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Vasicine

Vasicine Structure
CAS No.
6159-55-3
Chemical Name:
Vasicine
Synonyms
PEGANINE;1,2,3,9-TETRAHYDROPYRROLO[2,1-B]QUINAZOLIN-3-OL;C10733;vasicin;VASICINE;ST012797;TOS-BB-0711;NCI60_030781;(-)-Vasicine;AKOS NCG1-0080
CBNumber:
CB5300633
Molecular Formula:
C11H12N2O
Molecular Weight:
188.23
MOL File:
6159-55-3.mol
MSDS File:
SDS
Modify Date:
2024/4/1 18:08:31

Vasicine Properties

Melting point 211.5°C
Boiling point 323.23°C (rough estimate)
Density 1.1124 (rough estimate)
refractive index 1.5850 (estimate)
solubility DMSO : 83.33 mg/mL (442.70 mM; Need ultrasonic)
form Powder
pka 13.08±0.20(Predicted)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xn
Risk Statements  22
RIDADR  1544
HazardClass  6.1(b)
PackingGroup  III

Vasicine Chemical Properties,Uses,Production

Description

This quinazoline alkaloid was first isolated from the leaves of Adhatoda vasica Nees by Hooper and subsequently discovered in Peganum harmala under the name Peganine. The base is optically inactive although Spath and Kesztler have reported the isolation of the (-)-form from the fresh leaves of A. vasica and Rosenfeld and Kolesnikow have obtained the same form from the flowers and stems of Peganum harmala. The salts are readily obtained crystalline, e.g. the hydrochloride dihydrate, m.p. 208°C (dry); hydriodide dihydrate, m.p. 195°C (dry); picrate, m.p. 199°C (dec.) and the methiodide, m.p. 187°C.
With AcOH, the alkaloid gives an anomalous acetyl derivative, m.p. 165°C, subsequently shown to be N-acetylpedadiene. Oxidation with KMn04 gives 4-quinazolone and 4-keto-3 :4-dihydroxyquinazolyl-3-acetic acid, the latter characterized as the methyl ester, m.p. 152°C.
The crude drug from A. vasica is used in India as a remedy for asthma while the pure alkaloid acts as a bronchodilator.

Chemical Properties

White needle-like crystals, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from camels.

Biological Activity

Vasicine, isolated from A. vasica, is an alkaloid. It is a natural cholinesterase (cholinesterase) inhibitor, has anticholinesterase activity in preclinical models, and can be used for the development of therapeutic drugs for Alzheimer's disease.

References

Hooper., Pharm. J., 18,841 (1888)
Sen, Ghose.,J. Ind. Chem. Soc., 1,315 (1924)
Ghose., ibid, 4, 1 (1927)
Spath, Nakawitz., Ber., 67,45 (1934)
Spath, Kuffner., ibid, 67, 1494 (1934)
Narang, Ray., Chem. & Ind., 53,698 (1934)
Hanford, Liang, Adams., J. Amer. Chem. Soc., 56, 2780 (1934)
Ghoseetal., ibid, 57,921,951 (1935)
Rosenfeld, Kolesnikov., Ber., 69, 2022 (1936)
Pharmacology: Chopra., Ind. Med. Gaz., 60, 354 (1925)
Tutaev, Makarova., Trans. Ukraine Inst. Exp. Pharm., 1,32 (1938)

Vasicine Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 118)Suppliers
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CHEMAZON LABORATORIES +91 9848551964 Hyderabad, India 1320 58 Inquiry
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AFINE CHEMICALS LIMITED +86-0571-85134551 China 15395 58 Inquiry
TargetMol Chemicals Inc. +1-781-999-5354 United States 19973 58 Inquiry
1-b)quinazolin-3-ol,1,2,3,9-tetrahydro-pyrrolo( vasicin AKOS NCG1-0080 VITAS-BB TBB000541 VASICINE C10733 HARMALINE HCL(RG) (3R)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol 1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazoline-3β-ol (R)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol Pyrrolo[2,1-b]quinazolin-3-ol,1,2,3,9-tetrahydro-, (3S)- (3S)-1,2,3,9-Tetrahydropyrrolo[2,1-b]quinazolin-3-ol NCI60_030781 ST012797 TOS-BB-0711 Ductile alkaloids VASICINE USP/EP/BP Vasicine(Secondary Standards traceble to USP) 1,2,3,9-TETRAHYDROPYRROLO[2,1-B]QUINAZOLIN-3-OL PEGANINE (-)-Vasicine 6159-55-3 Miscellaneous Natural Products Alkaloids