6-MeO-THH

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6-MeO-THH
6-MeO-THH.png
Identifiers
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C13H16N2O
Molar mass 216.278 g/mol
3D model (Jmol)
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 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[edit]

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.[2][3][4]

See also[edit]

References[edit]

  1. ^ Shulgin, Alexander; Ann Shulgin (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press, 425. ISBN 0-9630096-9-9. OCLC 38503252. 
  2. ^ a b Grella, Brian; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Herrick-Davis, Katharine; Gauthier, Colleen B; Glennon, Richard A (April 1998). "Investigation of hallucinogenic and related β-carbolines". Drug and Alcohol Dependence. 50 (2): 99–107. doi:10.1016/S0376-8716(97)00163-4. 
  3. ^ Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V. (August 2000). "Binding of β-carbolines and related agents at serotonin (5-HT2 and 5-HT1A), dopamine (D2) and benzodiazepine receptors". Drug and Alcohol Dependence. 60 (2): 121–132. doi:10.1016/S0376-8716(99)00148-9. 
  4. ^ Husbands, Stephen M.; Glennon, Richard A.; Gorgerat, Stephane; Gough, Rhianon; Tyacke, Robin; Crosby, John; Nutt, David J.; Lewis, John W.; Hudson, Alan L. (October 2001). "β-carboline binding to imidazoline receptors". Drug and Alcohol Dependence. 64 (2): 203–208. doi:10.1016/S0376-8716(01)00123-5.