N,N`,3-trimethyl-5-hydroxytryptamine does NOT exist.
But 1,3-dimethyl-3-(2-methylaminoethyl)-2,3-dihydro-1H-indol-5-ol does.
And Cooper don`t see any difference!?!
I searched Medline for the Brossi`s article and found the following:
Further explorations on unnatural alkaloids
Bossi A.
J Nat Prod 1985 Nov-Dec 48:878-93 Medline (PMID=86142792)
accompanied with the abstract below:
(+/-)-N1-noreseroline-O-methyl-ether, prepared by a modification of the Julian total synthesis, afforded with R-(+)-methylbenzyl-isocyanate two diasteromeric ureas, converted individually into (+)- and(-)-eseroline after thermolysis, N-methylation and O-demethylation. (+)-Physostygmine was obtained after reaction of (+)-eseroline with methylisocyanate. Biological properties of (-)- and(+)-eseroline and (+)-physostigmine will be reported... continuing with info about colchicine and MPTP research What I know about physostigmine is that it`s an agonist of muscarine and respectively - antagonist of atropine. And then I found the information below:
Physostigmine (eserine),C
15 H
21 N
3 O
2 , MW 275.3, CAS 57-47-6, MI 13: 7469, crystaline solid, soluble in chloroform, toxic - forms a carbamylated enzyme complex with acethylcholinesterase that degrades slowly. Crosses blood-brain barrier.
(-)-Eseroline.fumarate, C
13 H
18 N
2 O.C
4 H
4 O
4 , MW 218.3 . 116.1, CAS 104015-29-4, white solid, soluble in water or DMSO, slightly soluble in MeOH, metabolite of physostigmine (eserine), potent analgesic.
References:
Medline (PMID=6293841)
Medline (PMID=7092918)
Medline (PMID=2858526)
So...the analgesic "tryptamine" is actually eseroline. The price of (-)-eseroline fumarate is around 50euro/10mg or 170 euro/50mg and the price of physostigmine is 25euro/100mg (bioresearch grade). Hmm...interesting.