Tetrahydroharmine

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

Tetrahydroharmine
Clinical data
Other namesTHH; 1,2,3,4-Tetrahydroharmine; Leptaflorine; 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido(3,4-b)indole
Legal status
Legal status
  • AU: S9 (Prohibited substance)
Identifiers
  • 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
  • CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC
  • InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3
  • Key:ZXLDQJLIBNPEFJ-UHFFFAOYSA-N

THH, like other harmala alkaloids in B. caapi, namely harmaline and harmine, is a reversible inhibitor of monoamine oxidase A,[2] but it also inhibits the reuptake of serotonin.[3]

THH contributes to B. caapi's psychoactivity as a serotonin reuptake inhibitor.[4]

Australia

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[5] 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.[5]

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. S2CID 1420203. Retrieved 2012-08-10.
  2. Buckholtz, Neil S.; Boggan, William O. (1 November 1977). "Monoamine oxidase inhibition in brain and liver produced by β-carbolines: structure-activity relationships and substrate specificity". Biochemical pharmacology. Elsevier BV. 26 (21): 1991–1996. doi:10.1016/0006-2952(77)90007-7. ISSN 0006-2952. PMID 921812.
  3. Morales-García, Jose A.; de la Fuente Revenga, Mario; Alonso-Gil, Sandra; Rodríguez-Franco, María Isabel; Feilding, Amanda; Perez-Castillo, Ana; Riba, Jordi (13 July 2017). "The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro". Scientific Reports. Springer Science and Business Media LLC. 7 (1). doi:10.1038/s41598-017-05407-9. ISSN 2045-2322.
  4. 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.
  5. Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

Further reading
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