Harmine

Structural formula
General
Surname	Harmine
other names	7-methoxy-1-methyl-9 H -pyrido [3,4- b ] indole; Telepath; Banisteress; Yagein;
Molecular formula	C 13 H 12 N 2 O
Brief description	beige solid
External identifiers / databases
EC number	207-131-4
ECHA InfoCard	100.006.485
PubChem	5280953
ChemSpider	4444445
DrugBank	DB07919
Wikidata	Q128381
properties
Molar mass	212.25 g · mol -1 ; 248.71 g · mol -1 (· harmine hydrochloride) ;
Physical state	firmly
Melting point	261 ° C ; 321 ° C (harmine hydrochloride ) ;
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-312-319-332
	P: 280-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Harmine is an alkaloid from the group of Harman alkaloids and thus also the β-carbolines . In the human body it acts as a reversible MAO inhibitor ( monoamine oxidase inhibitor ), stimulating the central nervous system. The enzyme MAO-A is blocked here, but not the similarly acting MAO-B.

properties

In its pure form, harmine forms yellowish, brittle, shiny and strongly refractive crystals that consist of rhombic prisms. Long crystal needles form when precipitating in the heat, whereas larger single crystals form when slowly crystallizing. The substance does not dissolve much in cold water or ethanol , better in ether , basic or hot water. By reducing forms of harmine harmaline .

use

As an MAO inhibitor, harmine prevents the breakdown of monoamines by the enzyme monoamine oxidase. So it delays u. a. the metabolism of the neurotransmitters serotonin and dopamine , the hormone melatonin and various psychedelic hallucinogens based on tryptamine, such as DMT , psilocybin / psilocin , and the phenylethylamine mescaline . Harmine is currently not used as an antidepressant because other MAOIs are known to have fewer side effects. In doses of 150 mg or more, harmine can cause vomiting, diarrhea and tremors.

In contrast, harmine plays a crucial role in the preparation of the traditional South American entheogen Ayahuasca . It is only through its function as an MAO inhibitor that the breakdown of the DMT, which is also contained in the potion, is delayed to such an extent that it can also work when taken orally.

Harmine is also used as a fluorescent pH indicator. Its fluorescence decreases with increasing pH.

Occurrence

Harmine occurs in numerous plants, including the steppe rue ( Peganum harmala ), which gave harmine and harmalin its name. The liana Banisteriopsis caapi used for the ayahuasca mentioned above also contains harmine. In addition to plants, the alkaloid is also found in other organisms.

Shulgin (1997) lists around 30 different species whose metabolism produces harmine, for example seven butterfly species from the noble butterfly family .

Web links

Harmaline and harmine . In: Erowid . (English)
TIHKAL, # 14 (English)

Individual evidence

↑ ^a ^b ^c R. Hansel, K. Keller, H. Rimpler, G. Schneider (Eds.): Hager's Handbook of Pharmaceutical Practice: Volume 4: "Drugs AD" , p. 458, Springer Berlin 1992, ISBN 978-3 -642-63468-0 doi : 10.1007 / 978-3-642-58087-1_2
↑ ^a ^b ^c Data sheet Harmine at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).
↑ ^a ^b The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 798, ISBN 978-0-911910-00-1 .
↑ Abstract Gerardy J, "Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline.", Department of Pharmacology, University of Liège, Sart Tilman, Belgium ( Memento of the original from May 26, 2011 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . @1@ 2

↑ OL Erdmann: Journal for practical chemistry , pp. 275-290, 1847, Johann Ambrosius Barth Verlag, Leipzig.

↑ Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. P. 713f.

[hagers-1] R. Hansel, K. Keller, H. Rimpler, G. Schneider (Eds.): Hager's Handbook of Pharmaceutical Practice: Volume 4: "Drugs AD" , p. 458, Springer Berlin 1992, ISBN 978-3 -642-63468-0 doi : 10.1007 / 978-3-642-58087-1_2

[Sigma-2] Data sheet Harmine at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).

[MerckIndex-3] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 798, ISBN 978-0-911910-00-1 .

[4] Abstract Gerardy J, "Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline.", Department of Pharmacology, University of Liège, Sart Tilman, Belgium ( Memento of the original from May 26, 2011 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . @1@ 2

[5] OL Erdmann: Journal for practical chemistry , pp. 275-290, 1847, Johann Ambrosius Barth Verlag, Leipzig.

[6] Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. P. 713f.