CAS 27848-84-6|Nicergoline

Introduction：Basic information about CAS 27848-84-6|Nicergoline, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Nicergoline BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles30
7. Synonyms

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	ChineseUSA	Flash Point	313.3±30.1 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	Nicergoline
Synonym	More Synonyms

Nicergoline BiologicalActivity

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 ReceptorResearch Areas >>Neurological DiseaseNatural 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.

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
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)

Articles30

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Heparan sulfate (HS) is a randomly sulfated polysaccharide that is present on the cell surface and in the extracellular matrix. The sulfated structures of HS were synthesized by multiple HS sulfotrans...

[Nicergoline, ibudilast, ifenprodil tartrate].

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Protective effects of nicergoline against neuronal cell death induced by activated microglia and astrocytes.

Brain Res. 1066(1-2) , 78-85, (2005)

We examined the neuroprotective role of nicergoline in neuron-microglia or neuron-astrocytes co-cultures. Nicergoline, an ergoline derivative, significantly suppressed the neuronal cell death induced ...

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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