Nicergoline

Modify Date: 2024-01-01 19:46:10

Nicergoline Structure
Nicergoline structure
 Common Name Nicergoline
CAS Number 27848-84-6 Molecular Weight 484.385
Density 1.5±0.1 g/cm3 Boiling Point 594.4±50.0 °C at 760 mmHg
Molecular Formula C24H26BrN3O3 Melting Point 136-138°
MSDS Chinese USA Flash Point 313.3±30.1 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Nicergoline


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].

 Names

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
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
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.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
KE6341000
CHEMICAL NAME :
Ergoline-8-beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester)
CAS REGISTRY NUMBER :
27848-84-6
LAST UPDATED :
199612
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C24-H26-Br-N3-O3
MOLECULAR WEIGHT :
484.44
WISWESSER LINE NOTATION :
T C6656 1A P GN LNTT&&J CO1 G1 L1 E1OV- CT6NJ EE

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1193 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,735,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1571 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,735,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
776 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1223,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
633 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1223,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
198 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - body temperature decrease
REFERENCE :
JOPHDQ Journal of Pharmacobio-Dynamics. (Japan Pub. Trading Co. (USA), 1255 Howard St., San Francisco, CA 94103) V.1- 1978- Volume(issue)/page/year: 10,35,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1025 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 19,735,1988
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
46 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
790 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,5907,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4200 mg/kg/5W-C
TOXIC EFFECTS :
Behavioral - fluid intake Kidney, Ureter, Bladder - urine volume increased Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,5897,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14600 mg/kg/52W-C
TOXIC EFFECTS :
Behavioral - fluid intake Gastrointestinal - changes in structure or function of salivary glands Kidney, Ureter, Bladder - urine volume increased
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,5897,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
81900 mg/kg/26W-I
TOXIC EFFECTS :
Endocrine - changes in spleen weight Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1344 mg/kg/6W-I
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - acute pulmonary edema Related to Chronic Data - death
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
12 gm/kg/30D-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,5907,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
24570 mg/kg/26W-I
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1206,1979 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2475 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6375,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
2600 mg/kg
SEX/DURATION :
female 17-22 day(s) after conception lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6375,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
5175 mg/kg
SEX/DURATION :
female 14 day(s) pre-mating female 1-7 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6375,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20475 mg/kg
SEX/DURATION :
male 91 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
REFERENCE :
KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6375,1986

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S36
RIDADR UN 1544
WGK Germany 3
RTECS KE6341000
Packaging Group III
Hazard Class 6.1(b)

 Precursor & DownStream

Precursor  0

DownStream  2

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 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)
4,6,6a,7,8,9,10,10a-Octahydro-10aa-methoxy-4,7-dimethylindolo[4,3-fg]quinoline-9-methanol 5-Bromonicotinate
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-3-carboxylate
Nicergoline [USAN:BAN:INN:JAN]
Ergotop
[(8β)-10-methoxy-1,6-dimethylergolin-8-yl]methyl 5-bromopyridine-3-carboxylate
Memoq
8b-[(5-Bromonicotinoyloxy)methyl]-1,6-dimethyl-10a-methoxyergoline
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