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(R)-α-(ヒドロキシメチル)ベンゼン酢酸(1R,5S)-トロパン-3α-イル

((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoate

HCID 637577
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
13269-35-7
標準SMILES
CN1[C@@H]2CC[C@H]1CC(OC(=O)[C@@H](CO)c1ccccc1)C2
InChIKey
RKUNBYITZUJHSG-JJXSEGSLSA-N
分子式
C17H23NO3
平均分子量
289.4 g/mol
単同位体質量
289.1677936

概要

(R)-atropine is an atropine with a 2R-configuration. It is functionally related to a (R)-tropic acid.

名称と識別子

優先名称
((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoate
IUPAC
[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoate
現地名
(R)-α-(ヒドロキシメチル)ベンゼン酢酸(1R,5S)-トロパン-3α-イル
英語名
R-(+)-Hyoscyamine
分子式
C17H23NO3
分子量
289.38

名称と別名

RefChem:1048825((1S,5R)-8-Methyl-8-Azabicyclo(3.2.1)Octan-3-Yl) (2R)-3-Hydroxy-2-Phenylpropanoated-hyoscyamine(+)-HYOSCYAMINE13269-35-7(+)-Atropine(R)-atropineR-(+)-HyoscyamineHyoscyamine, (+)-CHEMBL3084476V3203SI72Mhyoscyamine
名称をさらに表示
(+)-アトロピンd-ヒオスシアミン(1R,5S)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3α-オール(R)-α-(ヒドロキシメチル)ベンゼンアセタート(αR)-α-ヒドロキシメチルベンゼン酢酸(1β,5β)-8-メチル-8-アザビシクロ[3.2.1]オクタ-3α-イル(R)-α-(ヒドロキシメチル)ベンゼン酢酸(1R,5S)-トロパン-3α-イル(R)-α-(ヒドロキシメチル)ベンゼン酢酸(1β,5β)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3α-イル(αR)-α-(ヒドロキシメチル)ベンゼン酢酸(1R,5S)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3α-イル(+)-ヒオスシアミン(αR)-α-(ヒドロキシメチル)ベンゼン酢酸(1β,5β)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3α-イル(R)-α-(ヒドロキシメチル)ベンゼン酢酸(1R,5S)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3α-イル[(1α,5α)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3β-イル]=(R)-α-(ヒドロキシメチル)フェニルアセタート(1R,5S)-8-メチル-8-アザビシクロ[3.2.1]オクタン-3-イル (2R)-3-ヒドロキシ-2-フェニルプロパノアート

物性

構造計算による物性

XLogP
1.8
極性表面積
49.8 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
5
重原子数
21
形式電荷
0
複雑度
353

実験および物理化学的性質

Drugs · 2 件

DEA NFLIS-Drug Category -> Hallucinogens

Pharmaceuticals -> Listed in ZINC15

Color/FormNEEDLES FROM DIL ALCOHOL
SolubilitySLIGHTLY SOL IN WATER; VERY SOL IN ALCOHOL, ETHER, BENZENE, CHLOROFORM
Melting Point106 °C
Optical RotationSPECIFIC OPTICAL ROTATION (C= 4): +31.3 DEG/D

物理化学的性質

融点
106 °C · 106 °C
沸点
429.8 · 429.8±45.0 °C(Predicted)
比重(密度)
1.19 · 1.19±0.1 g/cm3(Predicted)
酸解離定数(Pka)
14.12 · 14.12±0.10(Predicted)

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

InteractionsLOW CONCN OF (+)-HYOSCYAMINE, ACCELERATED THE ENZYMIC HYDROLYSIS OF TROPACOCAINE, WHEREAS HIGHER CONCN ABOVE 10-4 TO 10-3 MOLE/L OF THESE ALKALOIDS INHIBITED THE HYDROLYSIS. HYDROLYSIS OF NORTROPACOCAINE WAS INHIBITED AT ALL CONCN.
Health EffectsHyoscyamine affects the central nervous system. (L1255)
Exposure RoutesOral (ingestion) (L1817) ; dermal (L1817)
Toxicity SummaryHyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system. (L1255)
Signs and Symptoms · 1 件

