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6-MeO-THH

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
6-MeO-THH
Clinical data
Other names6-Methoxy-1,2,3,4-tetrahydroharman; 6-Methoxytetrahydroharman
Routes of
administration		Oral[1]
Drug classHallucinogen;Oneirogen;Serotonin receptor modulator
ATC code
  • None
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • 6-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
Melting point152–155 °C (306–311 °F)
  • CC1NCCC2=C1NC(C=C3)=C2C=C3OC
  • 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 checkY
  • Key:RDUORFDQRFHYBF-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

6-MeO-THH, also known as6-methoxy-1,2,3,4-tetrahydroharman, is aβ-carboline (or more specifically apinoline) derivative and a structural isomer oftetrahydroharmine (7-MeO-THH).[2] It is mentioned in Alexander Shulgin's bookTiHKAL (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 theVirola family.[citation needed]

Use and effects

[edit]

6-MeO-THH is reported to behallucinogenic similarly to other β-carbolines likeharmaline.[2] Limited testing suggests that it possesses mildpsychoactive 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 as6-methoxyharmalan and three times as potent as harmaline.[2][3] Its dose range andduration are unknown.[1]

Pharmacology

[edit]

Pharmacodynamics

[edit]

Very little is known about thepsychoactivity of 6-MeO-THH in humans. Studies in rats have shown it to bind to a number of serotonin5-HT1 receptors and5-HT2 receptors, dopamineD2 receptors,benzodiazepine receptors, andimidazoline receptors.[3][4][5]

Chemistry

[edit]

Synthesis

[edit]

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

See also

[edit]

References

[edit]
  1. ^abcdefShulgin, 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. ^abcBrimblecombe 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. ^abGrella 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.

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