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

• ChemBase ID: 862
• Molecular Formular: C8H11NO2
• Molecular Mass: 153.17844
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(2-aminoethyl)benzene-1,2-diol
• IUPAC Traditional name: dopamine
• Brand Name: Intropin; Revimine
• Synonyms: 2-(3,4-dihydroxyphenyl)ethylamine3,4-dihydroxyphenethylamine3-hydroxytyramine; DA; Intropin; Revivan; Oxytyramine; DA; Deoxyepinephrine; Dopamin; Dopamine HCl; Hydroxytyramine; Hydroxytyramin; Dophamine; Oxytyramine; Dopamine

Database IDs

• CAS Number: 51-61-6
• PubChem SID: 46506043; 160964325
• PubChem CID: 681
• CHEBI ID: 18243
• ATC CODE: C01CA04
• CHEMBL: 59
• Chemspider ID: 661
• DrugBank ID: DB00988
• KEGG ID: D07870
• Unique Ingredient Identifier: VTD58H1Z2X
• Wikipedia Title: Dopamine

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.007776
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.2235985
• LogD (pH = 7.4): -1.4458275
• Log P: 0.02955024
• Molar Refractivity: 43.2482 cm^3
• Polarizability: 16.667273 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.4
• LOG S: -1.31
• Solubility (Water): 7.43e+00 g/l

PROPERTIES

Physical Property

• Solubility: 60.0 g/100 ml in water; 600 g/L
• Apperance: colorless solid
• Melting Point: 128°C
• Boiling Point: decomposes
• Density: 1.26 g/cm^3
• Hydrophobicity(logP): 0.9

Safety Information

• Risk Statements: R36/37/38
• Safety Statements: S26 S36

DETAILS

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

REFERENCES

• 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