6-MeO-THH, also known as 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a

pinoline Pinoline is a β-carboline and methoxylated tryptoline (5-methoxytryptoline) long claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial. Its IUPAC name is 6-methoxy-1, ...

) derivative and a structural isomer of

tetrahydroharmine Tetrahydroharmine (THH) is a fluorescent indole alkaloid and β-carboline that occurs in the tropical liana species ''Banisteriopsis caapi''. Effects THH has been reported to produce psychoactive effects similar to those of harmaline in human ...

(7-MeO-THH). It is mentioned in Alexander Shulgin's book ''

TiHKAL ''TiHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PiHKAL: A Chemical Love Story'', ''TiHKAL'' is an acronym that stands for "Trypt ...

'' (''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 ''Virola'' is a genus of flowering plants in the nutmeg family, Myristicaceae. It includes medium-sized trees native to rainforests of the tropical Americas, ranging from southern Mexico to Bolivia and southern Brazil. Species are known commonl ...

'' family.

Effects

6-MeO-THH is reported to be

hallucinogen Hallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a large and diverse class of psychoactive drugs that can produce altered states of consciousness characterized by major alterations in thought, mo ...

ic similarly to other β-carbolines like

harmaline Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a fluorescent indole alkaloid from the group of harmala alkaloids and β-carbolines. It is the partly hydrogenated form of harmine. It is a rever ...

. Limited testing suggests that it possesses mild

psychoactive A psychoactive drug, psychopharmaceutical, mind-altering drug, consciousness-altering drug, psychoactive substance, or psychotropic substance is a chemical substance that alters psychological functioning by modulating central nervous system acti ...

effects at a dose of 1.5mg/kg orally and is said to be about one-third as potent as

6-methoxyharmalan 6-Methoxyharmalan, or 6-methoxyharmalane, also known as 6-methoxy-1-methyl-3,4-dihydro-β-carboline, is a naturally occurring serotonin receptor modulator, monoamine oxidase inhibitor, and hallucinogen of the β-carboline family related to harm ...

and three times as potent as harmaline.

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 receptor The GABAA receptor (GABAAR) is an ionotropic receptor and ligand-gated ion channel. Its endogenous Ligand (biochemistry), ligand is γ-aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Accurate regul ...

s, and

imidazoline receptor Imidazoline receptors are the primary receptors on which clonidine and other imidazolines act. There are three main classes of imidazoline receptor: I1 is involved in inhibition of the sympathetic nervous system to lower blood pressure, I2 has ...

References

{{Tryptamines Beta-Carbolines Hallucinogens 5-Methoxytryptamines N-Monoalkyltryptamines Serotonin receptor modulators

Effects

Pharmacology

See also

References