Harmalacidine

Harmalacidine
Clinical data
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
Identifiers
  • 7-methoxy-2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H12N2O2
Molar mass216.240 g·mol−1
3D model (JSmol)
  • COC1=CC2=C(C=C1)C3=C(N2)C(=O)NCC3
  • 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

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][5]

See also

References

  1. ^ a b c d Alossaimi MA, ElNaggar MH, Magdy G, Mourenza Á, Mateos L, Letek M, et al. (February 2026). "Ultrasensitive spectrofluorimetric analysis of harmalacidine HCl: A potent underexplored MAO-A inhibitor from Peganum harmala L". Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy. 347 127056. Bibcode:2026AcSpA.34727056A. doi:10.1016/j.saa.2025.127056. PMID 41108932.
  2. ^ Hashimoto Y, Kawanishi K (1976). "New alkaloids from Banisteriopsis caapi". Phytochemistry. 15 (10): 1559–1560. Bibcode:1976PChem..15.1559H. doi:10.1016/S0031-9422(00)88936-0.
  3. ^ Siddiqui S, Yusuf Khan O, Faizi S, Shaheen Siddiqui B (1988). "Studies in the Chemical Constituents of the Seeds of Pegnum harmala: Isolation and Structure Elucidation of Two b-Carboline Lactams - Harmalanine and Harmalacidine". Heterocycles. 27 (6): 1401. doi:10.3987/COM-88-4490. ISSN 0385-5414.
  4. ^ Lamchouri F, Toufik H, Bouzzine SM, Hamidi M, Bouachrine M (2010). "Experimental and computational study of biological activities of alkaloids isolated from Peganum harmala seeds" (PDF). J Mater Environ Sci. 1 (Suppl 1): 343–352.
  5. ^ Wang C, Zhang Z, Wang Y, He X (November 2015). "Cytotoxic indole alkaloids against human leukemia cell lines from the toxic plant Peganum harmala". Toxins. 7 (11): 4507–4518. doi:10.3390/toxins7114507. PMC 4663518. PMID 26540074.
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