6-MeO-THH

6-MeO-THH
Identifiers
	IUPAC name 6-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;
CAS Number	1210-56-6 ;
PubChem CID	71028;
ChemSpider	64188 ;
UNII	U18P8J9O2I;
ChEMBL	ChEMBL221811 ;
CompTox Dashboard (EPA)	DTXSID20871835 ;
Chemical and physical data
Formula	C13H16N2O
Molar mass	216.284 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	152–155 °C (306–311 °F)
	SMILES CC1NCCC2=C1NC(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 ; Key:RDUORFDQRFHYBF-UHFFFAOYSA-N ;
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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 tetrahydroharmine (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.[1] 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.[2] 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 receptors, benzodiazepine receptors, and imidazoline receptors.[2][3][4]

References

Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 425. ISBN 0-9630096-9-9. OCLC 38503252.
Grella B, Dukat M, Young R, Teitler M, Herrick-Davis K, Gauthier CB, Glennon RA (April 1998). "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence. 50 (2): 99–107. doi:10.1016/S0376-8716(97)00163-4. PMID 9649961.
Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence. 60 (2): 121–32. doi:10.1016/S0376-8716(99)00148-9. PMID 10940539.
Husbands SM, Glennon RA, Gorgerat S, Gough R, Tyacke R, Crosby J, et al. (October 2001). "beta-carboline binding to imidazoline receptors". Drug and Alcohol Dependence. 64 (2): 203–8. doi:10.1016/S0376-8716(01)00123-5. PMID 11543990.

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[1] Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 425. ISBN 0-9630096-9-9. OCLC 38503252.

[Brian1-2] Grella B, Dukat M, Young R, Teitler M, Herrick-Davis K, Gauthier CB, Glennon RA (April 1998). "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence. 50 (2): 99–107. doi:10.1016/S0376-8716(97)00163-4. PMID 9649961.

[3] Glennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors". Drug and Alcohol Dependence. 60 (2): 121–32. doi:10.1016/S0376-8716(99)00148-9. PMID 10940539.

[4] Husbands SM, Glennon RA, Gorgerat S, Gough R, Tyacke R, Crosby J, et al. (October 2001). "beta-carboline binding to imidazoline receptors". Drug and Alcohol Dependence. 64 (2): 203–8. doi:10.1016/S0376-8716(01)00123-5. PMID 11543990.

6-MeO-THH

Pharmacology

See also

References