Bulbocapnin

Structural formula
	Structural formula of ( S ) - (+) - bulbocapnine
General
Surname	Bulbocapnin
Molecular formula	C 19 H 19 NO 4
Brief description	rhombic prisms
External identifiers / databases
EC number	206-061-1
ECHA InfoCard	100.005.511
PubChem	12441
ChemSpider	11934
Wikidata	Q1003526
properties
Molar mass	325.36 g · mol -1
Physical state	firmly
Melting point	213-214 ° C [( RS ) -Bulbocapnin] ; 202–203 ° C [( R ) - (-) - bulbocapnine] ; 201-203 ° C [( S ) - (+) - Bulbocapnin] ;
solubility	soluble in ethanol , chloroform and diethyl ether
safety instructions
GHS labeling of hazardous substances Hydrochloride Caution
H and P phrases	H: 302-332
	P: 261-312-304 + 340
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bulbocapnine is an aporphine alkaloid; it is structurally similar to apomorphine .

Occurrence

Bleeding heart ( Dicentra spectabilis )

It occurs in plants of the species Larkspurne and Bleeding Heart as well as other herbs of the Erdrauchgewächse family .

Physiological effect

Bulbocapnin can cause fatal poisoning in sheep and cattle .

According to the Dorlands Medical Dictionary , it inhibits the activity of the striated muscles in humans. It is used to treat muscular tremor and vestibular nystagmus . Psychiatrist Robert Heath carried out tests on inmates in one of the largest prisons in the United States in order to sedate them with the substance. Author William S. Burroughs incorporates this plot into his book Naked Lunch , in which the fictional Dr. Benway uses it to make victims of torture obedient.

literature

Hisashi Asakawa: About the influence of the so-called extrapyramidal poisons, bulbocapnine, harmine and harmaline on the glutathione content of the liver, spleen and blood of rabbits . In: Acta Medica Okayama . tape 6 , no. June 2 , 1939 ( okayama-u.ac.jp [PDF]).

Individual evidence

↑ FK Beilstein: Handbook of Organic Chemistry . S. 877 ( limited preview in Google Book search).
↑ ^a ^b ^c The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 243, ISBN 978-0-911910-00-1 .
^ Ernst Albert Schmidt: Detailed textbook of pharmaceutical chemistry . F. Vieweg, 1911, p. 762 ( PDF ).
↑ ^a ^b biosynth.com: Bulbocapnine hydrochloride , accessed on May 16, 2017.
↑ Entry on aporphine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.
↑ Bulbocapnine. In: ChEBI. European Bioinformatics Institute , accessed on May 26, 2017 .

[F._K._Beilstein-1] FK Beilstein: Handbook of Organic Chemistry . S. 877 ( limited preview in Google Book search).

[MerckIndex-2] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, p. 243, ISBN 978-0-911910-00-1 .

[Ernst_Albert_Schmidt-3] Ernst Albert Schmidt: Detailed textbook of pharmaceutical chemistry . F. Vieweg, 1911, p. 762 ( PDF ).

[biosynth.com-4] synth.com: Bulbocapnine hydrochloride , accessed on May 16, 2017.

[5] Entry on aporphine alkaloids. In: Römpp Online . Georg Thieme Verlag, accessed on June 7, 2014.

[6] Bulbocapnine. In: ChEBI. European Bioinformatics Institute , accessed on May 26, 2017 .