Question about 3C-x

[MrPorter]

I'm also lost on the 'simplified' naming of these compounds past IUPAC, but can at least help you out on one thing...

"phenethylamines/amphetamines"
well a phenethylamine is a benzene ring attached to ethylamine (ch3ch2nh2).
Amphetamine is a phenethylamine which has a methyl group on the alpha carbon (First carbon next to the amine). This gives it the name A(lpha)M(ethyl)Ph(en)ET(hyl)AMINE - AMPHETAMINE.

The alpha methyl ethylamine could also be considered as a 2-aminopropyl group if you think about it...

 

[Dresden]

3,4,5-trichlorophenylethylamine is a stimulant but not a hallucinogen, according to the literature. Not sure about the 3C version.

 

[Solipsis]

That's the problem we saw with the beta-ketones that were oh-so popular. Methcathinone, mephedrone, methedrone, pentedrone, flephedrone, buphedrone, etc. It got a little ridiculous. The appearance and use of the name methedrone was most troubling and retarded. It made and continues to make me wonder if it was name in an intentionally confusing way. While we may all understand the difference here, there are almost certainly people who would mistake it for a typo or just misread it.

Reminds me of some epic post from a BL-er about how Daffy Duck would pronounce flephedrone... which is without a doubt the #1 silliest drug name I know of. Ondansetron is also a nice contestor, but not so much silly as it is cool.

I do agree with Solipsis, no one using these compounds should be confusing the two.

It's interesting that 3C-B isn't known, but 3C-B-FLY is available for purchase already.

Actually thanks for pointing out this huge fail: 3C-B-Fly, or DOB-Fly or B-Fly is the tricyclic version of DOB, not that of 4-br-3,5-dimethoxyamphetamine. Not sure who named this one but it seems like we have come full circle and this is making my point that if for example DOB and "3C-B" are confused, the inconsistent nomenclature of 3C-B-Fly is something that can happen. The fly, dragonfly, hemifly and butterfly (sp? custom named) seem internally consistent in naming but if the groundwork is shaky what do you expect?

3,4,5-trichlorophenylethylamine is a stimulant but not a hallucinogen, according to the literature. Not sure about the 3C version.

Thanks for that idea, but it made me think something like 'you lost me at halogenated amphetamine'. Regarding fears of neurotoxicity that sounds like it may be too harsh from this thread http://www.bluelight.ru/vb/threads/447184-3-4-5-trichloroamphetamine-hcl
but to stay on the safe side, I wouldn't take it. What to expect of it? Something happy like the side-effects of DOX without the psychedelia? Again: who knows if this is too precautious...

 

[sekio]

the only reason the trichloro cmpds are suggested "psychedelics" is because Cl makes an OK OMe bioisostere in some cases.

obviously not in the case of 245 trimethoxy pea...

 

[Draind]

was just in pihkal and somethning i read should be known by all 2cx 3cx peoples,
"A brief reiteration of the 2C-3C nomenclature, to avoid a possible misunderstanding. The drug 2C-B is so named in that it is the two-carbon chain analogue of the three-carbon chain compound DOB. The drug 3C-B is so named because it is the three-carbon chain analogue of the two-carbon chain compound Buscaline, or more simply, B. There is no logical connection whatsoever, either structural or pharmacological, between 2C-B and 3C-B. "

had read something along those lines but now it makes sence. the 2c/3c shouldnt have too much of a connection ie: 2c-b/3c-b.

 

[Solipsis]

the only reason the trichloro cmpds are suggested "psychedelics" is because Cl makes an OK OMe bioisostere in some cases.

obviously not in the case of 245 trimethoxy pea...

Yeah and I still don't really understand why 2C-O is inactive... might it be possible that this has something to do with the fact that mescaline is not just a typical 5-HT agonist? Because I'd expect that if you hybridize structures of compounds that are categorically in the same pharmacodynamic group, this tends to work because if compound A employs a certain pharmacophore and compound B employs the same one then logically the hybrid should be a fair match.
Yet, if we try to hybridize drugs that are categorically different, like a monoamine releaser and a typical psychedelic... there are multiple pharmacophores involved and therefore a hybrid of 2 completely different analogues can easily fall outside of category A as well as B.

