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MTHPI

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(Redirected from 5-MeO-MTHPI)

MTHPI
Clinical data
Other names3-MTPI; 3-(1-Methyl-1,2,3,6-tetrahydropyrid-4-yl)indole; N′-Methyl-THPI
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indole
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC14H16N2
Molar mass212.296 g·mol−1
3D model (JSmol)
  • CN1CCC(=CC1)C2=CNC3=CC=CC=C32
  • InChI=1S/C14H16N2/c1-16-8-6-11(7-9-16)13-10-15-14-5-3-2-4-12(13)14/h2-6,10,15H,7-9H2,1H3
  • Key:IUENQRYBZHHPBN-UHFFFAOYSA-N

MTHPI, also known as 3-(1-methyl-1,2,3,6-tetrahydropyrid-4-yl)indole (3-MTPI), is a serotonin receptor modulator of the tetrahydropyridinylindole group related to the psychedelic drug dimethyltryptamine (DMT).[1][2] Though it is not technically a tryptamine itself, MTHPI can be regarded as a constrained analogue of DMT.[1][2]

The drug shows affinity for the serotonin 5-HT1, 5-HT1A, and 5-HT2A receptors (Ki = 217 nM, 144 nM, and 71 nM, respectively).[1][2] Its affinity for the serotonin 5-HT2A receptor was 8-fold higher than that of DMT.[1][2] Besides serotonin receptors, MTHPI also shows affinity for the serotonin transporter (SERT) (IC50Tooltip half-maximal inhibitory concentration = 690 nM).[3]

The chemical synthesis of MTHPI has been described.[2] Derivatives of MTHPI such as 5-MeO-MTHPI, 2-Me-MTHPI, and 5-MeO-2-Me-MTHPI have also been described.[2] 5-MeO-MTHPI showed 11-fold lower affinity for the serotonin 5-HT2A receptor and 6-fold higher affinity for the serotonin 5-HT1A receptor compared to MTHPI.[2] Conversely, the 2-methylated analogues showed markedly reduced affinities for the assessed serotonin receptors.[1][2] Various other derivatives of MTHPI, acting as monoamine transporter modulators, have been described as well.[3]

MTHPI was first described in the scientific literature by E. W. Taylor and colleagues by 1987.[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 7 8 9 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 Sciences. 41 (16): 1961–1969. doi:10.1016/0024-3205(87)90749-1. PMID 3657392.
  3. 1 2 Deskus JA, Epperson JR, Sloan CP, Cipollina JA, Dextraze P, Qian-Cutrone J, et al. (June 2007). "Conformationally restricted homotryptamines 3. Indole tetrahydropyridines and cyclohexenylamines as selective serotonin reuptake inhibitors". Bioorganic & Medicinal Chemistry Letters. 17 (11): 3099–3104. doi:10.1016/j.bmcl.2007.03.040. PMID 17391962.
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