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What is the saturation of the methylene group on MDMA?
Q: Please forgive me if I'm asking a stupid question - I am, after all, but a humble amateur - but I was looking through your ChemVault on 3,4-methylenedioxy N-methyl alpha-methyl beta-phenyl ethylamine (MDMA), and I noticed that you display the methylenedioxy attached as being fully hydrosaturated. By my limited studies in organic chemistry, the -ane suffix, as in cyclohexane, is used for fully-hydrosaturated carbon compounds, whereas the -ene, as in benzene, is used for those which are not fully saturated - usually containing double or triple bonds, as with benzene, propylene, and the like, though this is naturally rather difficult with methylene.

So naturally, I'm just a bit lost as to whether it's a-, mono-, or di-saturated by hydrogen. If you would be ever so kind to help clear up my struggle for knowledge, I would be ever so greatful.

-Psi Locybe, mad alchemist.

A: You have the general idea right. The -ane, -ene, -ine suffixes typically refer to whether or not the bonds involved are a single, double, or triple bond and thus the saturation/orbital hybridization. However, a CH2 group, which will have two single bonds going to/from it in addition to those two hydrogens, can be called a "methylene carbon". It is fully saturated, and does not contain the hybrid orbitals of a double bond, but that is the correct nomenclature. Similarly, a CH within a molecule could be called a "methine carbon". So in these cases, you have the nomenclature referring more to number of carbons bound than the state of the bonds.



Asked By : Psi Locybe
Answered By : psilo
Published Date : 7 / 27 / 2001
Last Edited Date : 7 / 27 / 2001
Question ID : 2760

Categories: [ Chemistry ] [ MDMA (Ecstasy) ]

Ask Erowid v1.7 - Jul, 2005

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