Tetrahydroharmine

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Tetrahydroharmine
2D diagram of the chemical structure of tetrahydroharmine
3D diagram of the chemical structure of 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
17019-01-1 N
ChEBI CHEBI:311931 YesY
ChEMBL ChEMBL129208 YesY
ChemSpider 140510 YesY
Jmol-3D images Image
KEGG C09243 YesY
MeSH Tetrahydroharmine
PubChem 159809
Properties
C
13
H
16
N
2
O
Molar mass 216.279 g/mol
Boiling point 399.2 °C (750.6 °F; 672.3 K)
Basicity (pKb) 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]

Two other harmala alkaloids in B. caapi, harmaline and harmine, are reversible inhibitors of monoamine oxidase A. Tetrahydroharmine, however, does not inhibit monoamine oxidase B.

See also[edit]

References[edit]

  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. 

Further reading[edit]