Tetrahydroharmine

Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi.[1] THH weakly inhibits serotonin reuptake.[2]

Tetrahydroharmine
Names
IUPAC name
(1R)-7-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
Systematic IUPAC name
7-Methoxy-1-methyl-2,3,4,9-tetrahydro-1H-β-carboline
Other names
1,2,3,4-Tetrahydroharmine; Leptaflorine; 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido(3,4-b)indole
Identifiers
3D model (JSmol)
3DMet
Abbreviations THH
ChEBI
ChEMBL
ChemSpider
KEGG
MeSH Tetrahydroharmine
UNII
Properties
C13H16N2O
Molar mass 216.284 g·mol−1
Basicity (pKb) 10.334
Pharmacology
Legal status
  • AU: S9 (Prohibited substance)
Hazards
Flash point 195.2 °C (383.4 °F; 468.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

THH itself does not inhibit monoamine oxidase. However other harmala alkaloids in B. caapi, namely harmaline and harmine, are reversible inhibitors of monoamine oxidase A. While THH may not play a significant role in the inhibition of MAO it may contribute psychoactivity as a serotonin reuptake inhibitor.[2]

Australia

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[3] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[3]

See also

References
  1. Callaway, James C. (June 2005). "Various alkaloid profiles in decoctions of Banisteriopsis caapi" (PDF). Journal of Psychoactive Drugs. 37 (2): 151–5. doi:10.1080/02791072.2005.10399796. ISSN 0279-1072. PMID 16149328. Retrieved 2012-08-10.
  2. Callaway, James C.; McKenna, Dennis; Grob, Charles S.; et al. (June 1999). "Pharmacokinetics of hoasca alkaloids in healthy humans". Journal of Ethnopharmacology. 65 (3): 243–56. doi:10.1016/S0378-8741(98)00168-8. ISSN 0279-1072. PMID 10404423.
  3. Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

Further reading
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