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
17019-01-1 N
3DMet B02865
Abbreviations THH
ChEBI CHEBI:311931 YesY
ChEMBL ChEMBL129208 YesY
ChemSpider 140510 YesY
Jmol 3D model Interactive 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
Pharmacology
Legal status
  • AU: S9 (Prohibited)
Hazards
Flash point 195.2 °C (383.4 °F; 468.3 K)
Except where otherwise noted, data are 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.

Legal Status[edit]

Australia[edit]

Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[3] 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.[3]

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. 
  3. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

Further reading[edit]