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Nicergoline

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Nicergoline Basic information

Product Name:
Nicergoline
CAS:
27848-84-6
MF:
C24H26BrN3O3
MW:
484.39
EINECS:
248-694-6
Mol File:
27848-84-6.mol
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Nicergoline Chemical Properties

Melting point:
136-138°
Boiling point:
594.4±50.0 °C(Predicted)
Density 
1.3558 (rough estimate)
refractive index 
1.6200 (estimate)
storage temp. 
2-8°C
solubility 
Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent).
form 
neat
pka
6.33±0.40(Predicted)
Water Solubility 
Soluble in alcohol, chloroform, and acetone. Insoluble in water.
Merck 
14,9496
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
36
RIDADR 
1544
WGK Germany 
3
RTECS 
KE6341000
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29396100
Toxicity
LD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner)

MSDS

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Nicergoline Usage And Synthesis

Chemical Properties

Fine to granular, white or yellowish powder.

Originator

Sermion,Farmitalia,Italy,1974

Uses

antipsychotic

Manufacturing Process

Preparation of 1-Methyl Lumilysergic Acid 8-Methyl Ester-10-Methyl Ether: Into a suspension of 10 grams of 1-methyl-lumilysergic acid in 600 cc of absolute methanol a stream of anhydrous hydrogen chloride is bubbled for 1.5 hours with strong cooling. The stream of hydrogen chloride is stopped and the mixture is allowed to stand for 30 minutes at 0°C, and is evaporated in vacuo to dryness. The residue is taken up with ice-cooled water made alkaline with concentrated ammonia and extracted with chloroform. The combined chloroform extracts are washed first with a 5% aqueous solution of sodium bicarbonate, then with water, and are thereafter dried over anhydrous sodium sulfate and finally evaporated in vacuo to dryness.
Preparation of 1-Methyl Lumilysergol-10-Methyl Ether: To a boiling suspension of 2 grams of lithium aluminum hydride in 50 cc of anhydrous tetrahydrofuran, a solution of 1 gram of 1-methyl lumilysergic acid-8-methyl ester-10-methyl ether in 20 cc of anhydrous tetrahydrofuran is added dropwise and the resulting solution is refluxed for a further 2 hours. After cooling the resulting solution, aqueous tetrahydrofuran is added to destroy the excess reducing agent and the solution is filtered. Tetrahydrofuran is distilled off and the residue is recrystallized from acetone petroleum ether.
Preparation of Nicergoline: To a solution of 1-methyl lumilysergol-10-methyl ether in pyridine, 5-bromonicotinyl chloride is used as an acylating agent at room temperature. The mixture is stirred for 1 hour. Water and methanol are added and the resulting mixture is stirred for 1 hour, extracted with chloroform, and washed in sequence with 1% aqueous caustic soda, 5% aqueous sodium bicarbonate solution, and water. The resulting solution is dried over anhydrous sodium sulfate and the solvent is distilled off. By recrystallization of the residue from acetone petroleum ether, nicergoline is obtained, melting at 136° to 138°C.

brand name

Sermion (Farmitalia, Societa Farmaceutici Italia, Italy).

Therapeutic Function

Vasodilator

Biological Activity

α -adrenergic, vasodilator. Cognitive enhancer.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Other experimental reproductive effects. A vasodilator. When heated to decomposition it emits very toxic fumes of Brand NOx.

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NicergolineSupplierMore

Hubei widely chemical technology Co., Ltd. Gold
Tel:
13419635609 027-59402396-
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13419635609@163.com
J & K SCIENTIFIC LTD.
Tel:
400-666-7788 010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
400-660-8290 21-61259100-
Email:
sh@meryer.com
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel:
18930552037 821-50328103-801
Email:
3bsc@sina.com
TCI (Shanghai) Development Co., Ltd.
Tel:
021-67121386 / 800-988-0390
Email:
Sales-CN@TCIchemicals.com
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