Harmalol

Structural formula
General
Surname	Harmalol
other names	1-methyl-3 H , 4 H , 9 H -pyrido [3,4- b ] indol-7-ol ( IUPAC ) ; 4,9-dihydro-1-methyl-3 H -pyrido [3,4- b ] indol-7-ol; 3,4-dihydro-7-hydroxy-1-methyl-β-carboline; Harmidol; Harmolol;
Molecular formula	C 12 H 12 N 2 O
Brief description	yellow solid (base and hydrochloride dihydrate)
External identifiers / databases
EC number	208-375-4
ECHA InfoCard	100.007.616
PubChem	5353656
ChemSpider	4510170
Wikidata	Q15138221
properties
Molar mass	200.24 g mol −1 (base); 272.73 g mol −1 (hydrochloride dihydrate); 236.7 g mol −1 (hydrochloride);
Physical state	firmly
Melting point	212 ° C (base); 264–267 ° C (decomposition) (hydrochloride dihydrate); 260–267 ° C (hydrochloride);
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Harmalol is an indole alkaloid that belongs to the group of substances consisting of β-carbolines and harmane alkaloids .

Occurrence

Ayahuasca

It occurs in Ayahuasca , in the stems of Passiflora incarnata and Hippophae rhamnoides , in the roots of Apocynum cannabinum , and in the seeds of the rue ( Peganum harmala ).

Physiological effect

Harmalol is a monoamine oxidase and butyrylcholinesterase inhibitor. It also inhibits the cancer-activating enzyme CYP1A1 . It is used in DNA or RNA alkaloid binding studies. Harmalol increased pulse amplitude , maximal aortic flow, and cardiac muscle contraction in anesthetized dogs with normal blood pressure.

Individual evidence

↑ sigmaaldrich.com: Product Specification Harmalol Hydrochloride Dihydrate (PDF; 18 kB), accessed on November 7, 2013.
^ RHF Manske (Ed.): The Alkaloids: Chemistry and Physiology . tape 8 . Academic Press, New York 1965, ISBN 978-0-08-086532-4 , pp. 49 ( limited preview in Google Book search).
↑ Data sheet Harmalol hydrochloride dihydrate from Sigma-Aldrich , accessed on November 7, 2013 ( PDF ).
↑ MP Biomedicals: Safety data sheet HARMALOL HYDROCHLORIDE (PDF; 22 kB), accessed on November 7, 2013.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Metabocard for Harmalol (HMDB29838)
↑ ^a ^b Ting Zhao, Ke-min Ding, Lei Zhang, Xue-mei Cheng, Chang-hong Wang, Zheng-tao Wang: Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activities of β-Carboline and Quinoline Alkaloids Derivatives from the Plants of Genus Peganum. In: Journal of Chemistry. 2013, 2013, pp. 1–6, doi: 10.1155 / 2013/717232 .
↑ EH McIlhenny, KE Pipkin, LJ Standish, HA Wechkin, R. Strassman, SA Barker: Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography-electrospray ionization-tandem mass spectrometry. In: Journal of chromatography. A. Volume 1216, number 51, December 2009, pp. 8960-8968, doi: 10.1016 / j.chroma.2009.10.088 . PMID 19926090 .
↑ Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.
↑ List, PH and Horhammer, L .: Hager's Handbook of Pharmaceutical Practice , Vols. 2–6, Springer Verlag, Berlin, 1969–1979.
↑ Data sheet Harmalol hydrochloride dihydrate from Sigma-Aldrich , accessed on November 7, 2013 ( PDF ).
↑ MA El Gendy, AA Soshilov, MS Denison, AO El-Kadi: Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms. In: Food and Chemical Toxicology . Volume 50, number 2, February 2012, pp. 353-362, doi: 10.1016 / j.fct.2011.10.052 . PMID 22037238 . PMC 3281145 (free full text).
^ S. Nafisi, ZM Malekabady, MA Khalilzadeh: Interaction of β-carboline alkaloids with RNA. In: DNA and cell biology. Volume 29, number 12, December 2010, pp. 753-761, doi: 10.1089 / dna.2010.1087 . PMID 20731607 .
↑ S. Nafisi, M. Bonsaii, P. Maali, MA Khalilzadeh, F. Manouchehri: Beta-carboline alkaloids bind DNA. In: Journal of photochemistry and photobiology. B, Biology. Volume 100, number 2, August 2010, pp. 84-91, doi: 10.1016 / j.jphotobiol.2010.05.005 . PMID 20541950 .
↑ Darbyl H. Aarons, G. Victor Rossi, Raymond F. Orzechowski: Cardiovascular actions of three harmala alkaloids: Harmine, harmaline, and harmalol. In: Journal of Pharmaceutical Sciences . 66, 1977, pp. 1244-1248, doi: 10.1002 / jps.2600660910 .

