Harmalacidine

Harmalacidine, also known as 7-methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-one or as 1-keto-7-methoxytryptoline, is a harmala alkaloid and β-carboline found in Peganum harmala (Syrian rue) and Banisteriopsis caapi.^[1] It is a reversible inhibitor of monoamine oxidase A (RIMA), with similar potency as harmine (IC₅₀Tooltip half-maximal inhibitory concentration = 457 nM and 506 nM, respectively).^[1] The alkaloid was isolated from Banisteriopsis caapi in 1976 and from Peganum harmala in 1988.^[1][2][3] The amounts of harmalacidine in Peganum harmala seeds vary widely, ranging from milligram to gram quantities.^[1][4]

Other namesKetotetrahydronorharmine; Oxotetrahydronorharmine; 7-Methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-one; 1-Keto-7-methoxytryptoline

Drug classMonoamine oxidase inhibitor (MAOI); Reversible inhibitor of MAO-A (RIMA)

ATC code

• None

CAS Number

• 26579-69-1

Quick facts Clinical data, Other names ...

Harmalacidine

Clinical data
Other names	Ketotetrahydronorharmine; Oxotetrahydronorharmine; 7-Methoxy-2,3,4,9-tetrahydro-1H-β-carbolin-1-one; 1-Keto-7-methoxytryptoline
Drug class	Monoamine oxidase inhibitor (MAOI); Reversible inhibitor of MAO-A (RIMA)
ATC code	None
Identifiers
IUPAC name 7-methoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
CAS Number	26579-69-1
PubChem CID	179484
ChemSpider	156232
ChEMBL	ChEMBL4059776
CompTox Dashboard (EPA)	DTXSID20181148
Chemical and physical data
Formula	C12H12N2O2
Molar mass	216.240 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)C3=C(N2)C(=O)NCC3
InChI InChI=1S/C12H12N2O2/c1-16-7-2-3-8-9-4-5-13-12(15)11(9)14-10(8)6-7/h2-3,6,14H,4-5H2,1H3,(H,13,15) Key:MWEGNYFSTKOOSD-UHFFFAOYSA-N

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