CAS Number27848-84-6
SynonymsErgobel; Nicergoline; Sermion; MNE; Cergodum; fi6714; nigergoline; 3-Pyridinecarboxylic acid, 5-bromo-, [(8β)-10-methoxy-1,6-dimethylergolin-8-yl]methyl ester; Dilasenil; Cholergol; [(8β)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromonicotinate; Nargoline; 5-Bromopyridine-3-carboxylic Acid [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl Ester; 10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate ester; TA 079; (8b)-10-Methoxy-1,6-dimethylergoline-8-methanol 5-Bromo-3-pyridinecarboxylate (Ester); 5-bromo-nicotinic acid 10-methoxy-1,6-dimethyl-ergolin-8-ylmethyl ester; 1-Methyllumilysergol 8-(5-Bromonicotinate) 10-Methyl Ether; ergoline-8-methanol 10-methoxy-1,6-dimethyl-,8-(5-bromo-3-pyridinecarboxylate); [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-Bromopyridine
Molecular FormulaC24H26BrN3O3
Molecular Weight484.39
Purity≥97 (TLC)%
Density1.5±0.1 g/cm3
Boiling Point594.4±50.0 °C at 760 mmHg
Melting Point136-138°
AppearanceSolid;White to Light yellow powder to crystal
EINECS248-694-6
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 27848-84-6 |
| Catalog No. | 2A-9011632 |
| Chinese Name | 尼麦角林 |
| Synonyms | Ergobel; Nicergoline; Sermion; MNE; Cergodum; fi6714; nigergoline; 3-Pyridinecarboxylic acid, 5-bromo-, [(8β)-10-methoxy-1,6-dimethylergolin-8-yl]methyl ester; Dilasenil; Cholergol; [(8β)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromonicotinate; Nargoline; 5-Bromopyridine-3-carboxylic Acid [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl Ester; 10-Methoxy-1,6-dimethylergoline-8β-methanol 5-bromonicotinate ester; TA 079; (8b)-10-Methoxy-1,6-dimethylergoline-8-methanol 5-Bromo-3-pyridinecarboxylate (Ester); 5-bromo-nicotinic acid 10-methoxy-1,6-dimethyl-ergolin-8-ylmethyl ester; 1-Methyllumilysergol 8-(5-Bromonicotinate) 10-Methyl Ether; ergoline-8-methanol 10-methoxy-1,6-dimethyl-,8-(5-bromo-3-pyridinecarboxylate); [(8R,10S)-10-Methoxy-1,6-dimethylergolin-8-yl]methyl 5-Bromopyridine |
| Molecular Formula | C24H26BrN3O3 |
| Molecular Weight | 484.39 |
| Purity | ≥97 (TLC) |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 594.4±50.0 °C at 760 mmHg |
| Melting Point | 136-138° |
| Appearance | Solid;White to Light yellow powder to crystal |
| Water Solubility | Practically insoluble in water, freely soluble in |
| Storage Condition | 2-8℃ |
| Packaging | III |
| Application | Nicergoline inhibits Alpha-1A adrenergic receptors. |
| EINECS | 248-694-6 |
| PubChem ID | 329818675 |
| MDL Number | MFCD00869626 |
| SMILES | [H][C@@]12Cc3cn(C)c4cccc(c34)[C@]1(C[C@@H](COC(=O)c5cncc(Br)c5)CN2C)OC |
| InChI | 1S/C24H26BrN3O3/c1-27-13-17-8-21-24(30-3,19-5-4-6-20(27)22(17)19)9-15(12-28(21)2)14-31-23(29)16-7-18(25)11-26-10-16/h4-7,10-11,13,15,21H,8-9,12,14H2,1-3H3/t15-,21-,24+/m1/s1 |
| InChI Key | YSEXMKHXIOCEJA-FVFQAYNVSA-N |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/11632_1_27848_84_6.pdf |
| Bioactivity | Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins.Target: Alpha-1A adrenergic receptorNicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Nicergoline displaced [3H]-prazosin bound to rat forebrain membranes pretreated with chloroethylclonidine (pKi = 9.9 ± 0.2) at concentrations 60-fold lower than in rat liver membranes (pKi = 8.1 ± 0.2). Finally, of the nicergoline metabolites studied, lumilysergol acted as a modest alpha 1 antagonist (bromonicotinic acid was devoid of alpha 1 antagonist activity). In conclusion, nicergoline is a potent and selective alpha 1A-adrenoceptor subtype antagonist, an alpha 1-adrenoceptor subtype which is mainly represented in resistance arteries [1]. Related Catalog Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Neurological Disease Natural Products >> Alkaloid References [1]. Alvarez-Guerra, M., N. Bertholom, and R.P. Garay, Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol, 1999. 