Tetrahydroharmine

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
CompTox Dashboard (EPA)
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

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

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

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

  1. ^ Callaway JC (June 2005). "Various alkaloid profiles in decoctions of Banisteriopsis caapi". Journal of Psychoactive Drugs. 37 (2): 151–155. doi:10.1080/02791072.2005.10399796. PMID 16149328. S2CID 1420203.
  2. ^ Buckholtz NS, Boggan WO (November 1977). "Monoamine oxidase inhibition in brain and liver produced by beta-carbolines: structure-activity relationships and substrate specificity". Biochemical Pharmacology. 26 (21). Elsevier BV: 1991–1996. doi:10.1016/0006-2952(77)90007-7. PMID 921812.
  3. ^ Morales-García JA, de la Fuente Revenga M, Alonso-Gil S, Rodríguez-Franco MI, Feilding A, Perez-Castillo A, Riba J (July 2017). "The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro". Scientific Reports. 7 (1). Springer Science and Business Media LLC: 5309. Bibcode:2017NatSR...7.5309M. doi:10.1038/s41598-017-05407-9. PMC 5509699. PMID 28706205.
  4. ^ Callaway JC, McKenna DJ, Grob CS, Brito GS, Raymon LP, Poland RE, et al. (June 1999). "Pharmacokinetics of Hoasca alkaloids in healthy humans". Journal of Ethnopharmacology. 65 (3): 243–256. doi:10.1016/S0378-8741(98)00168-8. PMID 10404423.