Tetrahydroharmine

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; 1H-Pyrido(3,4-B)indole, 2,3,4,9-tetrahydro-7-methoxy-1-methyl- (VAN)
Identifiers
3DMet	B02865
Abbreviations	THH
CAS Registry Number	17019-01-1^N
ChEBI	CHEBI:311931^Y
ChEMBL	ChEMBL129208^Y
ChemSpider	140510^Y
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^Y Key: ZXLDQJLIBNPEFJ-UHFFFAOYSA-N^Y 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
Jmol-3D images	Image
KEGG	C09243^Y
MeSH	Tetrahydroharmine
PubChem	159809
SMILES COc1cc2CCn3c(cc4c(cncc4c3=O)[C@@H](C)O)-c2cc1O
Properties
Chemical formula	C 13H 16N 2O
Molar mass	216.279 g/mol
Boiling point	399.2 °C (750.6 °F; 672.3 K)
Basicity (pK_b)	10.334
Hazards
Flash point	195.2 °C (383.4 °F; 468.3 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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

References

↑ 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.
↑ 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. |accessdate= requires |url= (help)