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6-MeO-THH

Chemical compound


Chemical compound

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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). 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. The compound has been isolated from certain plants of the Virola family.

Use and effects

6-MeO-THH is reported to be hallucinogenic similarly to other β-carbolines like harmaline. Limited testing suggests that it possesses mild psychoactive effects at a dose of 1.5mg/kg (~100mg 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. Its dose range and duration are unknown.

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.

Chemistry

Synthesis

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

Society and culture

Canada

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

References

References

  1. (1975). "Hallucinogenic Agents". Wright-Scientechnica.
  2. (April 1998). "Investigation of hallucinogenic and related beta-carbolines". Drug and Alcohol Dependence.
  3. (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.
  4. (October 2001). "beta-carboline binding to imidazoline receptors". Drug and Alcohol Dependence.
  5. {{CiteTiHKAL https://www.erowid.org/library/books_online/tihkal/tihkal44.shtml
  6. "Controlled Drugs and Substances Act".
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