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Substance Name: Metergoline [INN:BAN]
RN: 17692-51-2
UNII: 1501393LY5
InChIKey: WZHJKEUHNJHDLS-QTGUNEKASA-N

Note

  • A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.

Molecular Formula

  • C25-H29-N3-O2

Molecular Weight

  • 403.523
 

Classification Codes

  • Dopamine Agents
  • Dopamine Agonists
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Serotonin Agents
  • Serotonin Antagonists
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Names and Synonyms

Name of Substance

  • Metergoline [INN:BAN]
  • Methergoline

MeSH Heading

  • Metergoline

Synonyms

  • (((8-beta)-1,6-Dimethylergolin-8-yl)methyl)carbamic acid phenylmethyl ester
  • 1,6-Dimethyl-8-beta-carbobenzyloxaminomethyl-10-alpha-ergoline
  • 1-Methyl-8-beta-carbobenzyloxyaminomethyl-10-alpha-ergoline
  • 1-Methyl-N-carbobenzyloxydihydro-D-lysergamin
  • AHR 3009
  • Benzyl 1,6-dimethylergolin-8beta-ylmethylcarbamat
  • Carbamic acid, ((1,6-dimethylergolin-8-beta-yl)methyl)-, benzyl ester
  • D-8-beta-((Carbobenzoxyamino)methyl)-1,6-dimethyl-10-alpha-ergoline
  • D-8-beta-((Carboxyamino)methyl)-1,6-dimethylergoline I benzyl ester
  • D-N-Carbobenzoxydihydro-1-methyllysergamine I
  • D-N-Carboxydihydro-1-methyllysergamine I benzyl ester
  • EINECS 241-686-3
  • FI 6337
  • Liserdol
  • MCE
  • Metergolin
  • Metergolina
  • Metergolina [DCIT]
  • Metergolina [Spanish]
  • Metergoline
  • Metergolinum
  • Metergolinum [INN-Latin]
  • Metergolinum [Latin]
  • Methergoline
  • Substance 355/255
  • UNII-1501393LY5

Systematic Names

  • (+)-N-(Carboxy)-1-methyl-9,10-dihydrolysergamine benzyl ester
  • Carbamic acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, benzyl ester
  • Carbamic acid, (((8-beta)-1,6-dimethylergolin-8-yl)methyl)-, phenylmethyl ester (9CI)
  • Carbamic acid, (((8beta)-1,6-dimethylergolin-8-yl)methyl)-, phenylmethyl ester
  • Lysergamine, N-carboxy-9,10-dihydro-1-methyl-, benzyl ester (7CI)
  • Metergoline

Registry Numbers

CAS Registry Number

  • 17692-51-2

FDA UNII

  • 1501393LY5

System Generated Number

  • 0017692512

Structure Descriptors

InChI

1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1

InChIKey

WZHJKEUHNJHDLS-QTGUNEKASA-N

Smiles

c12c3[C@@H]4[C@H]([N@@](C[C@@H](C4)CNC(OCc4ccccc4)=O)C)Cc1cn(c2ccc3)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 85mg/kg (85mg/kg)   Nature. Vol. 207, Pg. 421, 1965.
mouse LD50 intravenous 21200ug/kg (21.2mg/kg)   United States Patent Document. Vol. #4176182,
mouse LD50 oral 430mg/kg (430mg/kg)   Nature. Vol. 207, Pg. 421, 1965.
rabbit LD50 intravenous 20mg/kg (20mg/kg)   Nature. Vol. 207, Pg. 421, 1965.