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Nicergoline

Nicergoline structure

CAS No:
27848-84-6
Formula:
C24H26BrN3O3
Chemical Name:
Nicergoline
Synonyms:
Ergoline-8-methanol,10-methoxy-1,6-dimethyl-,8-(5-bromo-3-pyridinecarboxylate),(8β)-;Ergoline-8β-methanol,10-methoxy-1,6-dimethyl-,5-bromonicotinate (ester);Ergoline-8-methanol,10-methoxy-1,6-dimethyl-,5-bromo-3-pyridinecarboxylate (ester),(8β)-;Nicotinic acid,5-bromo-,(10-methoxy-1,6-dimethylergolin-8β-yl)methyl ester;Indolo[4,3-fg]quinoline,ergoline-8-methanol deriv.;MNE;Nicotergoline;1,6-Dimethyl-8β-(5-bromonicotinoyloxymethyl)-10α-methoxyergoline;Nicergoline;Sermion;TA 079;Ergotop;Ergobel;Cergodum;Circo-Maren;Duracebrol;Vasospan;Memoq;Nicergolent;FI 6714;Dilasenil;NSC 150531;24705-56-4;37415-54-6;47673-09-6
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

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 ch

Solid

Nicergoline is an organonitrogen heterocyclic compound and an organic heterotetracyclic compound.|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.|An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It may ameliorate cognitive deficits in CEREBROVASCULAR DISORDERS.

Nicergoline Basic Attributes

Molecular Weight：

484.39

Exact Mass：

484.39

EC Number：

248-694-6

UNII：

JCV8365FWN

NSC Number：

757853

DSSTox ID：

DTXSID7045607

ATC Code：

C - Cardiovascular system

HScode：

29396100

Characteristics

PSA：

56.6

XLogP3：

3.2

Appearance：

Solid

Density：

1.5±0.1 g/cm3

Melting Point：

136-138 °C

Boiling Point：

594.351°C at 760 mmHg

Flash Point：

313.3±30.1 °C

Refractive Index：

1.670

Water Solubility：

soluble in alcohol, chloroform, and acetone. Insoluble in water.

Storage Conditions：

2-8°C

Vapor Pressure：

0mmHg at 25°C

Toxicity：

LD50 in male mice, rats (mg/kg): 860, 2800 orally; 46, 43 i.v. (Neumann, Lauschner)

Collision Cross Section：

213.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

1544

wgk germany：

hazard class code：

safety instructions：

RTECS Number：

KE6341000

Marks：

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P301 + P312 + P330

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 233 companies from 6 notifications to the ECHA C&L Inventory.

Drug Information

Drug Indication：

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

Pharmacology：

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.

MeSH：

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)|Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

Mechanism of Action：

Nicergoline 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. Therefore the mechanism of Nicergoline is to increase vascular circulation in the brain, thereby enhancing the transmission of nerve signals across the nerve fibres, which secrete acetylcholine as a neural transmitter.

MeSH Entry Terms：

Circo Maren

Nicergoline Use and Manufacturing

Methods of Manufacturing

1-methyl-10α-methoxy-dihydroergoline (middle product 2)Add to 20g triethylamine andIn a mixture of 300 g of chloroform, 5-bromonicotinoyl chloride 75 g was added with stirring.Control the temperature at 20-30 °C, The reaction was carried out for 2 hours (in terms of volume ratio, ethyl acetate:heptane=1:1 detection reaction end point), 500 ml of purified water was added, organic layer was separated, and water was added.The layers were extracted twice with chloroform (300 ml*2), and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure to obtain Nigeran.54.1g crude forest products, 200ml of ergoline crude product, acetone, and 1g of activated carbon, stirred and dissolved at 30-60°C, filtered while still hot and filtered.The solution was frozen and crystallized at -5OC for 6 hours, filtered, and dried under reduced pressure to give 53.6 g of Nemetralin with a yield of 91.2percent.

Uses

antipsychotic

Computed Properties

Molecular Weight:484.4
XLogP3:3.2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:483.11575
Monoisotopic Mass:483.11575
Topological Polar Surface Area:56.6
Heavy Atom Count:31
Complexity:681
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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