| Identification | Back Directory | [Name]
Nicergoline | [CAS]
27848-84-6 | [Synonyms]
mne
Memoq
TA 079
fi6714
CS-1354
Ergotop
Ergobel
Sermion
Cergodum
Dilasenil
nargoline
nicergolin
Duracebrol
NSC 150531
Circo-Maren
late(ester)
nimergoline
NICERGOLINE
Nicergolinum
nicotergoline
Nicergoline>
Nicergoline CRS
API-Nicergoline
nicergoline Fr.P
Nicergoline powder
Nicergoline, Sermion
Nicergoline impurity
Nicergoline USP/EP/BP
Nicergoline for system suitability
Nicergoline for peak identification
Nicergoline for system suitability CRS
10a-Methoxy-9,10-dihydrolyzergol (MDL)
Nicergoline for peak identification CRS
1-Methyl-10a-Methoxy-9,10-dihydrolyzergol (1-MMDL)
Indolo[4,3-fg]quinoline, ergoline-8-methanol deriv.
1-methyl-lumilysergol8-(5-bromonicotinate)10-methylether
10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate
1,6-Dimethyl-8b-(5-bromonicotinoyloxymethyl)-10a-methoxyergoline
10-methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat)
5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHYL ESTER
(+)-10-methoxy-1,6-dimethylergoline-8-beta-methanol5-bromonicotinate
5-BROMONICOTINIC ACID 10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHANOL ESTER
10-methoxy-1,6-dimethyl-ergoline-8-beta-methano5-bromonicotinate(ester)
10-methoxy-1,6-dimethyl-ergoline-8-beta-methano5-bromo-3-pyridinecarboxy
10-methoxy-1,6-dimethylergoline-8-methanol5-bromo-3-pyrindinecarboxylate(es
8-beta-((5-bromonicotinoyloxy)methyl)-1,6-dimethyl-10-alpha-methoxyergoline
Ergoline-8b-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester) (8CI)
(8β)-10-methoxy-1,6-dimethylergoline-8-methanol5-bromo-3-pyridinecarboxylateester
Nicotinic acid, 5-bromo-, (10-methoxy-1,6-dimethylergolin-8b-yl)methyl ester (8CI)
[(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-Bromopyridine-3-carboxylate
Ergoline-8-Methanol,10-Methoxy-1,6-diMethyl-, 8-(5-broMo-3-pyridinecarboxylate), (8b)-
Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 8-(5-bromo-3-pyridinecarboxylate), (8β)-
(8BETA)-10-METHOXY-1,6-DIMETHYLERGOLINE-8-METHANOL 5-BROMO-3-PYRIDINE CARBOXYLATE ESTER
Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-,5-bromo-3-pyridinecarboxylate (ester), (8b)-
5-Bromopyridine-3-carboxylic Acid [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl Ester
Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8.beta.)-
Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8b)- (9CI)
((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
((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
[(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 | [EINECS(EC#)]
248-694-6 | [Molecular Formula]
C24H26BrN3O3 | [MDL Number]
MFCD00869626 | [MOL File]
27848-84-6.mol | [Molecular Weight]
484.39 |
| Chemical Properties | Back Directory | [Appearance]
Fine to granular, white or yellowish powder. | [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) | [color ]
White to Off-White | [Water Solubility ]
Soluble in alcohol, chloroform, and acetone. Insoluble in water. | [Merck ]
14,9496 |
| Hazard Information | Back Directory | [Chemical Properties]
Fine to granular, white or yellowish powder. | [Uses]
antipsychotic | [Brand name]
Sermion (Farmitalia, Societa Farmaceutici
Italia, Italy). | [Biological Activity]
α -adrenergic, vasodilator. Cognitive enhancer. | [Originator]
Sermion,Farmitalia,Italy,1974 | [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. | [Therapeutic Function]
Vasodilator | [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 Data | Back Directory | [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 | [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. | [Toxicity]
LD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner) |
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