3738
T3D3685
Ergonovine
Ergonovine is only found in individuals that have used or taken this drug. It is an ergot alkaloid with uterine and vascular smooth muscle contractile properties. [PubChem] Ergonovine directly stimulates the uterine muscle to increase force and frequency of contractions. With usual doses, these contractions precede periods of relaxation; with larger doses, basal uterine tone is elevated and these relaxation periods will be decreased. Contraction of the uterine wall around bleeding vessels at the placental site produces hemostasis. Ergonovine also induces cervical contractions. The sensitivity of the uterus to the oxytocic effect is much greater toward the end of pregnancy. The oxytocic actions of ergonovine are greater than its vascular effects. Ergonovine, like other ergot alkaloids, produces arterial vasoconstriction by stimulation of alpha-adrenergic and serotonin receptors and inhibition of endothelial-derived relaxation factor release. It is a less potent vasoconstrictor than ergotamine. As a diagnostic aid (coronary vasospasm), ergonovine causes vasoconstriction of coronary arteries.
60-79-7
443884
C19H23N3O2
White powder.
162°C
2.68 mg/mL at 25°C
Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) Absorption is rapid and complete after oral or intramuscular administration.
Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Ergometrine is also known to have a non-receptor specific oxytocic activity. (A2914, A2915, A2916)
Hepatic.
Route of Elimination: Thought to be eliminated by non-renal mechanisms (i.e. hepatic metabolism, excretion in feces)
Half Life: t<sub>1/2 α</sub>=10 minutes; t<sub>1/2 β</sub>=2 hours
No indication of carcinogenicity to humans (not listed by IARC).
Ergoline alkaloids occur in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. Ergometrine can also be synthesized from (+)-lysergic acid and L-(+)-2-aminopropanol. It has medical use in obstetrics to facilitate delivery of the placenta and to prevent bleeding after childbirth by causing smooth muscle tissue in the blood vessel walls to narrow, thereby reducing blood flow. For this is usually combined with oxytocin (Syntocinon) as syntometrine. (L1918, L1922)
Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (A2913)
Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (L1920)
Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (L1921)
2010-04-21T17:59:34Z
2014-12-24T20:26:22Z
Ergonovine
C07543
4822
DB01253
true
[H][C@](C)(CO)N=C(O)[C@@]1([H])CN(C)[C@]2([H])CC3=CNC4=CC=CC(=C34)C2=C1
C19H23N3O2
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
325.4048
325.179026995
Exogenous
Solid
0.9
HMDB15383
CHEMBL119443
391970