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Nicergoline

CAS No.
27848-84-6
Chemical Name:
Nicergoline
Synonyms
mne;Memoq;fi6714;TA 079;Ergotop;Sermion;Ergobel;CS-1354;Cergodum;nargoline
CBNumber:
CB9728301
Molecular Formula:
C24H26BrN3O3
Molecular Weight:
484.39
MDL Number:
MFCD00869626
MOL File:
27848-84-6.mol
MSDS File:
SDS
Last updated:2024-11-13 18:13:23

Nicergoline 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. 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 Solid
pka 6.33±0.40(Predicted)
color White to Off-White
Water Solubility Soluble in alcohol, chloroform, and acetone. Insoluble in water.
Merck 14,9496
FDA UNII JCV8365FWN
ATC code C04AE02

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
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)
NFPA 704
0
1 0

Nicergoline price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich Y0001352 Nicergoline for system suitability European Pharmacopoeia (EP) Reference Standard 27848-84-6 y0001352 $150 2024-03-01 Buy
Sigma-Aldrich N7889 Nicergoline analytical standard, for drug analysis 27848-84-6 100mg $44.1 2024-03-01 Buy
TCI Chemical N0904 Nicergoline >98.0%(HPLC)(T) 27848-84-6 100mg $37 2024-03-01 Buy
TCI Chemical N0904 Nicergoline >98.0%(HPLC)(T) 27848-84-6 1g $221 2024-03-01 Buy
Alfa Aesar J63295 Nicergoline 27848-84-6 100mg $80.65 2024-03-01 Buy
Product number Packaging Price Buy
Y0001352 y0001352 $150 Buy
N7889 100mg $44.1 Buy
N0904 100mg $37 Buy
N0904 1g $221 Buy
J63295 100mg $80.65 Buy

Nicergoline Chemical Properties,Uses,Production

Chemical Properties

Fine to granular, white or yellowish powder.

Originator

Sermion,Farmitalia,Italy,1974

Uses

antipsychotic

Uses

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.

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.

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.

Nicergoline Preparation Products And Raw materials

Raw materials

Preparation Products

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Related articles

View Lastest Price from Nicergoline manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Nicergoline pictures 2024-11-14 Nicergoline
27848-84-6
US $0.00 / KG 1KG 99%min 10kg WUHAN FORTUNA CHEMICAL CO., LTD
Nicergoline pictures 2024-11-13 Nicergoline
27848-84-6
US $30.00-62.00 / mg 99.53% 10g TargetMol Chemicals Inc.
Nicergoline pictures 2024-11-13 Nicergoline
27848-84-6
US $30.00-62.00 / mg 99.53% 10g TargetMol Chemicals Inc.
  • Nicergoline pictures
  • Nicergoline
    27848-84-6
  • US $0.00 / KG
  • 99%min
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Nicergoline pictures
  • Nicergoline
    27848-84-6
  • US $30.00-62.00 / mg
  • 99.53%
  • TargetMol Chemicals Inc.
  • Nicergoline pictures
  • Nicergoline
    27848-84-6
  • US $30.00-62.00 / mg
  • 99.53%
  • TargetMol Chemicals Inc.

Nicergoline Spectrum

10-methoxy-1,6-dimethyl-ergoline-8-beta-methano5-bromo-3-pyridinecarboxy 10-methoxy-1,6-dimethyl-ergoline-8-beta-methano5-bromonicotinate(ester) 10-methoxy-1,6-dimethylergoline-8-methanol5-bromo-3-pyrindinecarboxylate(es 1-methyl-lumilysergol8-(5-bromonicotinate)10-methylether 8-beta-((5-bromonicotinoyloxy)methyl)-1,6-dimethyl-10-alpha-methoxyergoline fi6714 late(ester) mne nargoline nicergolin nicotergoline nimergoline NICERGOLINE Ergotop Indolo[4,3-fg]quinoline, ergoline-8-methanol deriv. Memoq Nicotinic acid, 5-bromo-, (10-methoxy-1,6-dimethylergolin-8b-yl)methyl ester (8CI) NSC 150531 Sermion TA 079 (8β)-10-methoxy-1,6-dimethylergoline-8-methanol5-bromo-3-pyridinecarboxylateester 10a-Methoxy-9,10-dihydrolyzergol (MDL) 1-Methyl-10a-Methoxy-9,10-dihydrolyzergol (1-MMDL) [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-Bromopyridine-3-carboxylate 5-Bromopyridine-3-carboxylic Acid [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl Ester ((6aR,9R,10aS)-10a-Methoxy-4,7-diMethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)Methyl 5-broMonicotinate Ergoline-8-Methanol,10-Methoxy-1,6-diMethyl-, 8-(5-broMo-3-pyridinecarboxylate), (8b)- Nicergoline for system suitability Nicergoline for peak identification nicergoline Fr.P 10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8.beta.)- 1,6-Dimethyl-8b-(5-bromonicotinoyloxymethyl)-10a-methoxyergoline Cergodum Circo-Maren Dilasenil Duracebrol Ergobel Ergoline-8b-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester) (8CI) Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8b)- (9CI) 5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHANOL ESTER 5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHYL ESTER (8BETA)-10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHANOL 5-BROMO-3-PYRIDINE CARBOXYLATE ESTER (+)-10-methoxy-1,6-dimethylergoline-8-beta-methanol5-bromonicotinate 10-methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat) Nicergoline powder CS-1354 Nicergoline, Sermion API-Nicergoline Nicergoline CRS Nicergoline for peak identification CRS Nicergoline> Nicergoline for system suitability CRS Nicergolinum Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 8-(5-bromo-3-pyridinecarboxylate), (8β)- Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-,5-bromo-3-pyridinecarboxylate (ester), (8b)- ((6aR,9R,10aS)-10a-methoxy-4,7-dimethyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl)methyl 5-chloronicotinate (2S,4R,7R)-2-methoxy-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraen-4-yl]methyl 5-bromopyridine-3-carboxylate Nicergoline impurity