Tetrahydroharmol

Tetrahydroharmol
Clinical data
Other names	1,2-Dihydroharmaline
Identifiers
	IUPAC name 1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-ol;
CAS Number	17952-75-9;
PubChem CID	368982;
ChemSpider	327573;
UNII	DHR7GV467K;
ChEMBL	ChEMBL14122;
CompTox Dashboard (EPA)	DTXSID101027096 ;
Chemical and physical data
Formula	C12H14N2O
Molar mass	202.257 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)O;
	InChI InChI=1S/C12H14N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6-7,13-15H,4-5H2,1H3; Key:AZTMWIPCEFFOJD-UHFFFAOYSA-N;

Tetrahydroharmol is a bioactive beta-carboline harmala alkaloid.^[1] It acts as a reversible inhibitor of monoamine oxidase A.^[2]

Legal Status

Australia

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]

References

^ Riba J, McIlhenny EH, Valle M, Bouso JC, Barker SA (2012). "Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca". Drug Testing and Analysis. 4 (7–8): 610–616. doi:10.1002/dta.1344. PMID 22514127.
^ 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.
^ ^a ^b "Poisons Standard October 2015". Australian Government Department of Health. September 2015.

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[1] Riba J, McIlhenny EH, Valle M, Bouso JC, Barker SA (2012). "Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca". Drug Testing and Analysis. 4 (7–8): 610–616. doi:10.1002/dta.1344. PMID 22514127.

[Buckholtz_Boggan_1977_pp._1991–1996-2] 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.

[Poisons_Standard-3] "Poisons Standard October 2015". Australian Government Department of Health. September 2015.

[1]

[2]

[3]

Legal Status

Australia

See also

References