Synth. and Pharm. of Some Hydroxylated Tryptamines

[pHarmacist]

Synthesis and Pharmacology of Some Hydroxylated Tryptamines
Robert G. Taborsky, Peter Delvigs, Djuro Palaic, Merlin Bumpus;
J. Med. Chem.; 1967; 10(3); 403-407.
____ ___ __ _
Full-Text:

http://pharmacist8.tripod.com/OH-trypt.pdf

[Chimimanie]

Nice.

I have also a paper describing the synthesis of 6-OH-5-MeO-DMT from vanillin as well as the much interesting 4-OH-5-MeO-DMT from o-vanillin. This 5-Methoxy-psylocin should bee VERY interesting   . Shulgin has a quote about it in Tihkal#30

http://www.erowid.org/library/books_online/tihkal/tihkal30.shtml

.

Unrelated but semi-related  anyway is that I have another paper which describe the synthesis of 5-MeO-mono-N-alkyl-tryptamine. In tihkal#49

http://www.erowid.org/library/books_online/tihkal/tihkal49.shtml

Shulgin has a word on them. It appear that the tertiary-butyl analogue, NTBT, is a GHB like intoxicant, but the other are likely not active with a straight indole ring. But the 5-MeO-mono-N-alkyl-tryptamines are active according to my ref, with the exception of 5-MeO-NMT, which is Tihkal#42

http://www.erowid.org/library/books_online/tihkal/tihkal42.shtml

and is indeed not active. According to my paper it has an activity of 3-10 in the usual serotonin test, 10 being inactive, but the 5-MeO-NET, which is not in Tihkal, has an activity of 0.1, that is in the same range that DMT/DET etc... It should bee active in the man.

My two papers are
Bull. Soc. Chim. France  (1965), (5),  1411-17 and 1417-1423, from the lab of Mr Julia.

I could not stop thinking of the potential of this 5-MeO-psylocin   .

[Lilienthal]

Sorry, but I don't expect the 5-MeO-4-OH-tryptamines to be psychedelic. The 5-MeO-4-F-tryptamines are binding preferentially to the 5-HT1A receptor (Paper from Nichols' lab). The bonding to the 4-OH is probably from a receptor residue over the indole-5-position, which is blocked by the 5-MeO. Additionally the 4-substituent moves the methyl of the 5-MeO into that direction due to steric interactions.

[Chimimanie]

Mhh, it would be sad  

But anyway, there is a little pharmacological data in the text, the full pharmacology is in another paper I dont have yet. In the rabbit hyperthermia (research of psychotomimetic action) test of the 5-MeO-4-OH, 5-MeO-6-OH and 7-MeO-6-OH tryptamines, they say that only the 4-benzyloxy-5-MeO DMT, 6-OH-5-MeO DMT and 6-OH-5-MeO-DET are active   , all 1 order of magnitude less than 5-MeO-DMT and so the 6-OH is unfavorable (like shulgin say in tihkal). The 4-OH-5-MeO compound is very unstable, and they attribute to that instability its lack of effect.

But they say also that they are not mimetic- (nor anti- BTW) of the serotonin in the rat uterus test.

And that 7-MeO-6-benyloxy DMT has a stimulating action.

As 4-benzyloxy-5-MeO-DMT is at least active in the rabbit, I think the compound should bee researched, and tasted and then we will know. The full pharmacological article should be very useful in a first time too.