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HomeProduct name listNicergoline

Nicergoline

Synonym(s):5-Bromonicotinic acid 10-methoxy-1,6-dimethylergoline-8-methyl ester;Nicergoline

  • CAS NO.:27848-84-6
  • Empirical Formula: C24H26BrN3O3
  • Molecular Weight: 484.39
  • MDL number: MFCD00869626
  • EINECS: 248-694-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-21 17:11:28
Nicergoline Structural

What is Nicergoline?

Chemical properties

Fine to granular, white or yellowish powder.

Originator

Sermion,Farmitalia,Italy,1974

The Uses of Nicergoline

Nicergoline is a drug used for age-dependent cognitive impairment such as Alzheimers disease and other types of dementia. Nicergoline has shown to protect cultured neurons against β-amyloid toxicity. Nicergoline protects against neuronal cell death induced by activated microglia and astrocytes through the inhibition of inflammatory mediators and the upregulation of neurotrophic factors by glial cells. Nicergoline is a drug used for age-dependent cognitive impairment and it protects cultured neurons against β-amyloid toxicity.

The Uses of Nicergoline

antipsychotic

Indications

For the treatment of senile dementia, migraines of vascular origin, transient ischemia, platelet hyper-aggregability, and macular degeneration.

Background

An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It has been suggested to ameliorate cognitive deficits in cerebrovascular disease.

What are the applications of Application

Nicergoline is an α-adrenergic modulator and vasodilator

Definition

ChEBI: Nicergoline is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.

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.

Pharmacokinetics

Nicergoline is a potent vasodilator (improves brain blood flow). On the cerebral level it prompts a lowering of vascular resistance, an increase in arterial flow and stimulates the use of oxygen and glucose. Nicergoline also improves blood circulation in the lungs and limbs and has been shown to inhibit blood platelet aggregation.

Pharmacology

Nicergoline is an ergot derivative that may protect against degeneration of cholinergic neurones (Giardino et al.,2002). Nicergoline has a broad spectrum of action (Winblad et al,2008): (1) as a1-adrenoceptor antagonist it induces vasodilatation and increases arterial blood flow; (2) it enhances cholinergic and catecholaminergic neurotransmission; (3) it inhibits platelet aggregation; (4) it promotes metabolic activity, resulting in increased oxygen and glucose utilization; and (5) it has neurotrophic and antioxidant properties. Nicergoline has been used for the treatment of various dementias, including AD and VaD (Fioravanti and Flicker, 2001). The therapeutic effects of nicergoline were evident by 2 months of treatment and were maintained for 6-12 months.

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.

Metabolism

Properties of Nicergoline

Melting point: 136-138°
Boiling point: 594.4±50.0 °C(Predicted)
Density  1.3558 (rough estimate)
refractive index  1.6200 (estimate)
storage temp.  Keep in dark place,Inert atmosphere,Store in freezer, under -20°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)
form  Solid
color  White to Off-White
Water Solubility  Soluble in alcohol, chloroform, and acetone. Insoluble in water.
Merck  14,9496

Safety information for Nicergoline

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral

Computed Descriptors for Nicergoline

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