4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• ChemBase编号: 73260
• 分子式: C9H13NO3
• 平均质量: 183.20442
• 单一同位素质量: 183.08954328
• SMILES: c1(c(ccc(c1)C(CNC)O)O)O
• Canonical SMILES: CNCC(c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3
• InChIKey: UCTWMZQNUQWSLP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC传统名: (+-)-adrenaline; DL-adrenaline
• 别名: (±)-3,4-二羟基-α-(甲基氨基)苯甲醇; 3,4-二羟基-α-甲胺甲基苄醇; 4-[1-羟基-2-(甲基氨基)乙基]-1,2-苯二酚; 消旋肾上腺素; (±)-肾上腺素; (±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; (±)-Adrenalin; 3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; DL-Adrenaline; (+/-)-3,4-Dihydroxy-α-[(methylamino)methyl]benzyl Alcohol; 1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol; Epirenamine; Racepinefrine; Racepinephrine; rac Epinephrine; DL-Adrenaline; 3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; DL-EPINEPHRINE; (±)-Epinephrine; 4-(1-Hydroxy-2-(MethylaMino)ethyl)benzene-1,2-diol

登记号

• CAS号: 329-65-7
• EC号: 206-347-6
• MDL号: MFCD00063027
• PubChem SID: 162038180; 24894424
• PubChem CID: 838

理论计算性质

• Acid pKa: 9.69426
• 质子受体: 4
• 质子供体: 4
• LogD (pH = 5.5): -2.8488538
• LogD (pH = 7.4): -1.6309718
• Log P: -0.42952928
• 摩尔折射率: 49.2303 cm^3
• 极化性: 19.213377 Å^3
• 极化表面积: 72.72 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Aqueous Acid; DMSO (hot)
• 外观: Brown Solid
• 熔点: 196-199°C; 197 °C (dec.)(lit.); 205-210°C (dec.)

安全信息

• 保存条件: -20°C; 2-8°C, Store Under Nitrogen, Protect from light; Refrigerator
• RTECS编号: DO2975000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 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
• 澳大利亚Hazchem: 2XE
• 危险公开号: 24-36/37/38; R:25
• 安全公开号: 26-36/37-45; S:28-36/37/39-45-53
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H311-H315-H319-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338-P312
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• 保存温度: 2-8°C

药理学性质

• 作用靶点: GPCR
• 相关基因信息: rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176)

产品相关信息

• 纯度: ≥95%; 95%; 98%
• 成盐信息: Free Base
• 线性分子式: (HO)2C6H3CH(CH2NHCH3)OH

详细说明

MP Biomedicals - 02151064

Crystalline

Selleck Chemicals - S2523

Biological Activity:
DL-Adrenaline is a hormone and a neurotransmitter secreted by the medulla of the adrenal glands. In medicine DL-Adrenaline is used chiefly as a stimulant in cardiac arrest, as a vasoconstrictor in shock, and as a bronchodilator and antispasmodic in bronchial asthma. DL-Adrenaline is found in small amounts in the body and is essential for maintaining cardiovascular homeostasis because of its ability to divert blood to tissues under stress. DL-Adrenaline acts by binding to a variety of adrenergic receptors. DL-Adrenaline is a nonselective agonist of all adrenergic receptors, including α1, α2, β1, β2, and β3 receptors. Epinephrine’s binding to these receptors triggers a number of metabolic changes. Binding to α-adrenergic receptors inhibits insulin secretion by the pancreas, stimulates glycogenolysis in the liver and muscle, and stimulates glycolysis in muscle. [1][2]References on DL-Adrenaline[1] http://en.wikipedia.org/wiki/Epinephrine, , [2] Am J Physiol. , 1982 Apr, 242(4):H593-601

Sigma Aldrich - E1635

Biochem/physiol Actions
肾上腺受体激动剂

Sigma Aldrich - 316741

Biochem/physiol Actions
肾上腺受体激动剂

Toronto Research Chemicals - E588585

Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.

参考文献

• Berecek KH et al. Am J Physiol. 1982 Apr;242(4):H593-601.
• Cucinotta, V., et al.: J. Pharm. Biomed. Anal., 37, 1009 (2005)
• Marin-Zamora, M., et al.: J. Agric. Food Chem., 55, 4569 (2005)
• Kao, B., et al.: J. Perinatol., 28, 205 (2005)