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Ergovaline

HCID 104843
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Grundinformationen

CAS
2873-38-3
Standard-SMILES
CC(C)[C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C)(NC(=O)[C@@H]3C=C4c5cccc6[nH]cc(c56)C[C@H]4N(C)C3)C(=O)N12
InChIKey
BGHDUTQZGWOQIA-VQSKNWBGSA-N
Summenformel
C29H35N5O5
Durchschnittliche Molmasse
533,6 g/mol
Monoisotopische Masse
533,26381923

Überblick

Ergovaline is a peptide ergot alkaloid.

Namen und Bezeichner

Bevorzugter Name
Ergovaline
IUPAC
(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
Englischer Name
ergovaline
Summenformel
C29H35N5O5
Molmasse
533.62

Namen und Synonyme

Ergovaline2873-38-3059E2O9IV4DTXSID1089324312'-Hydroxy-2'-methyl-5'alpha-(1-methylethyl)-ergotaman-3',6',18-trione(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide12'-hydroxy-2'-methyl-5' alpha-(1-methylethyl)-ergotaman-3',6',18-trione(6aR,9R)-N-((1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo(4,3-fg)quinoline-9-carboxamideRefChem:137563DTXCID401323176ERGOTAMAN-3',6',18-TRIONE, 12'-HYDROXY-2'-METHYL-5'-(1-METHYLETHYL)-, (5'ALPHA)-RN-(2-hydroxy-4-methyl-5,8-dioxo-7-(propan-2-yl)-3-oxa-6,9-diazatricyclo(7.3.0.02,6)dodecan-4-yl)-6-methyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
Weitere Namen anzeigen
Brexpiprazole Impurity 96Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'α)-
UNII-059E2O9IV4SCHEMBL14887086CHEBI:184047FE31073Ergotaman-3',6',18-trione, 12'-hydroxy-2'-methyl-5'-(1-methylethyl)-, (5'alpha)-NS00094895Q538583412'-Hydroxy-2'-methyl-3',6',18-trioxo-5'alpha-(propan-2-yl)ergotaman

Datenbank-Bezeichner

CAS
2873-38-3
PubChem CID
104843
DTXSID
DTXSID10893243
ChEBI
CHEBI:184047
UNII
059E2O9IV4
Nikkaji
J554.832B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,4
Polarare Oberfläche (TPSA)
118 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
3
Schwere Atome
39
Formalladung
0
Komplexität
1.130

Physikochemische Eigenschaften

Schmelzpunkt
221 · 221-222 °C
Siedepunkt
859.1 · 859.1±65.0 °C(Predicted)
Dichte
1.45 · 1.45±0.1 g/cm3(Predicted)
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
pka
9.61 · 9.61±0.60(Predicted)
Farbe
Light Beige to Dark Brown
Stabilität
Hygroscopic, Unstable in solution

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Health EffectsIngestion 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)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary · 1 Eintrag

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. (A2914, A2915, A2916)

Signs and Symptoms · 1 Eintrag

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)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationDrugs used to cause constriction of the blood vessels.

Verwendung und Herstellung

UsesErgovaline is an ergopeptine and alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. (L1918)
Anwendungen · 1 Eintrag

VerwendenErgovaline is an ergopetine alkaloid commonly found in endophyte-infected species of tall grass fescue. Ergovaline is known to cause tall fescue toxicosis and is toxic to cattle feeding on the infected grass as it inhibits vesicular glutamate transporter activity in cow cerebral synatic vesicles.

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