Dopamine

Base Information

• Chemical Name: Dopamine
• CAS No.: 62-31-7
• Molecular Formula: C8H12ClNO2
• Molecular Weight: 189.642
• Hs Code.: 29222900
• 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: 62-31-7.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:

• Appearance/Colour: off-white crystals
• Melting Point: 248-250 °C(lit.)
• Boiling Point: 337.7 °C at 760 mmHg
• Flash Point: 158 °C
• PSA: 66.48000
• Density: 1.4 g/cm3
• LogP: 2.10130
• Storage Temp.: Store at -20°C
• Sensitive.: Air & Light Sensitive
• Solubility.: alcohol: 20 mg/mL
• Water Solubility.: soluble
• 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%, ^*data from raw suppliers

Dopamine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,Xn,T,F
• Statements: 36/37/38-50/53-22-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-61-45-36/37-16

MSDS Files:

SDS file from LookChem

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 (hydrochloride) is an endogenous catecholamine neurotransmitter synthesized from the amino acid L-tyrosine that acts as an agonist at dopamine receptors (D1-5). Dopamine is mainly synthesized in the substantia nigra and ventral tegmental area, and is a precursor in norepinephrine and epinephrine biosynthesis. Dopamine-containing neurons in the brain are involved in reward-motivated behavior, motor control, and hormone release. Dopamine is also synthesized in the adrenal glands where it exerts peripheral paracrine functions including control of vasodilation, sodium excretion, insulin production, gastrointestinal motility, and the activity of lymphocytes. Loss or damage of dopaminergic neurons in the substantia nigra is associated with Parkinson’s disease.
• Uses: Endogenous catecholamine with α and β-adrenergic activity. Cardiotonic; antihypotensive. dopaminergic: Dopamine (DA) works as neurotransmitter in the central nervous system. It is a catecholamine made from the amino acid L-tyrosine. It also works as a hormone in vesicles of the adrenal medulla, thereby controlling heart beat rate and blood pressure. Absence of DA-containing neurons is associated with parkinson′s disease. A neurotransmitter and vasopressor that modulates cortical activation. Dopamine hydrochloride is a vasopressor that moderates cortical activation. It is used as a precursor to norepinepherine and epinephrine. It is an important neurotransmitter and chemical messenger that helps in the transmission of signals in the brain and other vital areas.
• Indications: Dopamine HCl is indicated 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.
• Clinical Use: Cardiogenic shock in infarction or cardiac surgery
• Drug interactions: Potentially hazardous interactions with other drugsAlpha-blockers: avoid with tolazoline.Anaesthetics: risk of ventricular arrhythmias with isoflurane - avoid.Antidepressants: risk of hypertensive crisis with MAOIs and moclobemide.Ciclosporin: may reduce risk of ciclosporin nephrotoxicityDopaminergics: effects possibly enhanced by entacapone; avoid with rasagiline; risk of hypertensive crisis with selegiline.

Technology Process of Dopamine

There total 13 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: 100.0%

N-(tert-butoxycarbonyl)dopamine (37034-31-4) → dopamine hydrochloride (62-31-7)

Guidance literature:

With methanol; chloro-trimethyl-silane; for 3h; Reflux;

DOI:10.1055/s-0029-1217027

Reference yield: 99.0%

3,4-bis(benzyloxy)-β-nitrostyrene (1699-54-3) → dopamine hydrochloride (62-31-7)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 24h; under 760 Torr; Ambient temperature;

DOI:10.1246/bcsj.63.1252

Reference yield: 98.6%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) → dopamine hydrochloride (62-31-7)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 160 ℃; for 6h; Inert atmosphere;

upstream raw materials:

3,4-bis(benzyloxy)-β-nitrostyrene

2-(3,4-dimethoxyphenyl)-ethylamine

N-(N-acetyl-L-methionyl)-O,O-bis(ethoxycarbonyl)dopamine

N-(tert-butoxycarbonyl)dopamine

Downstream raw materials:

1-phenyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid

5-S-cysteinyldopamine

6-<(2-amino-2-carboxyethyl)thio>-7-(2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid

Refernces

• 1、 -. "Synthetic method of high-purity dopamine hydrochloride". . . Retrieved 2020/11/23.
• 2、 Boyington, Allyson J.,Seath, Ciaran P.,Zearfoss, Avery M.,Xu, Zihao,Jui, Nathan T.. "Catalytic Strategy for Regioselective Arylethylamine Synthesis". supporting information. p. 4147 - 4153. Retrieved 2019/03/07.