Harmalol

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Wikipedia

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.616 Edit this at Wikidata
EC Number
  • 208-375-4
UNII
  • 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
  • OC1=CC=C(C(CCN=C3C)=C3N2)C2=C1
Properties
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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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]

See also

References

  1. ↑ Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.
  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.
  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.
  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.
  5. 1 2 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534