Vasicin

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Vasicin
other names	Peganine; 1,2,3,9-Tetrahydropyrrolo- [2,1- b ] quinazolin-3-ol;
Molecular formula	C 11 H 12 N 2 O
Brief description	colorless solid
External identifiers / databases
PubChem	72610
ChemSpider	65485
Wikidata	Q15427948
properties
Molar mass	188.23 g · mol -1
Physical state	firmly
Melting point	211-212 ° C [(-) - ( R ) -Vasicine]
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vasicin (synonym: peganin ) is a chemical compound that belongs to the heterocycles and is derived from quinazoline . Vasicin belongs to the group of quinazoline alkaloids .

The origin of the name is traced back to the occurrence in the Indian lungwort ( Justicia adhatoda L. , synonym: Adhatoda vasica Nees , also called Vasica).

Occurrence

Rue ( Peganum harmala )

(-) - ( R ) -Vasicine could be isolated from steppe rue ( Peganum harmala ), Linaria species and the goat's rue ( Galega officinalis ). It often occurs with the accompanying alkaloids vasicinone and desoxyvasicinone .

The racemate also occurs naturally in Anisotes sessiliflorus .

biosynthesis

It seems certain that one of the biosynthetic building blocks of vasicin and the structurally related alkaloids is anthranilic acid . The other starting materials are unknown.

properties

Vasicin easily racemizes in acidic solution and when heated.

effect

Phytopreparations with vasicin were already used as expectorants and secretolytics in Indian folk medicine .

Vasicine is a stimulant of breathing and acts bronchodilator . It served as a lead structure for the pharmacological development of secretolytically active substances such as ambroxol or bromhexine .

Individual evidence

↑ ^a ^b ^c data sheet Vasicine at Sigma-Aldrich , accessed on March 24, 2016 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f Entry on peganine. In: Römpp Online . Georg Thieme Verlag, accessed on March 24, 2016.
↑ External identifiers of or database links to (-) - Vasicin : CAS number: 6159-55-3, EC number: 228-180-8, ECHA InfoCard: 100.025.619 , PubChem : 667496 , ChemSpider : 580873 , Wikidata : Q27264469 .

[Sigma-1] ta sheet Vasicine at Sigma-Aldrich , accessed on March 24, 2016 ( PDF ).

[Römpp-2] ↑ ^a ^b ^c ^d ^e ^f Entry on peganine. In: Römpp Online . Georg Thieme Verlag, accessed on March 24, 2016.

[3] External identifiers of or database links to (-) - Vasicin : CAS number: 6159-55-3, EC number: 228-180-8, ECHA InfoCard: 100.025.619 , PubChem : 667496 , ChemSpider : 580873 , Wikidata : Q27264469 .