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8,9-ジデヒドロ-6,8-ジメチルエルゴリン

(-)-Agroclavine

HCID 73484
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
548-42-5
標準SMILES
CC1=C[C@@H]2c3cccc4[nH]cc(c34)C[C@H]2N(C)C1
InChIKey
XJOOMMHNYOJWCZ-UKRRQHHQSA-N
分子式
C16H18N2
平均分子量
238.33 g/mol
単同位体質量
238.14699858

概要

Agroclavine is an ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8. It is a conjugate base of an agroclavine(1+).

名称と識別子

優先名称
(-)-Agroclavine
IUPAC
(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinoline
現地名
8,9-ジデヒドロ-6,8-ジメチルエルゴリン
英語名
AGROCLAVINE
分子式
C16H18N2
分子量
238.33

名称と別名

Agroclavine548-42-5(-)-agroclavineA8SW57GO7TCHEBI:2519NSC-93132(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo[4,3-fg]quinolineagroclavine-1(6aR,10aR)-7,9-dimethyl-6,6a,8,10a-tetrahydro-4H-indolo(4,3-fg)quinolineRefChem:110218208-947-34,6-dimethyl-6,11-diazatetracyclo(7.6.1.02,7.012,16)hexadeca-1(16),3,9,12,14-pentaene
名称をさらに表示
アグロクラビン8,9-ジデヒドロ-6,8-ジメチルエルゴリン6,8-ジメチル-8,9-ジデヒドロエルゴリン(2R,7R)-4,6-ジメチル-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),3,9,12,14-ペンタエンNSC 93132agoclavine8,9-didehydro-6,8-dimethyl-ergolinERGOLINE,8,9-DIDEHYDRO-6,8-DIMETHYL-
8,9-Didehydro-6,8-dimethylergolineErgoline, 8,9-didehydro-6,8-dimethyl-(5R,10R)-agroclavineAGROCLAVINCHEMBL449081NSC93132(6aR,10aR)-7,9-dimethyl-4,6,6a,7,8,10a-hexahydroindolo[4,3-fg]quinolineCCRIS 2099

データベース識別子

物性

構造計算による物性

XLogP
2.6
極性表面積
19 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
0
重原子数
18
形式電荷
0
複雑度
375

実験および物理化学的性質

DrugsPharmaceuticals -> Antibiotics

物理化学的性質

融点
198 · 198-208℃ (decomposition) (ethyl ether )
比旋光度
20 · D20 -155° (c = 0.9 in chloroform); D20 -182° (c = 0.5 in pyridine)
沸点
370.93 °C · 370.93°C (rough estimate)
比重(密度)
0.9597 · 0.9597 (rough estimate)
屈折率
1.5 · 1.5000 (estimate)
貯蔵温度
Refrigerator, under inert atmosphere
溶解性
クロロホルム(微量)、メタノール(微量)
外見
個体
酸解離定数(Pka)
17.49 · 17.49±0.40(Predicted)
色
ペールベージュ

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。

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (100%)

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)

化学と産業

用途と製造

UsesAgroclavine is a naturally occuring 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)

調製方法

純化方法It crystallises from diethyl ether or Me2CO. The hydrochloride crystallises from H2O and has m 265-266o, [] 20 -110o (CHCl3). [Plieninger et al. Justus Liebigs Ann Chem 743 95 1971,Beilstein 23 III/IV 1623.]

上流・下流製品情報

上流原料

rac-(Z)-2-メチル-3-[(1,3,4,5-テトラヒドロ-4β*-(メチルアミノ)ベンゾ[cd]インドール)-5α*-イル]-2-プロペン-1-オール2-Propenal, 2-methyl-3-[(4R,5R)-1,3,4,5-tetrahydro-4-(methylamino)benz[cd]indol-5-yl]-, (2E)-インドール-3-カルボキシアルデヒド

サプライヤー9 社

艾吉析科技(上海)有限公司17717235263 · [email protected]
中梦研(湖北)科技有限公司0717-6300888 18062399888 · [email protected]

関連反応

3 件
反応記録を作成
HRID 231699 の反応式
HRID 231699生成物としてuspto-grants-1989_07
HRID 569317 の反応式
HRID 569317生成物としてuspto-grants-1988_03
HRID 2413902 の反応式
HRID 2413902反応物としてuspto-grants-1988_01

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
CAS
548-42-5
PubChem CID
73484
ChEMBL
CHEMBL449081
ChEBI
CHEBI:2519
UNII
A8SW57GO7T
EC Number
208-947-3
Nikkaji
J6.445I
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 ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

安全データ

risk_code
20/21/22
hazard_code
Xn
safety_code
36
Sinco Pharmachem (ShenZhen) R&D Co., Ltd.
+86-18603013401 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]

補足説明

定義ChEBI: An ergot alkaloid that is ergoline which contains a double bond between positions 8 and 9, and which is substituted by methyl groups at positions 6 and 8.