Tetrahydroharmine Explained
| Drug Name: | Tetrahydroharmine |
| Legal Au: | Schedule 9 |
| Cas Number: | 17019-01-1 |
| Pubchem: | 159809 |
| Chemspiderid: | 140510 |
| Unii: | F1Q1E0G45A |
| Kegg: | C09243 |
| Chebi: | 311931 |
| Chembl: | 129208 |
| Synonyms: | THH; 1,2,3,4-Tetrahydroharmine; Leptaflorine; 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido(3,4-b)indole |
| Iupac Name: | 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole |
| C: | 13 |
| H: | 16 |
| N: | 2 |
| O: | 1 |
| Smiles: | CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC |
| Stdinchi: | 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 |
| Stdinchikey: | 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. caapis psychoactivity as a serotonin reuptake inhibitor.[4]
Legal Status
Australia
Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015).[5] 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.
See also
Further reading
- Web site: Tetrahydroharmine . Shulgin A . Alexander Shulgin . 1997 . . 10 August 2012.
Notes and References
- Callaway JC . Various alkaloid profiles in decoctions of Banisteriopsis caapi . Journal of Psychoactive Drugs . 37 . 2 . 151–155 . June 2005 . 16149328 . 10.1080/02791072.2005.10399796 . 1420203 .
- Buckholtz NS, Boggan WO . Monoamine oxidase inhibition in brain and liver produced by beta-carbolines: structure-activity relationships and substrate specificity . Biochemical Pharmacology . 26 . 21 . 1991–1996 . November 1977 . 921812 . 10.1016/0006-2952(77)90007-7 . Elsevier BV .
- Morales-García JA, de la Fuente Revenga M, Alonso-Gil S, Rodríguez-Franco MI, Feilding A, Perez-Castillo A, Riba J . The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro . Scientific Reports . 7 . 1 . 5309 . July 2017 . 28706205 . 10.1038/s41598-017-05407-9 . Springer Science and Business Media LLC . free . 5509699 . 2017NatSR...7.5309M .
- Callaway JC, McKenna DJ, Grob CS, Brito GS, Raymon LP, Poland RE, Andrade EN, Andrade EO, Mash DC . 6 . Pharmacokinetics of Hoasca alkaloids in healthy humans . Journal of Ethnopharmacology . 65 . 3 . 243–256 . June 1999 . 10404423 . 10.1016/S0378-8741(98)00168-8 . Dennis McKenna .
- Web site: Poisons Standard October 2015 . September 2015 . Australian Government Department of Health .
