4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

• ChemBase编号: 252
• 分子式: C8H11NO3
• 平均质量: 169.17784
• 单一同位素质量: 169.07389322
• SMILES: O[C@H](c1cc(O)c(O)cc1)CN
• Canonical SMILES: NC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
• InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N

名称和登记号

名称

• IUPAC标准名: 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• IUPAC传统名: norepinephrine
• 商标名: Levophed
• 别名: L-去甲肾上腺素; L-Noradrenaline; 4-[(1R)-2-Amino-1-hydroxyethyl]benzene-1,2-diol; (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; L-Arterenol; Levarterenol; (-)-Norepinephrine; (R)-(–)-Norepinephrine; l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol; L-noradrenaline; Arterenol; L-Norepinephrine; Norepinephrine; Noradrenaline; Norepinephrine

登记号

• CAS号: 51-41-2(l); 51-41-2; 138-65-8
• EC号: 200-096-6
• MDL号: MFCD00025592
• Beilstein号: 2804840; 4231961
• 默克索引号: 146695
• PubChem SID: 24891196; 46506201; 160963715
• PubChem CID: 439260
• CHEBI ID: 18357
• ATC码: C01CA03
• CHEMBL: 1437
• Chemspider ID: 388394
• DrugBank ID: DB00368
• KEGG ID: D00076
• 维基百科标题: Norepinephrine

理论计算性质

JChem

• Acid pKa: 9.500885
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -3.0654356
• LogD (pH = 7.4): -1.8244592
• Log P: -0.6835134
• 摩尔折射率: 44.4557 cm^3
• 极化性: 17.37873 Å^3
• 极化表面积: 86.71 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.4
• LOG S: -1.13
• 溶解度: 1.25e+01 g/l

分子性质

理化性质

• 溶解度: 338 mg/mL [Predicted by ALOGPS]
• 外观: off-white to tan crystalline
• 熔点: ca 220°C dec.; L: 216.5–218 °C (decomp.); D/L: 191 °C (decomp.)
• 沸点: 442.6±40.0 °C (760 Torr)
• 密度: 1.397±0.06 g/cm^3 (20 °C and 760 Torr)
• 蒸汽压: 1.30e-8 Torr
• 比旋光度: [α]20/D -45±3°, c = 5% in 1 M HCl; -45 (c=5 in 0.5N HCl)
• 疏水性(logP): 0.2
• pKa: 9.57±0.10

安全信息

• 保存注意事项: Air & Light Sensitive; IRRITANT
• RTECS编号: DN5950000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+); X
• 联合国危险货物编号: 2811; UN2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 2; II
• 危险公开号: 20/21/22; 26/27/28
• 安全公开号: 28-36/37-45; 9-36/37
• TSCA收录: false; 否
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H300; H300-H310-H330
• GHS警示性声明: P260-P264-P280-P284-P302 + P350-P310; P264-P270-P301+P310-P321-P405-P501A
• 个人保护装置: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: -20°C; 2-8°C

药理学性质

• 相关基因信息: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)rat ... Adra1a(29412), Adra1d(29413), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318)

产品相关信息

• 纯度: ≥98%; ≥98.0% (sum of enantiomers, HPLC); 95+%; 98%
• Empirical Formula (Hill Notation): C8H11NO3

详细说明

DrugBank - DB00368

• Drug Groups: approved
• Description: Precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. [PubChem]
• Indication: Mainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Also used as a vasopressor medication for patients with critical hypotension.
• Pharmacology: Noradrenaline acts on both alpha-1 and alpha-2 adrenergic receptors to cause vasoconstriction. Its effect in-vitro is often limited to the increasing of blood pressure through antagonising alpha-1 and alpha-2 receptors and causing a resultant increase in systemic vascular resistance.
• Toxicity: In high dose and especially when it is combined with other vasopressors, it can lead to limb ischemia and limb death.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A7257

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Adrenergic neurotransmitter
Application
Norepinephrine is an adrenergic neurotransmitter used in the treatment of hypotension, depression, schizophrenia, and attention deficit/hyperactivity disorders.