyl-meta-toluamide (DEET) is a part of the phenethylamine class? It's structure meets the requirements to be a phenythylamine, however, I was not able to find anywhere on the internet that it is part of the phenethylamine class.
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$\begingroup$ Do you mean phenethylamine? That's the only thing google turn's up. If so, they don't seem to be related (1 less carbon between ring and N, carboxylic-bound N versus amine N) $\endgroup$– NicolaiJun 28, 2017 at 8:32
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$\begingroup$ @Nicolai Sorry I usually type in Word which autocorrects me, but you are correct on the first part. But I'm confused on your second point. How come it passes the requirements to be a substituted phenethylamine (en.wikipedia.org/wiki/Substituted_phenethylamine)? $\endgroup$– kirill2485Jun 28, 2017 at 9:03
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$\begingroup$ Selegiline is a good example of what I mean, it has a carbon bound N but is part of the PEA class. Why is this then... $\endgroup$– kirill2485Jun 28, 2017 at 9:04
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$\begingroup$ Also, technically DEET has a NH group because groups share atoms with the linked group, so writing N-CH3 is the same as writing NH-CH2. There is no difference, unless it crosses over 1 link. $\endgroup$– kirill2485Jun 28, 2017 at 9:07
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3$\begingroup$ I'm voting to close this question as off-topic because it is not about biology, but is a question about the chemical structure of a proprietary product. $\endgroup$– DavidJun 28, 2017 at 17:10
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1 Answer
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While I feel like this might be a better question for the chemistry SE, lets take a look at the molecular structures:
The basic structure of a phenethylamine (left, modified from here) versus DEET (right, modified from here):
The important chemical differences are:
- DEET only has a C-alpha between the nitrogen and the ring, whereas phenethylamines have a C-alpha and a C-beta (see red annotation)
- DEET has a carboxylic functional group (an amide bond), whereas phenethylamines have an amino group (see green boxes)
Taken together these differences mean that DEET is not a phenethylamine.
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$\begingroup$ So are you saying that 1-phenethylamine is not part of the phenethylamine class? $\endgroup$ Jun 28, 2017 at 12:47
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$\begingroup$ Note, I am not talking about b-phenethylamine which is the one you pointed out $\endgroup$ Jun 28, 2017 at 12:50
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$\begingroup$ @kirill2485 At least based on the different carbon chains of these molecules I wouldn't group them together. I'm not a chemist however, so if you want to now how they categorise this, ask the question at chemistry.SE $\endgroup$– NicolaiJun 28, 2017 at 14:09
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1$\begingroup$ I agree with @Nicolai I can't see any reason it would make sense to consider DEET a phenethylamine; it doesn't have an "ethylamine" on it anywhere: that would be 2 carbons followed by a nitrogen. It's an N-substituted amide group (one carbon) on a toluene. $\endgroup$– Bryan Krause ♦Jun 28, 2017 at 18:05