From Wikipedia, the free encyclopedia
Chemical compound
Tetrahydroharmine
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
AU :
S9 (Prohibited substance)
7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Formula C 13 H 16 N 2 O
Molar mass 216.284 g·mol−1 3D model (
JSmol )
CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC
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]
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. caapi' s
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.
[5]
See also
References
^ 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 .
^
a
b
"Poisons Standard October 2015" . Australian Government Department of Health. September 2015.
Further reading