4-(2-aminoethyl)benzene-1,2-diol

• ChemBase编号: 862
• 分子式: C8H11NO2
• 平均质量: 153.17844
• 单一同位素质量: 153.0789786
• SMILES: Oc1cc(CCN)ccc1O
• Canonical SMILES: NCCc1ccc(c(c1)O)O
• InChI: InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
• InChIKey: VYFYYTLLBUKUHU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(2-aminoethyl)benzene-1,2-diol
• IUPAC传统名: dopamine
• 商标名: Intropin; Revimine
• 别名: 2-(3,4-dihydroxyphenyl)ethylamine3,4-dihydroxyphenethylamine3-hydroxytyramine; DA; Intropin; Revivan; Oxytyramine; DA; Deoxyepinephrine; Dopamin; Dopamine HCl; Hydroxytyramine; Hydroxytyramin; Dophamine; Oxytyramine; Dopamine

登记号

• CAS号: 51-61-6
• PubChem SID: 160964325; 46506043
• PubChem CID: 681
• CHEBI ID: 18243
• ATC码: C01CA04
• CHEMBL: 59
• Chemspider ID: 661
• DrugBank ID: DB00988
• KEGG ID: D07870
• 美国药典/FDA物质标识码: VTD58H1Z2X
• 维基百科标题: Dopamine

理论计算性质

JChem

• Acid pKa: 10.007776
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.2235985
• LogD (pH = 7.4): -1.4458275
• Log P: 0.02955024
• 摩尔折射率: 43.2482 cm^3
• 极化性: 16.667273 Å^3
• 极化表面积: 66.48 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: -0.4
• LOG S: -1.31
• 溶解度: 7.43e+00 g/l

分子性质

理化性质

• 溶解度: 60.0 g/100 ml in water; 600 g/L
• 外观: colorless solid
• 熔点: 128°C
• 沸点: decomposes
• 密度: 1.26 g/cm^3
• 疏水性(logP): 0.9

安全信息

• 危险公开号: R36/37/38
• 安全公开号: S26 S36

详细说明

DrugBank - DB00988

• Drug Groups: approved
• Description: One of the catecholamine neurotransmitters in the brain. It is derived from tyrosine and is the precursor to norepinephrine and epinephrine. Dopamine is a major transmitter in the extrapyramidal system of the brain, and important in regulating movement. A family of receptors (receptors, dopamine) mediate its action. [PubChem]
• Indication: For the correction of hemodynamic imbalances present in the shock syndrome due to myocardial infarction, trauma, endotoxic septicemia, open-heart surgery, renal failure, and chronic cardiac decompensation as in congestive failure
• Pharmacology: Dopamine is a natural catecholamine formed by the decarboxylation of 3,4-dihydroxyphenylalanine (DOPA). It is a precursor to norepinephrine in noradrenergic nerves and is also a neurotransmitter in certain areas of the central nervous system, especially in the nigrostriatal tract, and in a few peripheral sympathetic nerves. Dopamine produces positive chronotropic and inotropic effects on the myocardium, resulting in increased heart rate and cardiac contractility. This is accomplished directly by exerting an agonist action on beta-adrenoceptors and indirectly by causing release of norepinephrine from storage sites in sympathetic nerve endings.
• Toxicity: LD₅₀ oral mice = 1460 mg/kg, LD₅₀ oral rats = 1780 mg/kg. Spasm or closing of eyelids, nausea, vomiting, cardiac arrhythmias, involuntary movements of the body including the face, tongue, arms, hand, head, and upper body; hypotension, haemolytic anaemia, urinary retention, duodenal ulcer, sialorrhea, ataxia, abdominal pain, dry mouth, nightmares, tachypnoea, bruxism, confusion, and insomnia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Biotransformation of dopamine proceeds rapidly to yield the principal excretion products, 3-4-dihydroxy-phenylacetic acid (DOPAC) and 3-methoxy-4-hydroxy-phenylacetic acid (homovanillic acid, HVA).
• Absorption: Dopamine is rapidly absorbed from the small intestine.
• Half Life: 2 minutes
• Protein Binding: No information currently available on protein binding.
• Elimination: It has been reported that about 80% of the drug is excreted in the urine within 24 hours, primarily as HVA and its sulfate and glucuronide conjugates and as 3,4-dihydroxyphenylacetic acid.; A very small portion is excreted unchanged.
• References: Barron AB, Maleszka R, Vander Meer RK, Robinson GE: Octopamine modulates honey bee dance behavior. Proc Natl Acad Sci U S A. 2007 Jan 30;104(5):1703-7. Epub 2007 Jan 19. [Pubmed] ; Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. [Pubmed] ; Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. [Pubmed] ; Berridge KC, Robinson TE: What is the role of dopamine in reward: hedonic impact, reward learning, or incentive salience? Brain Res Brain Res Rev. 1998 Dec;28(3):309-69. [Pubmed] ; Pecina S, Cagniard B, Berridge KC, Aldridge JW, Zhuang X: Hyperdopaminergic mutant mice have higher "wanting" but not "liking" for sweet rewards. J Neurosci. 2003 Oct 15;23(28):9395-402. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Giuliano F, Allard J: Dopamine and male sexual function. Eur Urol. 2001 Dec;40(6):601-8. Pubmed
• Giuliano F, Allard J: Dopamine and sexual function. Int J Impot Res. 2001 Aug;13 Suppl 3:S18-28. Pubmed
• Barron AB, Maleszka R, Vander Meer RK, Robinson GE: Octopamine modulates honey bee dance behavior. Proc Natl Acad Sci U S A. 2007 Jan 30;104(5):1703-7. Epub 2007 Jan 19. Pubmed
• Berridge KC, Robinson TE: What is the role of dopamine in reward: hedonic impact, reward learning, or incentive salience? Brain Res Brain Res Rev. 1998 Dec;28(3):309-69. Pubmed
• Pecina S, Cagniard B, Berridge KC, Aldridge JW, Zhuang X: Hyperdopaminergic mutant mice have higher "wanting" but not "liking" for sweet rewards. J Neurosci. 2003 Oct 15;23(28):9395-402. Pubmed