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N, N Subbed Tryptamines

blueberries

blueberries

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This may be a stupid question but I've been googling for a while and I keep getting 5,7 DHT. What would be the outcome of N, N Dihydroxytryptamine? I imagine it'd be fairly weak, probably inactive, but what about say N, N Methyl Hydroxy Tryptamine? or DiMethyl-Methoxy Tryptamine, or even just Dimethoxytryptamine itself?

On another note, which I am very doubtful about, what would the result of N, N Difluorotryptamine? I mean halogens are pretty hard to break but maybe that's why it could be inactive? One could always do N, N Methyl-methfluorotryptamine instead to retain at least some hallucinogenic activity.

Finally (this is a little out of the box, I know) but looking at PCP's activity at the 3 position it seems that an amine group produces a similar effect as the methoxy. Diaminotryptamine anyone? Christ even N, N Diamino, N, N, N, N Tetramethyltryptamine!!

Anyway let me know your thoughts.
 
Nitrogen atoms don't like to bond to anything other than hydrogen or carbon. When you put multiple oxygens on it, it's not so happy any more.

N-hydroxycompounds are known as hydroxylamines. N,N-dihydroxy amines are not stable, I don't think, and probably degrade to nitroso (R-N=O) compounds. You could probably form a N-methoxy compound though.

N-fluorinated compounds are not known, I don't think. The analogue with N-chloro compounds is a chloramine, which are usually very reactive and toxic.
 
I'm interested in the methoxy but I think once it's metabolised it wouldn't hold much hope for activity but I'm no scientician. What about the N,N-DiMethyl-Methoxy though? The amine could handle the methyl, the second methyl would be cleaved, leaving DiMeOH. This was the one I put most faith in to be honest. Also the N-fluoro would be Methyl-fluoro not just a straight N-F bond. I suppose you could even make it DiTFM if you really want!

Oh yeah and how about CPM bonds? I'm guessing the potency would be down but MCPMT may work.

black53 said:
http://chemistry.mdma.ch/hiveboard/rhodium/pdf/nichols/nichols-fluoro-meo-pyr-t.pdf
Click to expand...

Hmm, I'm interested in the 6-fluoro-5-methoxy-N,N-dimethyltryptamine. Shame it didn't go into more detail. For that matter, how would a methyl bond work at the 4 position? The methoxy works, albeit poorly, but I reckon it'd be at least a little more potent anyway.
 
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