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The hypothetical effects of 2c-m ?

4:20-VERTIGO

Bluelighter
Joined
Jan 6, 2003
Messages
124
You know I was wondering about something. Sence the euphoric effects of MDMA are so popular and the mildly hallucinogenic effects of the 2c series less crash producing,( from what I'v heard ). What would be the out come effects of a drug that contains a methylene link and is based to a Dimethoxyphenethylamine group ?
( Methylene Dimethoxyphenethylamine )
What effects do think it would produce ?
And would it be hypothetically possible to make ?
 
On a sorta-related topic, 2C-MDMA or 3,4-methylenedioxy-N-methylphenethylamine (the phenethylamine "version" of MDMA) has been produced. It has no known central activities, but it is a cough suppressant.
From http://www.erowid.org/library/books_online/pihkal/pihkal115.shtml
"The N-methyl homologue of MDPEA is METHYL-H, and it has been looked at, clinically, as an antitussive agent. N-METHYL-MDPEA, or METHYL-H, or N-methyl-3,4-methylenedioxyphenethylamine is effective in this role at dosages of about 30 milligrams, but I have read nothing that would suggest that there were any central effects. I have tried it at this level and have found a little tightness of the facial muscles, but there was nothing at all in the mental area."
 
Oh there's no question about methylene dioxyphenethylamine being non active.
But why can't Methylene Dimethoxyphenethylamine be active ?
Dosn't a second link in the compound activate it ?, It being a Di"meth"oxy and not just a Dioxy.
[ 24 February 2003: Message edited by: 4:20-VERTIGO ]
 
i'm just gonna throw out some knowledge and hope soembody can wrap it up into a good answer.
at least a few (hell, maybe even all) of the 2C-x (and DOx) compounds are pro-drugs (or pre-drugs), meaning they are inactive until metabolized.
this is the reason for the long onset of DOx; if you wish to prove to yourself that 2C-x are the same, take some harmala, or any other reversable MAOI, prior to ingesting your 2C-x and watch how long it takes to come on; the alpha methyl group makes the chemical harder to metabolize, and this is why DOx is so much more potent than 2C-x, and also why amphetamine is active, yet phenethylamine is not.
also, the positions on the benzene ring have something to do with the activity. 2,5 and 2,6 dimethoxy 4-substituted compounds are active and very potent, while 3,5-dimethoxy 4-substituted are much less so (count mescaline and TMA in this group, even tho its another methoxy group in the 4 position).
mdma is not a pre-drug. we'll assume this is because of the position of the md-ring on the benzene ring.
i dont know where to go from there... but you CANT predict how a drug will be simply looking at structure.
a phenethylamine version of dmmda, but being methylenedimethoxy instead of methylenedioxy is what you're suggesting?
i dunno if you can do a methylenedimethoxy ring, but looking at G-3 and 2C-G3, it really makes you wonder what it might be like.
 
Hmm, actually this conversation has started me thinking a little bit. I'm wondering if anyone has had the opportunity to try both TMA-2 and MMDA-2? I'm actually curious to see what the differences are in the experiences with these two compounds, since the only difference between them is that one has a methylenedioxy bridge where the other has two methoxy groups. But otherwise all the substituents are at exactly the same positions. Hmm, might have to try and dig up some articles about these two.
Also, now that I start thinking about it, if anyone has had experience with any of these pairs I'd really like to hear some comparisons on them:
3,4-DMA and MDA
Any of the DMMDA's and Tetramethoxyamphetamine
I know that all these are probably stabs in the dark, but still I'd love to hear some first hand accounts.
 
Originally posted by tathra:
i'm just gonna throw out some knowledge and hope soembody can wrap it up into a good answer.
at least a few (hell, maybe even all) of the 2C-x (and DOx) compounds are pro-drugs (or pre-drugs), meaning they are inactive until metabolized.

In all my exploration of the scientific literature, I have NEVER come across this statement in reference to DOI (AFAIK from a search of pubmed, the metabolism of the 2C-X drugs has never been studied except in terms of urinalysis). References please?
Also, catabolism of the drug isn't the only thing that determines how long it takes to kick in. Another important factor is the intra and intercellular signaling that is stimulated by the drug. DOI produces a more generalized pattern of cortical activation than psilocybin or LSD, so it is possible that it may also be activating some type of inhibitory input that takes a while to overcome. Having that alpha-methyl means that DOX binds to the 5-HT2A receptor in a slightly different configuration than 2C-X, so that it differentially stimulates the various signaling cascades that are activated by 5-HT2A agonism.
 
mnmguy - i hadnt really thought that out too well i guess. i personally have only dealt with 2C-B, and had no problems with the 2C-B+harmala experiment. i'm sure the 2C-Tx series wouldnt behave anywhere near the same, nor would the 2C-Gx series... 2cb, 2ci, and 2cc should all be similar in almost every way, though.
5ht2 - i dont have any medical references, just strong implications, as seen in the DOB entry of PiHKAL:
As with DOI, the presence of a heavy atom, the bromine atom, in DOB makes the radioactive isotope labelled material a powerful research tool. Studies with DOB labelled with either 82Br or 77Br have been used in human subjects to follow the distribution of the drug. The use of a whole body scanner permits the imaging of the intact body, with the travelings of the radioactivity easily followed from outside. A fascinating finding is that DOB goes first and foremost to the human lung where it accumulates for a couple of hours. It is only afterwards that the brain level builds up. There is a strong implication that some metabolic conversion occurs in the lung, and it is only after this that the truly active metabolite is available for central action. This is consistent with the relatively slow onset of effect, and the very long duration of action.
i need to study more neurology :)
but at least i accomplished my main goal: stirring up intelligent discussion. also, having your errors corrected is a great way to learn stuff :)
 
The question has just been posted on "Ask Shulgin"... Whether its answered is a different question. I might just e-mail him directly.
Cheers,
:)
 
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