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3-AMTBI

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From Wikipedia, the free encyclopedia
3-AMTBI
Clinical data
Other names3-Aminomethyl-1,3,4,5-tetrahydrobenz(cd)indole; 4,β-Dimethylenetryptamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1,3,4,5-tetrahydrobenzo[cd]indol-3-ylmethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H14N2
Molar mass186.258 g·mol−1
3D model (JSmol)
  • C1CC2=C3C(=CC=C2)NC=C3C1CN
  • InChI=1S/C12H14N2/c13-6-9-5-4-8-2-1-3-11-12(8)10(9)7-14-11/h1-3,7,9,14H,4-6,13H2
  • Key:PKWJZQKTYSEOEQ-UHFFFAOYSA-N

3-AMTBI, also known as 3-aminomethyl-1,3,4,5-tetrahydrobenz(cd)indole or as 4,β-dimethylenetryptamine, is a serotonin receptor modulator of the tryptamine family.[1][2] It is a cyclized tryptamine and is the derivative of tryptamine in which the 4 and β positions have been connected with an ethyl group, resulting in a non-partial ergoline tricyclic compound.[1][2] The drug shows affinity for the serotonin 5-HT1, 5-HT1A, and 5-HT2A receptors (Ki = 392 nM, 369 nM, and 555 nM, respectively).[1][2] It showed several-fold higher affinity for the serotonin 5-HT2A receptor than tryptamine and about the same affinity as dimethyltryptamine (DMT).[1][2] The chemical synthesis of 3-AMTBI has been described.[3][2] 3-AMTBI was first described in the scientific literature by E. W. Taylor and colleagues by 1987.[1][2]

See also

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References

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  1. 1 2 3 4 5 Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320.
  2. 1 2 3 4 5 6 Taylor EW, Nikam S, Weck B, Martin A, Nelson D (October 1987). "Relative selectivity of some conformationally constrained tryptamine analogs at 5-HT1, 5-HT1A and 5-HT2 recognition sites". Life Sci. 41 (16): 1961–1969. doi:10.1016/0024-3205(87)90749-1. PMID 3657392.
  3. ↑ Bartoccini, Francesca; Piersanti, Giovanni (2021). "Synthesis and Reactivity of Uhle's Ketone and Its Derivatives". Synthesis. 53 (08): 1396–1408. doi:10.1055/a-1340-3423. ISSN 0039-7881. Retrieved 3 October 2026.
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