α-(1-アミノエチル)ベンジルアルコール
(1S,2R)-(+)-Norephedrine
基本情報
- CAS
14838-15-4- 標準SMILES
CC(N)C(O)c1ccccc1- InChIKey
DLNKOYKMWOXYQA-UHFFFAOYSA-N- 分子式
- C9H13NO
- 平均分子量
- 151.21 g/mol
- 単同位体質量
- 151.09971404
概要
Phenylpropanolamine is a sympathomimetic agent that acts as a nonselective adrenergic receptor agonist and norepinephrine reuptake inhibitor. It has been used as a decongestant and appetite suppressant. Currently, it is withdrawn from the market in Canada and the United States due to the risk for hemorrahgic strokes.
名称と識別子
- 優先名称
- (1S,2R)-(+)-Norephedrine
- IUPAC
- 2-amino-1-phenylpropan-1-ol
- 現地名
- α-(1-アミノエチル)ベンジルアルコール
- 英語名
- Benzenemethanol, -alpha--(1-aminoethyl)-
- 分子式
- C9H13NO
- 分子量
- 151.21
名称と別名
2-Amino-1-phenyl-1-propanol(1S,2R)-(+)-NorephedrineDTXSID70859305RefChem:393928DTXCID00196755628-077-148115-38-4alpha-(1-aminoethyl)benzyl alcoholNSC-120735UNII-683H0R96592-Amino-2-methyl-1-phenylethanol2-Amino-1-hydroxy-1-phenylpropane
名称をさらに表示
α-メチル-β-ヒドロキシベンゼンエタンアミンノルエフェドリン2-アミノ-1-フェニル-1-プロパノールα-(1-アミノエチル)ベンゼンメタノールα-(1-アミノエチル)ベンジルアルコール1-フェニル-2-アミノ-1-プロパノール2-アミノ-1-フェニルプロパン-1-オールα-(1-Aminoethyl)benzenemethanolBenzenemethanol, α-(1-aminoethyl)-Benzenemethanol, -alpha--(1-aminoethyl)-
beta-Hydroxy-alpha-methylphenethylamineBenzenemethanol, alpha-(1-aminoethyl)-Benzenemethanol, .alpha.-(1-aminoethyl)-683H0R965937577-28-9Dexatrim(-)-Pseudo NorephedrineNorpseudoephedrine, (+)-
データベース識別子
- CAS
14838-15-4、37577-28-9、48115-38-4- PubChem CID
- 4786
- DTXSID
DTXSID70859305- ChEMBL
CHEMBL61006- EC Number
- 628-077-1
- Nikkaji
- J136.573H
物性
構造計算による物性
- XLogP
- 0.8
- 極性表面積
- 46.3 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 2
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 110
実験および物理化学的性質
Drugs
DEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (S)
Pharmaceuticals
SolubilityFreely soluble
Melting Point190-194 °C
Dissociation Constants9.44 (at 20 °C)
物理化学的性質
- 融点
- 103 °C · 103 °C
- 沸点
- 122 °C · 122 °C(Press: 4-5 Torr)
- 比重(密度)
- 1.071 · 1.071±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 12.07 · 12.07±0.45(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。
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 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%)
化学と産業
薬理情報
Pharmacodynamics
Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.
Mechanism of Action
Phenylpropanolamine acts directly on alpha- and, to a lesser degree, beta-adrenergic receptors in the mucosa of the respiratory tract. Stimulation of alpha-adrenergic receptors produces vasoconstriction, reduces tissue hyperemia, edema, and nasal congestion, and increases nasal airway patency. PPA indirectly stimulates beta-receptors, producing tachycardia and a positive inotropic effect.
Biological Half-Life2.1 to 3.4 hours.
Metabolism/MetabolitesHepatic
Absorption, Distribution and ExcretionReduced bioavailability (about 38%) from gastrointestinal tract because of first pass metabolism by monoamine oxidase in the stomach and liver.
用途と製造
UsesUse (kg; approx.) in Germany (2009): >100
上流・下流製品情報
下流製品
関連反応
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