Harmol

Harmol

Names
IUPAC name 1-Methyl-2,9-dihydropyrido[3,4-b]indol-7-one
Identifiers
CAS Number	487-03-6^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:192558
ChEMBL	ChEMBL14285
ChemSpider	10296888
ECHA InfoCard	100.006.951
EC Number	207-645-9
PubChem CID	68094
UNII	7PQ075MCA6^Y
CompTox Dashboard (EPA)	DTXSID10960989 DTXSID10876697, DTXSID10960989
InChI InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,13-14H,1H3 Key: LBBJNGFCXDOYMQ-UHFFFAOYSA-N
SMILES CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1
Properties
Chemical formula	C12H10N2O
Molar mass	198.225 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Harmol is a chemical compound classified as a β-carboline.^[1][2][3] It is readily formed in vivo in humans by O-demethylation of harmine.^[4] Its elimination half-life has been reported to be about 1.5 to 2.0 hours.^[5][6]

See also

• Substituted β-carboline
• Harmalol

References

1. Abe A, Kokuba H (2013). "Harmol induces autophagy and subsequent apoptosis in U251MG human glioma cells through the downregulation of survivin". Oncol Rep. 29 (4): 1333–42. doi:10.3892/or.2013.2242. PMID 23338618.
2. El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO (2012). "Transcriptional and posttranslational inhibition of dioxin-mediated induction of CYP1A1 by harmine and harmol". Toxicol Lett. 208 (1): 51–61. Bibcode:2012ToxL..208...51E. doi:10.1016/j.toxlet.2011.09.030. PMC 3263333. PMID 22001777.
3. Abe A, Yamada H, Moriya S, Miyazawa K (2011). "The β-carboline alkaloid harmol induces cell death via autophagy but not apoptosis in human non-small cell lung cancer A549 cells". Biol Pharm Bull. 34 (8): 1264–72. doi:10.1248/bpb.34.1264. PMID 21804216.
4. Morales-Garcia JA, de la Fuenta Revenga M, Alonso-Gil S, Rodriguez-Franco MI, Feiding A, Perez-Castillo A, Riba J (2017). "The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro". Sci. Rep. 7 (1) 5309. Bibcode:2017NatSR...7.5309M. doi:10.1038/s41598-017-05407-9. PMC 5509699. PMID 28706205.
5. Brito-da-Costa AM, Dias-da-Silva D, Gomes NG, Dinis-Oliveira RJ, Madureira-Carvalho Á (October 2020). "Toxicokinetics and Toxicodynamics of Ayahuasca Alkaloids N,N-Dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: Clinical and Forensic Impact". Pharmaceuticals (Basel). 13 (11): 334. doi:10.3390/ph13110334. PMC 7690791. PMID 33114119.
6. Mueller MJ, Aicher HD, Dornbierer DA, Marten L, Suay D, Meling D, Elsner C, Wicki IA, Müller J, Poetzsch SN, Caflisch L, Hempe A, Steinhart CP, Puchkov M, Kost J, Landolt HP, Seifritz E, Quednow BB, Scheidegger M (December 2024). "Pharmacokinetics and pharmacodynamics of an innovative psychedelic N,N-dimethyltryptamine/harmine formulation in healthy participants: a randomized controlled trial". Int J Neuropsychopharmacol. 28 (1) pyaf001. doi:10.1093/ijnp/pyaf001. PMC 11770821. PMID 39774840.