O-Methylnordehydrobufotenine is hallucinogenic?

[Nicodem]

This old paper claims a hallucinogenic effect from a ring fused derivative of 5-MeO-DMT (the ethylamine side is fused at the indolic position 4 trough N). It seams quite unlikely to that such compounds would be “tryptaminic”. Maybe the results of the behavioral effects on mice were misinterpreted. Anyway, I posted it in case somebee wants to comment on it:


The Synthesis of O-Methylnordehydrobufotenine, a New Psychoactive Indole.
Fred G. H. Lee, John W. Daly, and Albert A. Manian
J. Med. Chem. 12 (1969) 321-322.

Excerpts: Because of the high CNS activity shown by N,N-dimethyl-5-methoxy-tryptamine, the synthesis of the structurally related tricyclic indole, O-methylnordehydrobufotenine (6-methoxy-5-methyl-l,3,4,5-tetrahydropyrrolo [4,3,2-d,e]-quinoline), was undertaken.
…
In this test, the O-methylnordehydrobufotenine (He) is approximately twice as active as mescaline (ED₅₀ = 71.0 umoles/kg), but is much less active than its open-chain analog,  N,N-dimethyl-5-methoxytryptamine, which from published data can be estimated to be much more than 30 times as active a hallucinogen as mescaline. When injected subcutaneously into NIH general purpose white mice, O-methylnordehydrobufotenine at 20 mg/kg causes only slight overt changes (reduction in spontaneous activity) while N,N-dimethyl-5-methoxy-tryptamine at 10 mg/kg causes profound effects. At this dosage the mice lose the ability to move normally and engage in locomotor activity with legs extended laterally.


Shulgin says this about O-Methylnordehydrobufotenine: »This is a rearrangement product of dehydrobuftenine, which may be a natural product or it may be an artifact of analysis.«

http://www.lycaeum.org/books/tihkal/19--5-ho-dmt.shtml

And also seamingly cites the results of the above paper when he says: »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-methylnordehydrobufotenine, proved to be of comparable activity to DMT in rat studies, but has not apparently been studied in man.«

http://www.lycaeum.org/books/tihkal/42--5-meo-nmt.shtml

[Fastandbulbous]

Nicodem
I was just looking thru some old note I made when at university, and I came accross something that reminded me of this post.
The compound (structure below) was stated to be active as an hallucinogen (sorry no refs, and no other data about it).
The only reason I made a note of it is because, at the time, I thought it had a strange structure for a psychedelic. I now see it is like a cyclicised alphamethyltryptamine. Will post if I find any more info in my notes.

[ning]

Not to mention bearing a very suspicious resemblance to LSD...