ChemicalBook > CAS DataBase List > Nicergoline

Nicergoline

Product Name
Nicergoline
CAS No.
27848-84-6
Chemical Name
Nicergoline
Synonyms
mne;Memoq;fi6714;TA 079;Ergobel;CS-1354;Ergotop;Sermion;Cergodum;Dilasenil
CBNumber
CB9728301
Molecular Formula
C24H26BrN3O3
Formula Weight
484.39
MOL File
27848-84-6.mol
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Nicergoline Property

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).
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
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001352
Product name
Nicergoline for system suitability
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0001352
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
N7889
Product name
Nicergoline
Purity
analytical standard, for drug analysis
Packaging
100mg
Price
$44.1
Updated
2024/03/01
TCI Chemical
Product number
N0904
Product name
Nicergoline
Purity
>98.0%(HPLC)(T)
Packaging
100mg
Price
$37
Updated
2024/03/01
TCI Chemical
Product number
N0904
Product name
Nicergoline
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$221
Updated
2024/03/01
Alfa Aesar
Product number
J63295
Product name
Nicergoline
Packaging
100mg
Price
$80.65
Updated
2024/03/01
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Nicergoline Chemical Properties,Usage,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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View Lastest Price from Nicergoline manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Nicergoline 27848-84-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%min
Supply Ability
10kg
Release date
2021-11-02
Hebei Weibang Biotechnology Co., Ltd
Product
Nicergoline 27848-84-6
Price
US $10.00/KG
Min. Order
100KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-21
Hebei Yanxi Chemical Co., Ltd.
Product
Nicergoline 27848-84-6
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100tons
Release date
2023-08-15

27848-84-6, NicergolineRelated Search:

Methoxyacetic acid Methanol 2-Methoxyethanol Acetonitrile (Trifluoromethoxy)benzene Anisole Methoxydiethylborane POLY(ETHYLENE GLYCOL) METHYL ETHER ACRYLATE p-Anisidine Basic Violet 1 m-Anisyl alcohol Methyl acrylate p-Anisaldehyde Kresoxim-methyl Methylparaben Methyl (+)-N-METHYLEPHEDRINE Hexyl nicotinate

  • 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)
  • 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
  • Nicergoline powder
  • CS-1354
  • Nicergoline, Sermion
  • API-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 CRS
  • Nicergoline for peak identification CRS
  • Nicergoline&gt
  • 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)-
  • Nicergoline impurity
  • ((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