13(1): p. 50-8. Chemical & Physical Properties Density 1.5±0.1 g/cm3 Boiling Point 594.4±50.0 °C at 760 mmHg Melting Point 136-138° Molecular Formula C24H26BrN3O3 Molecular Weight 484.385 Flash Point 313.3±30.1 °C Exact Mass 483.115753 PSA 56.59000 LogP 4.34 Vapour Pressure 0.0±1.7 mmHg at 25°C Index of Refraction 1.670 InChIKey YSEXMKHXIOCEJA-FVFQAYNVSA-N SMILES COC12CC(COC(=O)c3cncc(Br)c3)CN(C)C1Cc1cn(C)c3cccc2c13 Storage condition 2-8°C Water Solubility Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent). | Soluble in alcohol, chloroform, and acetone. Insoluble in water. |
| Use of | Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins.Target: Alpha-1A adrenergic receptorNicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Nicergoline displaced [3H]-prazosin bound to rat forebrain membranes pretreated with chloroethylclonidine (pKi = 9.9 ± 0.2) at concentrations 60-fold lower than in rat liver membranes (pKi = 8.1 ± 0.2). Finally, of the nicergoline metabolites studied, lumilysergol acted as a modest alpha 1 antagonist (bromonicotinic acid was devoid of alpha 1 antagonist activity). In conclusion, nicergoline is a potent and selective alpha 1A-adrenoceptor subtype antagonist, an alpha 1-adrenoceptor subtype which is mainly represented in resistance arteries [1]. Properties Articles30 Name Nicergoline Synonym More Synonyms Nicergoline Biological Activity Description Nicergoline is an ergot derivative used to treat senile dementia and other disorders with vascular origins.Target: Alpha-1A adrenergic receptorNicergoline acts by inhibiting the postsynaptic alpha(1)-adrenoceptors on vascular smooth muscle. This inhibits the vasoconstrictor effect of circulating and locally released catecholamines (epinephrine and norepinephrine), resulting in peripheral vasodilation. Nicergoline displaced [3H]-prazosin bound to rat forebrain membranes pretreated with chloroethylclonidine (pKi = 9.9 ± 0.2) at concentrations 60-fold lower than in rat liver membranes (pKi = 8.1 ± 0.2). Finally, of the nicergoline metabolites studied, lumilysergol acted as a modest alpha 1 antagonist (bromonicotinic acid was devoid of alpha 1 antagonist activity). In conclusion, nicergoline is a potent and selective alpha 1A-adrenoceptor subtype antagonist, an alpha 1-adrenoceptor subtype which is mainly represented in resistance arteries [1]. Related Catalog Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Research Areas >> Neurological Disease Natural Products >> Alkaloid References [1]. Alvarez-Guerra, M., N. Bertholom, and R.P. Garay, Selective blockade by nicergoline of vascular responses elicited by stimulation of alpha 1A-adrenoceptor subtype in the rat. Fundam Clin Pharmacol, 1999. 13(1): p. 50-8. Chemical & Physical Properties Molecular Formula C24H26BrN3O3 Exact Mass 483.115753 PSA 56.59000 Index of Refraction 1.670 InChIKey YSEXMKHXIOCEJA-FVFQAYNVSA-N Water Solubility Practically insoluble in water, freely soluble in methylene chloride, soluble in ethanol (96 per cent). | Soluble in alcohol, chloroform, and acetone. Insoluble in water. |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified Nicergoline Modification Number: 4 |
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