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ergometrine
Lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced. The maleate salt has also been used in the diagnosis of oesophageal spasm, and in a provocation test for the diagnosis of Prinzmetal's angina.


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05. Industrial Uses: pharmaceutical [CHEBI:52217] > drug [CHEBI:23888] > oxytocic [CHEBI:36063]
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05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 oxytocic [CHEBI:36063] (8) 
 ergometrine [CHEBI:4822] (1)
 diagnostic agent [CHEBI:33295] (53) 
 ergometrine [CHEBI:4822] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 terpenoid indole alkaloid [CHEBI:65321] (57) 
 hemiterpenoid indole alkaloid [CHEBI:65322] (28) 
 ergot alkaloid [CHEBI:23943] (28) 
 ergometrine [CHEBI:4822] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organonitrogen compound [CHEBI:35352] (6705) 
 alkaloid [CHEBI:22315] (473) 
 indole alkaloid [CHEBI:38958] (144) 
 terpenoid indole alkaloid [CHEBI:65321] (57) 
 hemiterpenoid indole alkaloid [CHEBI:65322] (28) 
 ergot alkaloid [CHEBI:23943] (28) 
 ergometrine [CHEBI:4822] (1)
ChEBI Compound Accession Identifier  [CHEBI:4822]
ChEBI Compound Description  Lysergamide in which one of the hydrogens attached to the amide nitrogen is substituted by a 1-hydroxypropan-2-yl group (S-configuration). An ergot alkaloid that has a particularly powerful action on the uterus, its maleate (and formerly tartrate) salt is used in the active management of the third stage of labour, and to prevent or treat postpartum of postabortal haemorrhage caused by uterine atony: by maintaining uterine contraction and tone, blood vessels in the uterine wall are compressed and blood flow reduced. The maleate salt has also been used in the diagnosis of oesophageal spasm, and in a provocation test for the diagnosis of Prinzmetal's angina.
ChEBI Compound Identification Number  4822
ChEBI InChI Value  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
ChEBI InChIKey Value  WVVSZNPYNCNODU-XTQGRXLLSA-N
ChEBI Compound Name  ergometrine
ChEBI SMILES Value  [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@H](CN2C)C(=O)N[C@@H](C)CO)c34
ChEBI Substance ID  99313644
ChEBI URL  ChEBI:4822
ChemSpider ID  391970
Ontomatica Chemical Accession Key (OnChAKey)  WVVSZNPYNCNODU_XTQGRXLLSA_N_000_000000
PubChem Compound ID  443884