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O-Methylnordehydrobufotenine

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O-Methylnordehydrobufotenine
Clinical data
Other namesO-Methyldehydrobufotenidine; 6-Methoxy-5-methyl-1,2,3,4,5-tetrahydropyrrolo[4,3,2-d,e]-quinoline
ATC code
  • None
Identifiers
  • 9-methoxy-7-methyl-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(12),3,8,10-tetraene
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H14N2O
Molar mass202.257 g·mol−1
3D model (JSmol)
  • CN1CCC2=CNC3=C2C1=C(C=C3)OC
  • InChI=1S/C12H14N2O/c1-14-6-5-8-7-13-9-3-4-10(15-2)12(14)11(8)9/h3-4,7,13H,5-6H2,1-2H3
  • Key:PRPCWBYVLURNKE-UHFFFAOYSA-N

O-Methylnordehydrobufotenine, also known as O-methyldehydrobufotenidine or as 6-methoxy-5-methyl-1,2,3,4,5-tetrahydropyrrolo[4,3,2-d,e]-quinoline, is a tricyclic cyclized tryptamine and analogue of 5-MeO-DMT and bufotenine.[1][2][3][4] It produces hallucinogen-like effects in monkeys and rodents.[1][3][4] However, although more potent than mescaline, O-methylnordehydrobufotenine was far less active than its open-chain analogue 5-MeO-DMT.[4] The drug is not known to have been tested in humans.[3] O-Methylnordehydrobufotenine was first described in the scientific literature by 1969.[1][3][4]

See also

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References

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  1. ^ a b c Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. p. 10. OCLC 1194694085. In addition, Lee, et al,(31) have prepared O-methyl nordehydrobufotenin 6 and found it to be active. Although it does not satisfy correlate 1 of Chothia and Pauling, it has the required aromatic system and point of electron density at the 4 indole position.
  2. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "O-Methylnordehydrobufotenine: This is a rearrangement product of Dehydrobufotenine, which may be a natural product or it may be an artifact of analysis."
  3. ^ a b c d Trout K (2007). "O-Methyl-nordehydrobufotenine: 6-Methoxy-5-methyl-1,2,3,4,5-tetrahydropyrrolo[4,3,2-d,e]-quinoline.". Some Simple Tryptamines: A Brief Overview & Resource Compendium FS-X7. Activity: Hallucinogenic in animals. # 409 in Usdin & Efron 1979; citing Lee et al. 1969. Despite not actually ever being proven to be a hallucinogen in either animals or humans, this is interesting as, while it remains unreported as a naturally occurring alkaloid, this molecule is a simple rearrangement product of dehydrobufotenine. It suggests that it too may be physiologically active albeit possibly moderately toxic.
  4. ^ a b c d Lee FG, Daly JW, Manian AA (March 1969). "The synthesis of O-methylnordehydrobufotenine, a new psychoactive indole". Journal of Medicinal Chemistry. 12 (2): 321–322. doi:10.1021/jm00302a030. PMID 4977410. Because of the high CNS activity shown by N,N-dimethyl-5-methoxytryptamine, the synthesis of the structurally related tricyclic indole, O-methylnordehydrobufotenine (6-methoxy-5-methyl-1,3,4,5-tetrahydropyrrolo[4,3,2-d,e]quinoline, IIc), was undertaken. [...] Pharmacologic activity was determined in squirrel monkeys trained in the Wisconsin General Test Apparatus [...] The median effective dose (ED50) of IIc that disrupted the ability to discriminate between disks of different sizes was 33.8 μmoles/kg.12 In this test, the O-methylnordehydrobufotenine (IIc) is approximately twice as active as mescaline (ED50 71.0 μmoles/kg),11 but is much less active than its open-chain analog, N,N-dimethyl-5-methoxytryptamine, which from published data5,8 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, IIc at 20 mg/kg causes only slight overt changes (reduction in spontaneous activity) while N,N-dimethyl-5-methoxytryptamine 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.
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