6-MeO-THH, also known as 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).[2] It 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] The compound has been isolated from certain plants of the Virola family.[citation needed]

Use and effects

6-MeO-THH is reported to be hallucinogenic similarly to other β-carbolines like harmaline.[2] Limited testing suggests that it possesses mild psychoactive effects at a dose of 1.5 mg/kg (~100 mg for a 70-kg person) orally and is said to be about one-third as potent as 6-methoxyharmalan and three times as potent as harmaline.[2][3] Its dose range and duration are unknown.[1]

Pharmacology

Pharmacodynamics

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.[3][4][5]

Chemistry

Synthesis

The chemical synthesis of 6-MeO-THH has been described.[1]

Society and culture

Canada

6-MeO-THH is not a controlled substance in Canada as of 2025.[6]

See also

References

  1. 1 2 3 4 5 6 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. https://www.erowid.org/library/books_online/tihkal/tihkal44.shtml
  2. 1 2 3 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. [...] the apparent superiority of extracts of Banisteriopsis over the pure harmine prompted the suggestion (Hochstein and Paradies, 1957) that either harmaline or 1,2,3,4-tetrahydroharmine, or other as then unidentified constituents, were the psychoactive compounds. Naranjo (1967) has now confirmed their hallucinogenic activity in man together with that of 6-methoxyharmalan and 6-methoxytetrahydroharman. [...] 6-Methoxytetrahydroharman (4.34) was also psychoactive, eliciting mild subjective changes at 1·5 mg./kg. (p.o.), but being only three times as potent as harmaline.
  3. 1 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.
  4. ↑ 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. hdl:11380/17721. PMID 10940539.
  5. ↑ 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. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
source: https://en.wikipedia.org/wiki/6-MeO-THH