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  • N&PD Moderators: Skorpio | someguyontheinternet

5-substituted tryptamines

Dondante said:
From another thread:



I'm intrigued by the possibility of psychedelic activity from cyclization products of simple tryptamines. In TIHKAL, O-methyl-nordehydrobufotenine is mentioned under the entry for 5-MEO-NMT. This mention is made in the hard copy only, which adds even more mystery to the question!

Shulgin writes, "A fascinating cyclization product of this "nor-compound" is a cyclic dehydrogenation product where there is a direct coupling of the tryptamine nitrogen to the 4-position of the indole ring. This tricyclic material, O-methyl-nordehydrobufotenine, proved to be of comparable activity to DMT in rat studies, but has not apparently been studied in man."

I've always thought that tryptamines folded up kinda like this anyway, internal salt interaction though, rather than covalent bond.

I attached the structure of dehydrobufotenine.
Click to expand...

I don't think the structure shown is correct. I can't see the N,N-Dimethylaminotryptamine cyclizing to a quaternary amine. Second, the structure as shown, being a quaternary amine, would probably not be active - way too polar to cross the lipid barrier.

See page 563 of the following for a simple alternate synthesis and the correct structure.

http://www.iupac.org/publications/pac/1997/pdf/6903x0559.pdf
 
O-methyl-dehydrobufotenine looks an awful like the sertonin antagonists mentioned below that one (page 6 right?) the 1,2,3,4,5 tetrahydrobenz(cd)indoles, if you ask me.
 
Hey retired chemist, im wasnt talking about DET HCl, the freebase i had was a white solid. I dont think tastes like shit quite does it justice! It not only tastes like shit but engulfs you from the inside out with its shittyness, like drowning in shit.
 
hehe, is that why youre interested in tryptamines? want to find the substitution pattern that gives the best stench!
 
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