6-MeO-THH

6-MeO-THH

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Systematic (IUPAC) name
6-methoxy-1-methyl-2,3,4,9- tetrahydro-1H-pyrido[3,4-b]indole
Identifiers
CAS Number	1210-56-6 Y
PubChem	CID: 71028
ChemSpider	64188 Y
ChEMBL	CHEMBL221811 Y
Chemical data
Formula	C13H16N2O
Molecular mass	216.278 g/mol
SMILES CC1NCCC2=C1[N]C(C=C3)=C2C=C3OC
InChI InChI=1S/C13H16N2O/c1-8-13-10(5-6-14-8)11-7-9(16-2)3-4-12(11)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3 Y Key:RDUORFDQRFHYBF-UHFFFAOYSA-N Y
Physical data
Melting point	152–155 °C (306–311 °F)
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6-MeO-THH, or 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of leptaflorine (7-MeO-THH). 6-MeO-THH is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), stating that 6-MeO-THH is very similar to the other carbolines. Limited testing suggests that it possesses mild psychoactive effects at 1.5 mg/kg and is said to be about one-third as potent as 6-methoxyharmalan. It has been isolated from certain plants of the Virola family.

Pharmacology

Very little is known about the psychoactivity of 6-MeO-THH in humans. Studies in rats have shown it to bind to a number of serotonin (5-HT1 receptors and 5-HT2 receptors), dopamine (D2), benzodiazepine and imidazoline receptors.

See also

• Beta-carboline
• Harmala alkaloid
• Tryptamine