Harmaline

Structural formula
General
Surname	Harmaline
other names	4,9-dihydro-7-methoxy-1-methyl-3 H -pyrido [3,4- b ] indole; 4,9-dihydro-7-methoxy-1-methyl-3 H -β-carboline;
Molecular formula	C 13 H 14 N 2 O
Brief description	beige solid
External identifiers / databases
EC number	206-152-6
ECHA InfoCard	100.005.594
PubChem	5280951
ChemSpider	10211258
Wikidata	Q135270
properties
Molar mass	214.26 g mol −1 ; 286.75 g mol −1 (hydrochloride dihydrate);
Physical state	firmly
Melting point	232-234 ° C
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Harmalin is a psychoactive indole alkaloid from the group of Harman alkaloids . It is the reduced ( hydrogenated ) form of harmine .

history

In 1841 harmaline was from the Syrian rue isolated from Goegel. In 1919 Perkin Jr. (son of WH Perkin ) and Robinson proposed a structure, which was underpinned in 1927 by the first synthesis of Manske, Perkin and Robinson. In the same year Hasenfratz published an improved extraction method for harmaline.

Occurrence

Rue ( Peganum harmala )

Harmaline and harmine under UV light

The plants Banisteriopsis caapi (a jungle tendril) and Peganum harmala ( rue ) as well as Ayahuasca contain harmaline.

effect

Harmaline has a oneirogenic effect ( dream-generating ) and causes ataxia . It differs significantly from hallucinogens in its pharmacology . Harmalin is a reversible monoamine oxidase inhibitor and can sometimes enormously or uncontrollably increase the effect of some drugs. Harmaline does not create physical or psychological dependence .

Web links

Harmaline and harmine . In: Erowid . (English)
TIHKAL, # 13 (English)

Individual evidence

↑ ^a ^b ^c data sheet Harmaline at Sigma-Aldrich , accessed on December 22, 2013 ( PDF ).
↑ Lotsof, HS "Method of treating chemical dependency using β-carboline alkaloids, derivatives and salts thereof" United States Patent US5591738 1997 .
↑ Perkin, WH, Jr .; Robinson, R. "LXXIX. Harmine and harmaline. Part III." Journal of the Chemical Society , Transactions 1919 , 115 , 933-967.
↑ Perkin, WH, Jr .; Robinson, R. "LXXX. Harmine and harmaline. Part IV." Journal of the Chemical Society, Transactions 1919 , 115 , 967-972.
↑ Manske, RHF; Perkin, WH, Jr .; Robinson, R. "Harmine and Harmaline. Part IX. A Synthesis of Harmaline." Journal of the Chemical Society 1927 , 1-14.
↑ Hasenfratz, V. "Harmaline and harmine." Annali di Chimica Applicata 1927 , 7 , 151-226.

[Aldrich-1] ta sheet Harmaline at Sigma-Aldrich , accessed on December 22, 2013 ( PDF ).

[fpo-2] Lotsof, HS "Method of treating chemical dependency using β-carboline alkaloids, derivatives and salts thereof" United States Patent US5591738 1997 .

[perkin1-3] Perkin, WH, Jr .; Robinson, R. "LXXIX. Harmine and harmaline. Part III." Journal of the Chemical Society , Transactions 1919 , 115 , 933-967.

[perkin2-4] Perkin, WH, Jr .; Robinson, R. "LXXX. Harmine and harmaline. Part IV." Journal of the Chemical Society, Transactions 1919 , 115 , 967-972.

[manske-5] Manske, RHF; Perkin, WH, Jr .; Robinson, R. "Harmine and Harmaline. Part IX. A Synthesis of Harmaline." Journal of the Chemical Society 1927 , 1-14.

[hasenfratz-6] Hasenfratz, V. "Harmaline and harmine." Annali di Chimica Applicata 1927 , 7 , 151-226.