2c-c / DOC question for you, chemical experts!

[last.baron]

From the wikipedia entry on DOC

"DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C"

Ok so, as I got it, the only thing differentiating DOC and 2c-c is this alpha-methyl group, that is missing in the latter.
Now, what this actually means? Chemically speaking!
This is not a "what's the difference this thing has on me" or "can i take doc, remove alpha-methyl group with some funky device and get 2c-c" question: it's just pure and sheer curiosity, out of ignorance :D
I know it sounds like a lame question, and probably it doesn't even fit in this section of the forum, but still I'm very curious, and I can't sleep
Hit me with whatever you have, any little bits of information is usefull! What are the property of this alpha-methyl group? Is it present in other compounds? Does it "twists" other compunds? Anything really
Thank you!

 

[jhoppa]

An alpha-methyl group turns a phenethylamine into an amphetamine; that's actually where the word comes from. alpha-methyl phenethylamine. Is that what you mean?

All of the 2C compounds have a DOx amphetamine counterpart. The 2C part of their name is in reference to this: when you remove the alpha-methyl from a DOx, you turn a three carbon chain into a two carbon (2C) chain.

 

[last.baron]

I wasn't looking for a particular answer, just informations, like yours
Very usefull! I'm just trying to expand my grasp on the easy and basic concept: I don't want to develope stuff or anything, I don't have the skills to, but I really like to be informed on the things I like and use!
Thank you very much!
if you know other "class" of compounds that behave like that, or that are just similar in concept (adding groups to substances to make it other substances, and how those substances are related one to another), feel free to share!

 

[Deinonychus]

Okay. Take a look at 2C-C.

2C-C

Now take a look at DOC.

DOC

The nitrogen is a primary amine, meaning two of its three bonds are occupied by hydrogen atoms. This nitrogen is referred to as being the N position. Working your way down the chain, from the N position to the benzene ring, you move through the greek letters. As you can see, the carbon that is closest to the nitrogen, the alpha, has no functional groups attached to It in the case of 2C-C. In DOC, there is a methyl group (carbon with three hydrogens), attached at the alpha position.

To further illustrate my point about the Greek alphabet naming convention, examine amphetamine and cathinone.

Cathinone is simply amphetamine with an oxygen double bonded to the next carbon down the chain, the beta. We refer to an oxygen double bonded to a carbon as a ketone, hence cathinone is thus bk-amphetamine (bk for beta-ketone).

Making sense?

 

[donvliet]

All of the 2C compounds have a DOx amphetamine counterpart. The 2C part of their name is in reference to this: when you remove the alpha-methyl from a DOx, you turn a three carbon chain into a two carbon (2C) chain.

So if I understand correctly, the following pairs are related in this way:
DOC > 2C-C
DOB > 2C-B
DOI > 2C-I
What about 2C-E, 2C-P, 2C-D etc? And DOM?

 

[jhoppa]

2C-E's counterpart is DOET, 2C-D has DOM, 2C-P has DOPR.

The naming gets a bit esoteric, but the chemical structures match up.

 

[sekio]

Go read PiHKAL for more information, Shulgin has covered the bases w.r.t the 2c- and dox compounds

 

[Solipsis]

Mescaline, escaline, proscaline and allylescaline are also 2-carbon PEA's like the 2C's, however their associated amphetamines are not called DOX, but:
TMA, 3C-E, 3C-P and 3C-AL.

It could help for you to take a big piece of paper and draw the structures of these drugs together with their names. Then compare those structural formulae as they're called, spot the differences.

The alpha-methyl thing means: there is a place on the molecule of 2C compounds and also other 2-carbon phenethylamines, that place is one of the carbons of the chain which is called the alpha-carbon (Cα). The other one is called the beta-carbon. They are just being counted (alpha = 1st, beta = second letter of greek alphabet) starting at the amine (N / NH2).

The Rα (R stands for radical or rest group, it's like the X in 2C-X), is where a group can fit on that alpha carbon. A methyl group put there makes the phenethylamine an amphetamine.