6-Methoxyharman

6-Methoxyharman, also known as isoharmine, is a β-carboline and harmala alkaloid.^{[1][2][3][4][5]} It is an analogue of other β-carbolines like harman and 6-methoxyharmalan.^[6][7] The compound has been found to be naturally occurring in Peganum harmala and Virola species such as Virola cuspidata and Virola elongata.^{[5][3][8][9][10]} It is a potent monoamine oxidase inhibitor (MAOI).^[7] In addition, 6-methoxyharman has been found to bind to serotonin receptors, including the serotonin 5-HT_2C receptor (K_i = 3,700 nM), but notably not to the serotonin 5-HT_2A or 5-HT_1A receptors (K_i = >10,000).^[11][12][13] It may potentiate the effects of psychedelic tryptamines like dimethyltryptamine (DMT) via its MAOI activity, for instance when they are used as Virola-containing hallucinogenic snuffs.^[9] According to Alexander Shulgin, Claudio Naranjo might have tested the effects 6-methoxyharman in humans, but this is unclear.^[14][15]

6-Methoxyharman

Clinical data
Other names	Coharmine; Isoharmine; 6-Methoxyharmane; 6-MeO-harman; 6-OMe-harman; 6-Methoxy-1-methyl-β-carboline; 1-Methyl-6-methoxy-2-carboline
ATC code	None
Identifiers
IUPAC name 6-methoxy-1-methyl-9H-pyrido[3,4-b]indole
CAS Number	3589-72-8
PubChem CID	5376026
ChemSpider	4525389
UNII	48GQI7H930
ChEMBL	ChEMBL278193
CompTox Dashboard (EPA)	DTXSID40189449
Chemical and physical data
Formula	C13H12N2O
Molar mass	212.252 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=NC=CC2=C1NC3=C2C=C(C=C3)OC
InChI InChI=1S/C13H12N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-7,15H,1-2H3 Key:XYYVPBBISSKKQB-UHFFFAOYSA-N

See also

• Substituted β-carboline
• Harmala alkaloid