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New subs on the psychedelic amphetamines

T

toxide

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Mar 21, 2006
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Can some tell me whether or not the psychedelic amphetamines can have simple alkyl or halogen substitutions at the 2,5,6 positions instead of alkoxy and alkylthio. For instance something like 2,5-Dibromo-4-Chloro-A or 2,5-Dimethyl-4-Chloro-A or even weirder 4-tert-Butyl-3,5-DiNitro-2,6-DiMethyl-A. I ask because that last one is available (as are the 1st two), but it seems real odd, not sure I'd ever try it anytime soon but I was curious if anyone could speculate on the activity of these differently substituted amphetamines.
 
Probably no psychedelic activity on those. The 5ht receptor needs those methoxy groups to form hydrogen bonds.

edit: the dinitro compound seems really sketchy. I wouldn't eat it.
 
DMT doesn't seem to have a problem serving as a 5-HT2a agonist.
 
Who said that tryptamines and amphetamines have to same binding mode?

Dread was right, the methoxys are necessary for hydrogen bonding and thus viable activity.

- Murphy
 
I thought he meant of any drug, but later I realized he probably meant psychedelic amphetamines.

Anyway, I think it is safe to say that the OP would be risking his own life if he were to try any of those molecules on himself with so little information other than their structures available atm.
 
You could put a halo or alkyl at the 6 position, keeping dimethoxys at 2 & 5 and still have activity. Believe Shulgin did this with DOM, called it ψDOM IIRC. Speculated that all DOx would have a similar homologue, dunno if any more were synthed or tried. Also I believe the dose had to be upped substantially & the duration was shortened quite a bit as well. Which could definitely be a good thing with DOx
 
Psi-DOM has a 4-methyl and one methoxy at 2 and another methoxy at 6.

Also, 2,5,6 should be called 2,3,6.
 
I think I remember something in the Hive about 3,4,5-TrimethylPEA making cat's bugout but I think cat's neurochemistry is somehow very different than most other mammals so that probly doesn't mean anything. I always just blindly assumed that the methoxies on the PEAs where like the MEOs on tryptamines(like 5-meo etc...) and 5-methyl-DMT is known, just alittle less potent. But the 2 families really are way different. So why is a Sulphor atom able to replace an oxygen on the alkyl?
 
(zonk) said:
I think I remember something in the Hive about 3,4,5-TrimethylPEA making cat's bugout but I think cat's neurochemistry is somehow very different than most other mammals so that probly doesn't mean anything. I always just blindly assumed that the methoxies on the PEAs where like the MEOs on tryptamines(like 5-meo etc...) and 5-methyl-DMT is known, just alittle less potent. But the 2 families really are way different. So why is a Sulphor atom able to replace an oxygen on the alkyl?
Click to expand...

compare the structure of DOM to LSD and 5MeO-DMT. Hint: the Nitrogen of the indole nucleus corresponds to the 5-MeO of DOM, and the 5-MeO from DMT is in the same general location as the 2-MeO of DOM. i don't understand why Shulgin never tried alkylating the 7-position of tryptamines, as it appears analogous to the 4-position of the Pihkals.

sulfur lies directly below oxygen on the periodic table, and behaves similarly in many cases (hydrogen bonding, electronegativity), it's just a little heavier and very stinky.
 
There's no 5-methoxy on DMT. There is on 5-Meo-DMT, but DMT is active without it.

You're making the mistake that someone who hasn't read much about 5HT2a binding would make. Tryptamines and Phenethylamines do not bind the same way. When it comes to 5HT2a binding, it's a mistake to look for homologous positions, because they're not interacting with the receptor in the same way.

I believe there are some SCAM studies that shed light on the different AA interactions of tryptamines and PEA's.
 
ok then, does LSD bind in the PEA mode or the trypt mode? both skeletons can be traced in its structure, but which one is responsible for its activity?

if it is the PEA mode, then why does extending the N-alkyl chain (ETH-LAD) increase potency? (usually kills psychedelic activity on PEAs)
if it is the trypt mode, then how is it so potent without the 5-MeO?
 
maybe if there is 5-meo type position yet to be found on the lysergamide it may increase potency, who said there wasnt. I can assure you it's not the PEA as LSA<LSD, AMT is the only one that I know that kinda is it's own thing as any subs at the 1/N seem to diminsh the trippiness
 
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