Pharm-136

From Wikipedia, the free encyclopedia

Other names"Compound #1"; "Cpd #1";[1][2] 5-HT2C agonist-11;[3] 7-Methyl-10-hydroxynoribogaminalog
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
CAS Number
Pharm-136
Clinical data
Other names"Compound #1"; "Cpd #1";[1][2] 5-HT2C agonist-11;[3] 7-Methyl-10-hydroxynoribogaminalog
Drug classSerotonin 5-HT2 receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 7-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indol-10-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
  • CC1=C2C(=C(C=C1)O)C3=C(N2)CCNCC3
  • InChI=1S/C13H16N2O/c1-8-2-3-11(16)12-9-4-6-14-7-5-10(9)15-13(8)12/h2-3,14-16H,4-7H2,1H3
  • Key:IMUNBYGTPDZBIR-UHFFFAOYSA-N

Pharm-136, also known as 7-methyl-10-hydroxynoribogaminalog, is a serotonin 5-HT2 receptor agonist and psychedelic drug of the ibogalog family.[1][2]

Pharmacodynamics

Pharm-136 acts as a potent serotonin 5-HT2 receptor agonist, with EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) values of 0.6 nM (102%) at the serotonin 5-HT2A receptor, 3.5 nM (52%) at the serotonin 5-HT2B receptor, and 0.5 nM (101%) at the serotonin 5-HT2C receptor.[1][2] The drug showed far lower agonistic potency or was inactive at all other serotonin receptors.[2] As an agonist of the serotonin 5-HT2A receptor in vitro, Pharm-136 showed 29-fold greater potency as well as higher efficacy (101% vs. 80%) than psilocin.[2]

The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2] Its median effective dose (ED50) was 3.6 mg/kg, compared to 0.38 mg/kg (9.5-fold lower) in the case of psilocybin.[2]

Pharmacokinetics

The preclinical pharmacokinetics of Pharm-136 have been studied.[2]

Chemistry

Pharm-136 is an ibogalog (azepinoindole) derivative and a cyclized tryptamine analogue of the non-hallucinogenic psychoplastogen 7-methylpsilocin.[1][2]

Synthesis

The chemical synthesis of Pharm-136 has been described.[2]

History

See also

References

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