Harmalol

Harmalol
Names
	Preferred IUPAC name 1-Methyl-4,9-dihydro-3H-pyrido[4,3-b]indol-7-ol
	Other names 1-Methyl-4,9-dihydro-3H-β-carbolin-7-ol
Identifiers
CAS Number	525-57-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	11262879;
ECHA InfoCard	100.007.616
EC Number	208-375-4;
PubChem CID	5353656;
UNII	2NQN80556Q ;
CompTox Dashboard (EPA)	DTXSID90975692 DTXSID50894870, DTXSID90975692 ;
	InChI InChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3 Key: RHVPEFQDYMMNSY-UHFFFAOYSA-N;
	SMILES OC1=CC=C(C(CCN=C3C)=C3N2)C2=C1;
Properties
Chemical formula	C12H12N2O
Molar mass	200.241 g·mol−1
Appearance	Red solid[citation needed]
Melting point	100 to 105 °C (212 to 221 °F; 373 to 378 K) (trihydrate)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Harmalol is a bioactive β-carboline and a member of the harmala alkaloids.^[2]^[3]

Pharmacology

Pharmacokinetics

The elimination half-life of harmalol has been reported to be 30 to 49 hours.^[4]

Society and culture

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]

Canada

Harmalol is a controlled substance in Canada.^[6]

References

↑ Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.
↑ Sarkar S, Bhadra K (2014). "Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach". J Photochem Photobiol B. 130: 272–80. Bibcode:2014JPPB..130..272S. doi:10.1016/j.jphotobiol.2013.11.021. PMID 24368411.
↑ El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO (2012). "Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms". Food Chem Toxicol. 50 (2): 353–62. doi:10.1016/j.fct.2011.10.052. PMC 3281145. PMID 22037238.
↑ 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.
1 2 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[1] Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.

[pmid24368411-2] Sarkar S, Bhadra K (2014). "Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach". J Photochem Photobiol B. 130: 272–80. Bibcode:2014JPPB..130..272S. doi:10.1016/j.jphotobiol.2013.11.021. PMID 24368411.

[pmid22037238-3] El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO (2012). "Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms". Food Chem Toxicol. 50 (2): 353–62. doi:10.1016/j.fct.2011.10.052. PMC 3281145. PMID 22037238.

[Brito-da-CostaDias-da-SilvaGomes2020-4] 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.

[Poisons_Standard-5] 1 2 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

[CDSA-6] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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