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Substance Name: Nicergoline [USAN:INN:BAN:JAN]
RN: 27848-84-6
UNII: JCV8365FWN
InChIKey: YSEXMKHXIOCEJA-FVFQAYNVSA-N

Note

  • An ergot derivative that has been used as a cerebral vasodilator and in peripheral vascular disease. It may ameliorate cognitive deficits in CEREBROVASCULAR DISORDERS.

Molecular Formula

  • C24-H26-Br-N3-O3

Molecular Weight

  • 484.3914
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Cardiovascular Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Neurotransmitter Agents
  • Nootropic Agents
  • Reproductive Effect
  • Vasodilator
  • Vasodilator Agents
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Names and Synonyms

Name of Substance

  • Nicergoline
  • Nicergoline [USAN:INN:BAN:JAN]

MeSH Heading

  • Nicergoline

Synonyms

  • (+)-10-Methoxy-1,6-dimethylergoline-8-beta-methanol 5-bromonicotinate
  • 1-Methyl-lumilysergol 8-(5-bromonicotinate) 10-methyl ether
  • 10-Methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat)
  • 10-Methoxy-1,6-dimethyl-ergolin-8-beta-methanol-(5-bromnicotinat) [German]
  • 10-Methoxy-1,6-dimethylergoline-8-methanol 5-bromo-3-pyrindinecarboxylate (ester)
  • 10-Methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate
  • 10-Methoxy-1,6-dimethylergoline-8beta-methanol 5-bromonicotinate (ester)
  • 8-beta-((5-Bromonicotinoyloxy)methyl)-1,6-dimethyl-10-alpha-methoxyergoline
  • BRN 4828393
  • EINECS 248-694-6
  • Ergoline-8-beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester)
  • FI 6714
  • Nicergolin
  • Nicergolin [German]
  • Nicergolina
  • Nicergolina [DCIT]
  • Nicergoline
  • Nicergolinum
  • Nicergolinum [INN-Latin]
  • Nicotergoline
  • Nimergoline
  • Nimergoline base
  • NSC 150531
  • RP 19651
  • Sermion
  • UNII-JCV8365FWN

Systematic Names

  • Ergoline-8-beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester)
  • Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, (8beta)-, 5-bromo-3-pyridinecarboxylate (ester)
  • Ergoline-8-methanol, 10-methoxy-1,6-dimethyl-, 5-bromo-3-pyridinecarboxylate (ester), (8beta)-
  • Ergoline-8beta-methanol, 10-methoxy-1,6-dimethyl-, 5-bromonicotinate (ester)
  • Nicergoline

Registry Numbers

CAS Registry Number

  • 27848-84-6

FDA UNII

  • JCV8365FWN

System Generated Number

  • 0027848846

Structure Descriptors

InChI

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

InChIKey

YSEXMKHXIOCEJA-FVFQAYNVSA-N

Smiles

CO[C@]12C[C@@H](COC(=O)c3cncc(Br)c3)CN(C)[C@@H]1Cc4cn(C)c5cccc2c45

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 20mg/kg (20mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 1206, 1979.
dog LD50 oral 790mg/kg (790mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 20, Pg. 5907, 1986.
mouse LD50 intraperitoneal 198mg/kg (198mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Journal of Pharmacobio-Dynamics. Vol. 10, Pg. 35, 1987.
mouse LD50 intravenous 46mg/kg (46mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 1206, 1979.
mouse LD50 oral 633mg/kg (633mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 1223, 1979.
mouse LD50 subcutaneous 1025mg/kg (1025mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.
rat LD50 intraperitoneal 1571mg/kg (1571mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.
rat LD50 intravenous 42mg/kg (42mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 1206, 1979.
rat LD50 oral 1193mg/kg (1193mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 735, 1988.
rat LD50 subcutaneous 776mg/kg (776mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 29, Pg. 1223, 1979.