Dopaminhydrochlorid
DOPAMINE HYDROCHLORIDE · 3-HYDROXYTYRAMINE HYDROCHLORIDE · DOPAMINE HCL · 2-benzenediol,4-(2-aminoethyl)-hydrochloride · 2-(3,4-DIHYDROXYPHENYL)ETHYLAMINE HYDROCHLORIDE · ASL-279 · intropin · Dopamin Hcl
Identifikatoren & physikalische Daten
| CAS No. | 62-31-7 |
|---|---|
| Summenformel | C8H12ClNO2 |
| Durchschnittliche Molmasse | 189,64 g/mol |
| Monoisotopische Masse | 189,0556563 g/mol |
| SMILES | Cl.NCCc1ccc(O)c(O)c1 |
| InChIKey | CTENFNNZBMHDDG-UHFFFAOYSA-N |
| PubChem CID | 65340 |
| ChEMBL | CHEMBL1557 |
| ChEBI | CHEBI:4698 |
| EC No. | 200-527-8 |
| DTXSID | DTXSID7020550 |
| Lokaler Name | Dopaminhydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 66,5 |
|---|---|
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 119 |
| Human Drugs | FDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 248-250 °C(lit.) |
| Dichte | 1.4 g/cm3 |
| Flammpunkt | 11℃ |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | alcohol: 20 mg/mLsoluble |
| Aggregatzustand | Crystalline Powder |
| Farbe | light tan |
| Merck | 14,8462 |
| BRN | 3656720 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. Combustible. |
| Hauptanwendungen | pharmaceutical (small molecule) |
| InChI | 1S/C8H11NO2.ClH/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 |
| InChIKey | CTENFNNZBMHDDG-UHFFFAOYSA-N |
| SMILES | Cl[H].NCCc1ccc(O)c(O)c1 |
| CAS Datenbank | 62-31-7(CAS DataBase Reference) |
| EPA chemische Informationen | 1,2-Benzenediol, 4-(2-aminoethyl)-, hydrochloride (62-31-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (84.3%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Dopamine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,2-Benzenediol, 4-(2-aminoethyl)-, hydrochloride: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (84.3%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Dopamine hydrochloridevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| F | 8-10-23 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN1230 - class 3 - PG 2 - Methanol, solution |
| Zollcode | 29222900 |
| RTECS-Nr. | UX1092000 |
| R-Sätze (R) | 36/37/38-50/53-22-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 orally in Rabbit: 2859 mg/kg |
| Gefahrensymbole | Xi,N,Xn,T,F |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36-61-45-36/37-16 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Skin Sens. 1 |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
Endogenous catecholamine with α and β-adrenergic activity. Cardiotonic; antihypotensive.
Herstellung & Synthese
synthetische
Dopamine hydrochloride is produced through the ring-opening reaction of piperonyl ethylamine. Piperethylamine and phenol are added to a reaction vessel and cooled down. Hydrochloric acid is slowly added while heating up the mixture to 110°C, and refluxed for 12-44 hours until the reaction reaches completion. The solution is then slightly cooled and water is added, and the mixture is stirred well and allowed to separate into layers. The upper phenolic layer is then removed, and the aqueous layer is extracted with isopropyl acetate. The extracted aqueous layer is then evaporated under reduced pressure (8.0kPa) until dry. Half the amount of ethanol and hydrochloric acid are added to the dry residue and heated to dissolve. The solution is then cooled, crystallized, and filtered. The filter cake is washed with ethanol and dried to obtain the final product, with a yield of 74%.