Vasicine

Base Information

• Chemical Name: Vasicine
• CAS No.: 6159-55-3
• Deprecated CAS: 89-70-3
• Molecular Formula: C11H12 N2 O
• Molecular Weight: 188.229
• Hs Code.: 2933990090
• European Community (EC) Number: 228-180-8
• UNII: 6C2ZBI733P
• DSSTox Substance ID: DTXSID601024261
• Nikkaji Number: J1.032.961B
• Wikipedia: Vasicine
• Wikidata: Q27264469
• ChEMBL ID: CHEMBL2163791
• Mol file: 6159-55-3.mol

Synonyms:peganine;peganine hydrochloride dihydrate;vasicine;vasicine hydrochloride, (R)-isomer;vasicine monohydrochloride, (R)-isomer;vasicine, (+-)-isomer

Chemical Property of Vasicine

Chemical Property:

• Vapor Pressure: 2.98E-06mmHg at 25°C
• Melting Point: 182 ºC
• Refractive Index: 1.709
• Boiling Point: 373.8 °C at 760 mmHg
• PKA: 13.08±0.20(Predicted)
• Flash Point: 179.9 °C
• PSA: 35.83000
• Density: 1.37 g/cm³
• LogP: 0.67030
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 188.094963011
• Heavy Atom Count: 14
• Complexity: 264

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,2,3,9-tetrahydropyrrolo[2,1-b]quinazolin-3-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC3=CC=CC=C3N=C2C1O
• Isomeric SMILES: C1CN2CC3=CC=CC=C3N=C2[C@H]1O
• 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.

Technology Process of Vasicine

There total 2 articles about Vasicine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

vasicine (6159-56-4,176200-11-6) → vasicine (18549-38-7) + (+)-vasicinol (6159-55-3)

Guidance literature:

With 2,2'-iminobis[ethanol]; In ethanol; Resolution of racemate;

DOI:10.1016/j.ejps.2018.07.058

Reference yield:

vasicine (6159-56-4,176200-11-6) → (+)-vasicinol (6159-55-3)

Guidance literature:

With D-tartaric acid;

Reference yield: 99.0%

(+)-vasicinol (6159-55-3) → (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol (1227263-77-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; water; for 2h; Solvent;

DOI:10.1002/hlca.201200307

upstream raw materials:

vasicine

Downstream raw materials:

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol

(R)-N-benzyl-3-hydroxypyrrolidine

(S)-N-benzyl-3-hydroxypyrrolidine

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate

Refernces