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