Dopamine

Base Information

• Chemical Name: Dopamine
• CAS No.: 51-61-6
• Molecular Formula: C8H11NO2
• Molecular Weight: 153.181
• European Community (EC) Number: 200-110-0
• NSC Number: 173182
• UNII: VTD58H1Z2X
• DSSTox Substance ID: DTXSID6022420
• Nikkaji Number: J4.120C,J968.027F
• Wikipedia: Dopamine
• Wikidata: Q170304
• NCI Thesaurus Code: C62025
• RXCUI: 3628
• Pharos Ligand ID: 6642Z5HPHSM5
• Metabolomics Workbench ID: 37060
• ChEMBL ID: CHEMBL59
• Mol file: 51-61-6.mol

Synonyms:3,4 Dihydroxyphenethylamine;3,4-Dihydroxyphenethylamine;4-(2-Aminoethyl)-1,2-benzenediol;Dopamine;Dopamine Hydrochloride;Hydrochloride, Dopamine;Hydroxytyramine;Intropin

Chemical Property of Dopamine

Chemical Property:

• Vapor Pressure: 5.27E-05mmHg at 25°C
• Melting Point: 218-220 oC
• Refractive Index: 1.4770 (estimate)
• Boiling Point: 337.69 °C at 760 mmHg
• PKA: 8.9(at 25℃)
• Flash Point: 158.03 °C
• PSA: 66.48000
• Density: 1.248 g/cm³
• LogP: 1.29930
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 153.078978594
• Heavy Atom Count: 11
• Complexity: 119

Purity/Quality:

99.0% ^*data from raw suppliers

Dopamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCN)O)O
• Recent ClinicalTrials: The Effect of Dopamine on Pulmonary Diffusion and Capillary Blood Volume During Exercise
• Recent EU Clinical Trials: A new concept of continuous dopaminergic stimulation by cerebroventricular administration of A-dopamine (dopamine stored in anaerobia) for severe motor fluctuations in Parkinson’s disease?
• Recent NIPH Clinical Trials: The effectiveness of motor and psychiatric symptoms for Parkinson's disease patients by switching from Dopamine agonist to Zonisamide or combining Dopamine agonist and Zonisamide.
• Description: Dopamine, abbreviated DA, is a biosynthetic compound and neurotransmitter produced in the body from the amino acid tyrosine by several pathways. It is synthesized in the adrenal gland where it is a precursor to other hormones (see Epinephrine) and in several portions of the brain, principally the substantia nigra and hypothalamus.
• Uses: Dopamine(3-Hydroxytyramine) is used as a drug to treat several conditions. It can be injected as a solution ofdopamine hydrochloride, such as in the drug Intropin. It is used as a stimulant to the heartmuscle to treat heart conditions; it also constricts the blood vessels, increasing systolic bloodpressure and improving blood flow through the body. Dopamine is used in renal medicationsto improve kidney function and urination. Dopamine dilates blood vessels in the kidneys,increasing the blood supply and promoting the fl ushing of wastes from the body. Dopamineis used to treat psychological disorders such as schizophrenia and paranoia. Adrenergic. Dopamine exhibits its primary action of the cardiovascular system, kidneys, and mesentery. It is used as a temporary agent for treating hypotension and circulatory shock caused by myocardial stroke, trauma, kidney rejection, and endogenous septicemia. The main indication for use of this drug is shock of various origins (cardiogenic, postoperational, infectious-toxic, anaphylactic), severe hypotension, and imminent renal insufficiency.
• Therapeutic Function: Cardiotonic
• Biological Functions: Quantitatively, dopamine is the most important of the biogenic amine neurotransmitters in the CNS.The three major distinct dopaminergic systems in the mammalian brain are categorized according to the lengths of the neurons. There is a system comprising ultrashort neurons within amacrine cells of the retina and periglomerular cells in the olfactory bulb. Of the several intermediate-length dopaminergic neuronal systems, the best studied are neurons in the tuberobasal ventral hypothalamus that innervate the median eminence and the intermediate lobe of the pituitary. These neurons are important in the regulation of various hypothalamohypophysial functions, including prolactin release from the anterior pituitary.The best-categorized of the dopamine neuronal systems are the long projections from nuclei in the substantia nigra and ventral tegmental areas to the limbic cortex; other limbic structures, including the amygdaloid complex and piriform cortex; and the neostriatum (primarily the caudate and putamen). In Parkinson’s disease, the primary biochemical feature is a marked reduction in the concentration of dopamine in this long projection system. Several classes of drugs, notably the antipsychotics, discussed in Chapter 34, interfere with dopaminergic transmission. In general, dopamine appears to be an inhibitory neurotransmitter. Five dopamine receptors have been identified; the most important and best studied are the D1- and D2-receptor groups.The D1-receptor, which increases cyclic adenosine monophosphate (cAMP) by activation of adenylyl cyclase, is located primarily in the region of the putamen, nucleus accumbens, and in the olfactory tubercle. The D2-receptor decreases cAMP, blocks certain calcium channels, and opens certain potassium channels.
• Clinical Use: Although not strictly an adrenergic drug, dopamine is a catecholamine with properties related to the cardiovascular activities of the other agents in this chapter. Dopamine acts on specific dopamine receptors to dilate renal vessels, increasing renal blood flow. Dopamine also stimulates cardiac β1-receptors through both direct and indirect mechanisms. It is used to correct hemodynamic imbalances induced by conditions such as shock, myocardial infarction, trauma, or congestive heart failure. As a catechol and primary amine, dopamine is rapidly metabolized by COMT and MAO and, similar to dobutamine, has a short duration of action with no oral activity. It is administered as an intravenous infusion.

