Harmine

Harmine
Names
Preferred IUPAC name
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.485 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3 checkY
    Key: BXNJHAXVSOCGBA-UHFFFAOYSA-N checkY
  • InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
    Key: BXNJHAXVSOCGBA-UHFFFAOYAR
  • COc1ccc2c(c1)[nH]c3c(C)nccc23
Properties
C13H12N2O
Molar mass 212.25 g/mol
Density 1.326 g/cm3
Melting point 321 °C (610 °F; 594 K) (·HCl); 262 °C (·HCl·2H2O)[2]
insoluble[1]
Solubility in Dimethyl sulfoxide 100mM[1]
Solubility in Ethanol 1 mg/mL[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Harmine is a beta-carboline and a harmala alkaloid. It occurs in a number of different plants, most notably the Syrian rue and Banisteriopsis caapi.[3] Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a Reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B.[4] Harmine is also known as banisterin, banisterine, telopathin, telepathine, leucoharmine[5] and yagin, yageine.[3][6]

  1. ^ a b c "Harmine - CAS 442-51-3". scbio.de. Santa Cruz Biotechnology, Inc. Retrieved 27 October 2015.
  2. ^ The Merck Index (1996). 12th edition
  3. ^ a b Djamshidian A, et al. (2015). "Banisteriopsis caapi, a Forgotten Potential Therapy for Parkinson's Disease?". Movement Disorders Clinical Practice. 3 (1): 19–26. doi:10.1002/mdc3.12242. PMC 6353393. PMID 30713897.
  4. ^ Frecska E, Bokor P, Winkelman M (2016). "The Therapeutic Potentials of Ayahuasca: Possible Effects against Various Diseases of Civilization". Frontiers in Pharmacology. 7: 35. doi:10.3389/fphar.2016.00035. PMC 4773875. PMID 26973523.
  5. ^ Allen JR, Holmstedt BR (1980). "The simple β-carboline alkaloids". Phytochemistry. 19 (8): 1573–1582. Bibcode:1980PChem..19.1573A. doi:10.1016/S0031-9422(00)83773-5.
  6. ^ "SciFinderⁿ Login". sso.cas.org. Retrieved 2021-11-12.