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エルゴバリン

Ergovaline

HCID 104843
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
2873-38-3
標準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
分子式
C29H35N5O5
平均分子量
533.6 g/mol
単同位体質量
533.26381923

概要

Ergovaline is a peptide ergot alkaloid.

名称と識別子

優先名称
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
現地名
エルゴバリン
英語名
ergovaline
分子式
C29H35N5O5
分子量
533.62

名称と別名

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
名称をさらに表示
エルゴバリン12′-ヒドロキシ-2′-メチル-5′α-イソプロピルエルゴタマン-3′,6′,18-トリオンaci-エルゴバリン(4R,7R)-N-[(1S,2S,4R,7S)-2-ヒドロキシ-4-メチル-5,8-ジオキソ-7-(プロパン-2-イル)-3-オキサ-6,9-ジアザトリシクロ[7.3.0.02,6]ドデカン-4-イル]-6-メチル-6,11-ジアザテトラシクロ[7.6.1.02,7.012,16]ヘキサデカ-1(16),2,9,12,14-ペンタエン-4-カルボキサミド

物性

構造計算による物性

XLogP
1.4
極性表面積
118 Ų
水素結合供与体数
3
水素結合受容体数
6
回転可能結合数
3
重原子数
39
形式電荷
0
複雑度
1,130

物理化学的性質

融点
221 · 221-222 °C
沸点
859.1 · 859.1±65.0 °C(Predicted)
比重(密度)
1.45 · 1.45±0.1 g/cm3(Predicted)
溶解性
Chloroform (Slightly), Methanol (Slightly)
外見
Solid
酸解離定数(Pka)
9.61 · 9.61±0.60(Predicted)
色
Light Beige to Dark Brown
安定性
Hygroscopic, Unstable in solution

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

毒性情報

Treatment · 1 件

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 件

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 件

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 Classification

化学と産業

薬理情報

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

用途と製造

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)
応用分野 · 1 件

使用Ergovaline 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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化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
Brexpiprazole Impurity 96
Ergotaman-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

データベース識別子

CAS
2873-38-3
PubChem CID
104843
DTXSID
DTXSID10893243
ChEBI
CHEBI:184047
UNII
059E2O9IV4
Nikkaji
J554.832B
No indication of carcinogenicity to humans (not listed by IARC).
深圳聚合生化科技有限公司
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