Technology Process of Dopamine

There total 48 articles about Dopamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

levodopa (59-92-7,90638-38-3) → dopamine (51-61-6)

Guidance literature:

With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase; In various solvent(s); at 30 ℃; for 48h;

Reference yield:

2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin (76734-99-1) → dopamine (51-61-6) + arterenone (499-61-6) + 2-hydroxy-3′,4′-dihydroxyacetophenone (29477-54-1)

Guidance literature:

With hydrogenchloride; at 110 ℃; for 3h;

DOI:10.1016/0040-4020(80)80172-4

Reference yield:

tyrosamine (51-67-2) → dopamine (51-61-6) + dopaminoquinone (50673-96-6)

Guidance literature:

With tyrosinase; In phosphate buffer; for 0.333333h; pH=6.3;

DOI:10.1002/chem.200700734

upstream raw materials:

levodopa

3-amino-4-hydroxyphenylethylamine

2-(3,4-dimethoxyphenyl)-ethylamine

(+/-)-salsolinol

Downstream raw materials:

1-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol

1-[2-(3,4-Dihydroxy-phenyl)-ethyl]-4-methyl-1,4-dihydro-pyridine-3,5-dicarbaldehyde

2,2,3,3,3-Pentafluoro-propionic acid 5-[2-(2,2,3,3,3-pentafluoro-propionylamino)-ethyl]-2-(2,2,3,3,3-pentafluoro-propionyloxy)-phenyl ester

dopaminoquinone

Refernces

• 1、 Zhao, Jiahui,Bao, Xingfu,Wang, Shuang,Lu, Shasha,Sun, Jian,Yang, Xiurong. "In Situ Fluorogenic and Chromogenic Reactions for the Sensitive Dual-Readout Assay of Tyrosinase Activity". . p. 10529 - 10536. Retrieved 2017.
• 2、 Gennari, Arianna,Gujral, Chirag,Hohn, Erwin,Lallana, Enrique,Cellesi, Francesco,Tirelli, Nicola. "Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation". . p. 1391 - 1402. Retrieved 2017.
• 3、 Chen, Jinxing,Dong, Shaojun,Fang, Youxing,Li, Minghua,Wu, Weiwei. "Oxidase-like MOF-818 Nanozyme with High Specificity for Catalysis of Catechol Oxidation". supporting information. p. 15569 - 15574. Retrieved 2020/10/18.
• 4、 Wang, Yu,Tappertzhofen, Nadine,Méndez-Sánchez, Daniel,Bawn, Maria,Lyu, Boyu,Ward, John M.,Hailes, Helen C.. "Design and Use of de novo Cascades for the Biosynthesis of New Benzylisoquinoline Alkaloids". supporting information. p. 10120 - 10125. Retrieved 2019/06/27.