Tetrahydroharmine

Tetrahydroharmine
Clinical data
Other names	THH; 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
	IUPAC name 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole;
CAS Number	17019-01-1;
PubChem CID	159809;
ChemSpider	140510;
UNII	F1Q1E0G45A;
KEGG	C09243;
ChEBI	CHEBI:311931;
ChEMBL	ChEMBL129208;
Chemical and physical data
Formula	C13H16N2O
Molar mass	216.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC;
	InChI 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]

^ 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.
^ 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.
^ 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.
^ 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.