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Substance Name: Ergometrine [INN:BAN]
RN: 60-79-7
UNII: WH41D8433D
InChIKey: WVVSZNPYNCNODU-XTQGRXLLSA-N

Note

  • An ergot alkaloid (ERGOT ALKALOIDS) with uterine and vascular smooth muscle contractile properties.

Molecular Formula

  • C19-H23-N3-O2

Molecular Weight

  • 325.4097
 

Classification Codes

  • Human Data
  • Natural Product
  • Oxytocics
  • Reproductive Control Agents

Names and Synonyms

Name of Substance

  • Ergometrine [INN:BAN]
  • Ergonovine

MeSH Heading

  • Ergonovine

Synonyms

  • 9,10-Didehydro-N-(2-hydroxy-1-methylethyl)-6-methylergoline-8beta(S)-carboxamide
  • 9,10-Didehydro-N-(alpha-(hydroxymethyl)ethyl)-6-methylergoline-8-beta-carboxamide
  • Basergin
  • D-Lysergic acid 1-hydroxymethylethylamide
  • D-Lysergic acid-L-propanolamide
  • EINECS 200-485-0
  • Ergobasine
  • Ergoklinine
  • Ergometrin
  • Ergometrina
  • Ergometrina [INN-Spanish]
  • Ergometrine
  • Ergometrinum
  • Ergometrinum [INN-Latin]
  • Ergonovine
  • Ergostetrine
  • Ergotocine
  • HSDB 4075
  • L-Lysergic-L(beta-hydroxyisopropylamide)
  • Lysergamide, N-((S)-2-hydroxy-1-methylethyl)-
  • Lysergic acid propanolamide
  • Margonovine
  • N-(1-(Hydroxymethyl)ethyl)-D-lysergamide
  • N-(2-Hydroxy-1-methylethyl)-D(+)-lysergamide
  • N-(alpha-(Hydroxymethyl)ethyl)-D-lysergamide
  • Neofemergen
  • Secacornin
  • Secometrin
  • UNII-WH41D8433D

Systematic Names

  • Ergoline-8-beta-carboxamide, 9,10-didehydro-N-((S)-2-hydroxy-1-methylethyl)-6-methyl-
  • Ergoline-8-carboxamide, 9,10-didehydro-N-(2-hydroxy-1-methylethyl)-6-methyl-, (8beta(S))-
  • Ergometrine

Registry Numbers

CAS Registry Number

  • 60-79-7

FDA UNII

  • WH41D8433D

Other Registry Numbers

  • 11002-48-5
  • 78207-83-7

System Generated Number

  • 0000060797

Structure Descriptors

InChI

InChI=1S/C19H23N3O2/c1-11(10-23)21-19(24)13-6-15-14-4-3-5-16-18(14)12(8-20-16)7-17(15)22(2)9-13/h3-6,8,11,13,17,20,23H,7,9-10H2,1-2H3,(H,21,24)/t11-,13+,17+/m0/s1

InChIKey

WVVSZNPYNCNODU-XTQGRXLLSA-N

Smiles

C[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD intramuscular > 10gm/kg (10000mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 119, Pg. 1302, 1935.
guinea pig LDLo intravenous 80mg/kg (80mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 107, 1973.
infant TDLo intramuscular 93mg/kg (93mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 South African Medical Journal. Vol. 46, Pg. 2052, 1972.
infant TDLo intramuscular 138mg/kg (138mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Archives of Disease in Childhood. Vol. 55, Pg. 68, 1980.
infant TDLo unreported 176ug/kg (0.176mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Journal of Obstetrics and Gynaecology of the British Commonwealth. Vol. 79, Pg. 764, 1972.
mouse LD50 intravenous 144mg/kg (144mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT		 Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 130, 1952.
mouse LD50 unreported 144mg/kg (144mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 98, Pg. 335, 1954.
rabbit LDLo intravenous 6mg/kg (6mg/kg)   Handbuch der Experimentellen Pharmakologie. Vol. 6, Pg. 180, 1938.
rat LDLo subcutaneous 500mg/kg (500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 119, Pg. 1302, 1935.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 162 deg C   EXP
pKa Dissociation Constant 6.8 (none)   EXP
log P (octanol-water) 0.520 (none)   EST
Atmospheric OH Rate Constant 4.13E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.