[1] sigmaaldrich.com: Product Specification Harmalol Hydrochloride Dihydrate (PDF; 18 kB), accessed on November 7, 2013.

[2] RHF Manske (Ed.): The Alkaloids: Chemistry and Physiology . tape 8 . Academic Press, New York 1965, ISBN 978-0-08-086532-4 , pp. 49 ( limited preview in Google Book search).

[sigma-3] Data sheet Harmalol hydrochloride dihydrate from Sigma-Aldrich , accessed on November 7, 2013 ( PDF ).

[mp-4] MP Biomedicals: Safety data sheet HARMALOL HYDROCHLORIDE (PDF; 22 kB), accessed on November 7, 2013.

[NV-5] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[6] Metabocard for Harmalol (HMDB29838)

[DOI10.1155/2013/717232-7] Ting Zhao, Ke-min Ding, Lei Zhang, Xue-mei Cheng, Chang-hong Wang, Zheng-tao Wang: Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activities of β-Carboline and Quinoline Alkaloids Derivatives from the Plants of Genus Peganum. In: Journal of Chemistry. 2013, 2013, pp. 1–6, doi: 10.1155 / 2013/717232 .

[PMID19926090-8] EH McIlhenny, KE Pipkin, LJ Standish, HA Wechkin, R. Strassman, SA Barker: Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography-electrospray ionization-tandem mass spectrometry. In: Journal of chromatography. A. Volume 1216, number 51, December 2009, pp. 8960-8968, doi: 10.1016 / j.chroma.2009.10.088 . PMID 19926090 .

[9] Duke, James A. 1992. Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.

[10] List, PH and Horhammer, L .: Hager's Handbook of Pharmaceutical Practice , Vols. 2–6, Springer Verlag, Berlin, 1969–1979.

[11] Data sheet Harmalol hydrochloride dihydrate from Sigma-Aldrich , accessed on November 7, 2013 ( PDF ).

[PMID22037238-12] MA El Gendy, AA Soshilov, MS Denison, AO El-Kadi: Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms. In: Food and Chemical Toxicology . Volume 50, number 2, February 2012, pp. 353-362, doi: 10.1016 / j.fct.2011.10.052 . PMID 22037238 . PMC 3281145 (free full text).

[PMID20731607-13] S. Nafisi, ZM Malekabady, MA Khalilzadeh: Interaction of β-carboline alkaloids with RNA. In: DNA and cell biology. Volume 29, number 12, December 2010, pp. 753-761, doi: 10.1089 / dna.2010.1087 . PMID 20731607 .

[PMID20541950-14] S. Nafisi, M. Bonsaii, P. Maali, MA Khalilzadeh, F. Manouchehri: Beta-carboline alkaloids bind DNA. In: Journal of photochemistry and photobiology. B, Biology. Volume 100, number 2, August 2010, pp. 84-91, doi: 10.1016 / j.jphotobiol.2010.05.005 . PMID 20541950 .

[DOI10.1002/jps.2600660910-15] Darbyl H. Aarons, G. Victor Rossi, Raymond F. Orzechowski: Cardiovascular actions of three harmala alkaloids: Harmine, harmaline, and harmalol. In: Journal of Pharmaceutical Sciences . 66, 1977, pp. 1244-1248, doi: 10.1002 / jps.2600660910 .