Hmm IDK maybe the reason for 2C-O is entirely separate like MAO-B eating it (probably not) or who knows.

was just in pihkal and somethning i read should be known by all 2cx 3cx peoples,
"A brief reiteration of the 2C-3C nomenclature, to avoid a possible misunderstanding. The drug 2C-B is so named in that it is the two-carbon chain analogue of the three-carbon chain compound DOB. The drug 3C-B is so named because it is the three-carbon chain analogue of the two-carbon chain compound Buscaline, or more simply, B. There is no logical connection whatsoever, either structural or pharmacological, between 2C-B and 3C-B. "

had read something along those lines but now it makes sence. the 2c/3c shouldnt have too much of a connection ie: 2c-b/3c-b.

Wow excellent resolution, thanks.

So it's like I suspected all along (check post #9): one should be careful because the letters can mean other things and B is taken for buscaline like "E" and "P" are taken for escaline and proscaline (not ethyl and propyl). Meaning that if you desperately want a name for 4-chloro-3,5-dimethoxyamphetamine it should probably 3C-CM all along assuming the code CM is not yet taken. Because unlike "C", "CM" could designate chloromescaline / chloroscaline.

 

[sekio]

Apparently 2C-O *is* active (at least IV, I guess... see PiHKAL TMPEA / 2C-O), but not as potent nor as desirable as mescaline.

(with less than 300 mg) Since it was not easy, however, to judge the extent of a 'Rausch'-action from experiments on animals, some injections of beta-2,4,5-trimethoxyphenethylamine were administered to the author, and finally a control test was carried out with an equal quantity of mescaline. The action of both these substances in these experiments agreed only to a limited extent with the effects described for mescaline by, for example, Beringer. It must be remembered, however, in this connection, that the quantities used by Beringer were larger than the doses administered in these experiments. Nevertheless, it may be concluded that the pharmacological action of beta-2,4,5-trimethoxyphenethylamine agrees to a large extent with that of mescaline. However, the new compound had more unpleasant secondary effects (nausea) and did not bring about the euphoristic state caused by mescaline.

I iamgine if you took a half-gram orally you would see effects. But, nobody wants to do that.

 

[Incunabula]

Yeah and I still don't really understand why 2C-O is inactive... might it be possible that this has something to do with the fact that mescaline is not just a typical 5-HT agonist? Because I'd expect that if you hybridize structures of compounds that are categorically in the same pharmacodynamic group, this tends to work because if compound A employs a certain pharmacophore and compound B employs the same one then logically the hybrid should be a fair match.
Yet, if we try to hybridize drugs that are categorically different, like a monoamine releaser and a typical psychedelic... there are multiple pharmacophores involved and therefore a hybrid of 2 completely different analogues can easily fall outside of category A as well as B.

Hmm IDK maybe the reason for 2C-O is entirely separate like MAO-B eating it (probably not) or who knows.





Wow excellent resolution, thanks.

So it's like I suspected all along (check post #9): one should be careful because the letters can mean other things and B is taken for buscaline like "E" and "P" are taken for escaline and proscaline (not ethyl and propyl). Meaning that if you desperately want a name for 4-chloro-3,5-dimethoxyamphetamine it should probably 3C-CM all along assuming the code CM is not yet taken. Because unlike "C", "CM" could designate chloromescaline / chloroscaline.

I absolutely agree. I'm actually begining to think that the 3C-nomenclature shouldn't be used at all for new compounds. And that it should only be used for the ones Shulgin already named so.

it's too confusing. And leads to too many missunderstandings, like with 3CB-FLY.

 

[Jakeperson]

^^+1

 

[pharmakos]

I absolutely agree. I'm actually begining to think that the 3C-nomenclature shouldn't be used at all for new compounds. And that it should only be used for the ones Shulgin already named so.

it'd be really easy for the press/legislature to attach the 3C's to the already illegal 2C's if they were named as such.