Side effects of hyoscyamine include dry mouth and throat, eye pain, blurred vision, restlessness, dizziness, arrythmia, flushing, and faintness. An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. (L1255)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Non-Human Toxicity Excerpts · 1 件

AT THERAPEUTIC DOSAGES, THE ISOMERS DIFFER MARKEDLY IN POTENCY, BOTH PERIPHERALLY & CENTRALLY. AT TOXIC DOSES, THE ISOMERS ARE EQUALLY POTENT. IN MICE, THE LD50 IS 81 MG/KG FOR (+)-HYOSCYAMINE & 95 MG/KG FOR (-)-HYOSCYAMINE. THE ED50 (CONVULSIONS) IS THE SAME, 54 MG/KG, FOR BOTH ISOMERS IN THE MOUSE.

安全データ

有毒物質データの
13269-35-7(Hazardous Substances Data)

化学と産業

用途と製造

Uses · 1 件

Hyoscyamine is a plant toxin found in certain plants of the Solanaceae family, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), and deadly nightshade (Atropa belladonna). It is used as a drug to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in palliative care.(L1255)

General Manufacturing Information · 2 件

THE DEXTRO & LEVO ISOMERS DIFFER MARKEDLY IN POTENCY AT THERAPEUTIC CONCENTRATIONS, BOTH CENTRALLY & PERIPHERALLY. BOTH ISOMERS APPEAR TO HAVE EQUAL POTENCY AT TOXIC CONCENTRATIONS, HOWEVER.

LIVER HOMOGENATES OF RABBITS CONTAINING HYOSCYAMINE ACYLHYDROLASE HYDROLYZED HYOSCYAMINE TO TROPINE AND (-)-TROPIC ACID BUT DID NOT CLEAVE (+)-HYOSCYAMINE. BECAUSE OF THE STEREOSPECIFICITY OF THIS ENZYME, THE HYOSCYAMINE COMPONENT OF (+)-HYOSCYAMINE PREPN OBTAINED CHEMICALLY COULD BE DETECTED AND THE DEXTROROTATORY OPTICAL ANTIPODE COULD BE PREPARED IN THE PURE FORM.

応用分野

使用D-Hyoscyamine is similar to L-Hyoscyamine (H674300), a natural compound that has inhibitory activity against cholinesterases. D-Hyoscyamine can be synthesized from Atropine (A794630).

サプライヤー4 社

深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
广州佳途科技股份有限公司020-81960175-877 18933936954 · [email protected]
常州翔龙医药科技有限公司18661161657 · [email protected]

関連反応

0 件
反応記録を作成

現在のフィルター条件では反応記録がありません。

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
d-Atropine
Atropine Impurity 42
[(1α,5α)-8-Methyl-8-azabicyclo[3.2.1]octan-3β-yl]=(R)-α-(hydroxymethyl)phenylacetate
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]octane-3α-ol (R)-α-(hydroxymethyl)benzeneacetate
Benzeneacetic acid, α-(hydroxymethyl)-, 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, [3(R)-endo]-
Benzeneacetic acid, α-(hydroxymethyl)-, (3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (αR)-
[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2R)-3-hydroxy-2-phenylpropanoatetropan-3alpha-yl (2R)-3-hydroxy-2-phenylpropanoate(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl (2R)-3-hydroxy-2-phenylpropanoateAtropine sulfateAtropine CRSHyoscyamine (D)-Atropine Impurity 27HYOSCYAMINE, D-

データベース識別子

CAS
13269-35-7
PubChem CID
637577
DTXSID
DTXSID201045952
ChEMBL
CHEMBL1379091、CHEMBL3084476
ChEBI
CHEBI:48882
UNII
V3203SI72M
Nikkaji
J82.086E

補足説明

定義ChEBI: An atropine with a 2R-configuration.