• N&PD Moderators: Skorpio | thegreenhand

  • Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

benzoxazole analogs of MDMA

I wish I'd had a chance to try IAP + amphetamine. I tried IAP alone and with BDB - both times they were utterly useless. Almost dysphoric in a way. But I could tell the whole time that if I added some dopaminergic stimulant to it to make it euphoric, the synergy would be very much like MDA.
 
nuke said:
Couldn't this be dangerous if it metabolises into an o-formamido phenpropylamine in vivo (eg carcinogenic)?
Click to expand...
if it did then it would possibly be carcinogenic, I don't think it will, there are several benzooxazole drugs out there and I don't think that metabolism opens the ring with these. benzooxazole appears a rather stable moetry.
 
I don't have the paper anymore but nichols did investigate the dihydrofuran analog of MDMA I think it was the isomer with the 4 position oxygen replaced with 'Carbob' which fully substituted for the training drug. am i correct in thinking the 4 position o seems less critical for DAT SERT selectivity than the 3 o? If that is the case then that is where the N should go.
Click to expand...

Yeah, I've read & re-read it and the one wit the oxygen in te 4 position is less entactogenic than IAP due to poorer DAT (andNET) activity, the one with the oxygen on the 3 position was far better than IAP and not far behind MDA in DAT & NET activity and looks like it could be a real winner (many moons ago, in TR I posted the results of a bioassay of the 4-O compound - 5-(2-aminopropyl)-2,3-dihydrobenzofuran - and while enjoyab;le was nowt like MDA. unfortunately the 3-oxygen compound - 6-(2-aminopropyl)-2,3-dihydrobenzofuran is a lot harder to synth. Que ser sera)

IAP and MDPV!
Click to expand...

Yeah, that would do the trick!
 
nuke said:
Couldn't this be dangerous if it metabolises into an o-formamido phenpropylamine in vivo (eg carcinogenic)?
Click to expand...

contrary to what I said earlier , in the rabbit benzoxazole metabolises through ring rupture to give acetyl derivatives of the o amino phenol as well as free acetamino phenol and its gluconorides. o amino phenol is a suspected, though not very effective, human carcinogen, associated with bladder cancer.
 
Yes but cleavage of the ring doesn't give ortho aminophenol, ir gives 4-amino-3-hydroxyamphetamine and the reason most carcinogens like that are so dodgy is that the body resorts to desparate metabolic measures to make the substance polar to facilitate excretion. The 2-aminopropyl contains a polar non aromatic amine group that can give the body (well kidneys) the handle with which to remove it from the bloodtream. it's analogous to the relationship between benzrne and amphetamine, yet amphetamine doesn't cause bladder cancer as it's not formed into the epoxide metabolite the way benzene is. similarly, aromatic amines are well didgy, but para-aminobenzoic acid it totally safe because of the polarity of the carboxylate group
 
fastandbulbous said:
similarly, aromatic amines are well didgy, but para-aminobenzoic acid it totally safe because of the polarity of the carboxylate group
Click to expand...

but what about o-formidophenol, the main metabolite in rabbits?
 
nuke said:
but what about o-formidophenol, the main metabolite in rabbits?
Click to expand...


What actual Oformimidophenol or a formamidophenil with a 2-aminopropyk chain attached to the aromatic nucleus. If it's the latter then it'll get pissed out reasonably quickly along witnother metabolites due to the polar sidechain group

IMAP + MDPV here we come...
Click to expand...

Is the first one N-methyl IAP? if so a friend who synthed it came up with a better acronym, namely IMP (IndanylMethylaminoPropane). I think Shulgin, with his sense of humpour, would approve!
 
So have there ever been any compounds made with a secondary amine (amino ether?) @ the 3 position? or 4 for that matter?
Just out of curiosity, and delete if inappropriate, starting with the benzoxazole, NBS->allylic or aldehyde-> topic of interest? or would the all that pi-system bee too difficult for selective halogenation?
 
Would the fully aromatic equivalent of Indanylaminopropane be possible?

Also the idanyl versions of the fly compounds would be interesting if they were possible too.
 

Attachments

  • untitled.gif
    untitled.gif
    3.1 KB · Views: 107
Reminisant B said:
Would the fully aromatic equivalent of Indanylaminopropane be possible?

Also the idanyl versions of the fly compounds would be interesting if they were possible too.
Click to expand...

yes the indene group is known and stable, most routes to IAP and IMP start with indene, and convert it to indan and stick the isopropylamine tail on.

dont see much point in indanyl versons of the dragonflies, the almost certainly will be inactive as hallucinogens
 
But not a fully aromatic version of IAP - you need to have a series of conjugated double bonds for aromaticity or a heteroatom that can donate a lone pair to the pi electrons
 
After reading about the neurotoxicity of placing amines on the ring position of phenethylamine and amphetamine, I'm going to put a big warning on these compounds -- some of the rat studies of these o-aminergic compounds are horrific (monoamine depletion worse than methamphetamine and with different specificities).
 
You must log in or register to reply here.
Top