6-Methoxyharmalan

6-Methoxyharmalan
Clinical data
Other names6-Methoxyharmalane; 6-Methoxy-1-methyl-3,4-dihydro-β-carboline; 10-Methoxyharmalan; 6-MeO-harmalan; 6-OMe-harmalan
Routes of
administration		Oral, intravenous injection
Drug classSerotonin receptor modulator; Monoamine oxidase inhibitor; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Onset of actionOral: 1 hour
IVTooltip Intravenous injection: almost immediate
Identifiers
  • 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H14N2O
Molar mass214.268 g·mol−1
3D model (JSmol)
  • CC1=NCCC2=C1NC3=C2C=C(C=C3)OC
  • InChI=1S/C13H14N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-4,7,15H,5-6H2,1-2H3
  • Key:HMBHRMFLDKKSCT-UHFFFAOYSA-N

6-Methoxyharmalan, or 6-methoxyharmalane, also known as 6-methoxy-1-methyl-3,4-dihydro-β-carboline, is a naturally occurring serotonin receptor modulator, monoamine oxidase inhibitor, and hallucinogen of the β-carboline family related to harmaline (7-methoxyharmalan). It is a cyclized tryptamine and analogue of 5-MeO-DMT and melatonin (N-acetyl-5-methoxytryptamine). The compound has been isolated from Virola species.

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