Noradenalone hydrochloride

HCID 199831CAS 5090-29-9

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Basic information

Standard SMILES: Cl.NCC(=O)c1ccc(O)c(O)c1
InChIKey: ILTXTELYZNIJHL-UHFFFAOYSA-N
Molecular formula: C8H10ClNO3
Average molar mass: 203.62 g/mol
Monoisotopic mass: 203.03492086

Names & identifiers

Preferred name: Noradenalone hydrochloride
IUPAC: 2-amino-1-(3,4-dihydroxyphenyl)ethanone;hydrochloride
English name: 3,4-dihydroxy-α-aminoacetophenone hydrochloride
Molecular formula: C8H10ClNO3
Molecular weight: 203.6229

Names & synonyms

5090-29-9Noradenalone hydrochlorideDTXSID30198929RefChem:1092569DTXCID401214202-Amino-1-(3,4-dihydroxyphenyl)ethanone hydrochloride2-amino-1-(3,4-dihydroxyphenyl)ethanone,hydrochloride2-Amino-1-(3,4-dihydroxyphenyl)ethan-1-one hydrochlorideEthanone, 2-amino-1-(3,4-dihydroxyphenyl)-, hydrochloride2-amino-1-(3,4-dihydroxyphenyl)ethanone;hydrochlorideMFCD005226922-Amino-1-(3,4-dihydroxyphenyl)ethanone hydrochloride (Noradrenaline Impurity)

Show more names

Noradrenalone HydrochlorideNoradrenalone HClNORADRENALINE IMPURITY BNorepinephrine Impurity 1Carbazochrome Impurity 23NORADRENALONE HYDROCHLORIDYLNoradrenaline EP Impurity B HClSodium carbalosulfonate impurity 23

Noradrenalone-d5 HydrochlorideNorepinephrine EP Impurity B HClNorepinephrine EPImpurityB3,4-dihydroxy-|A-aminoacetophenone hydrochlorideorb3181224SCHEMBL7146837SCHEMBL31534576FAA09029

Database identifiers

CAS: 5090-29-9
PubChem CID: 199831
DTXSID: DTXSID30198929

Properties

Computed structural properties

Topological polar surface area: 83.6 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 172

Physicochemical properties

Melting point: 255 °C · 255 °C
storage temp.: -20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility: DMSO (Slightly, Heated), Water (Very Slightly, Heated)
form: Solid
color: Dark Yellow to Dark Brown
InChI: InChI=1S/C8H9NO3.ClH/c9-4-8(12)5-1-2-6(10)7(11)3-5;/h1-3,10-11H,4,9H2;1H
InChIKey: ILTXTELYZNIJHL-UHFFFAOYSA-N
SMILES: C(=O)(C1=CC=C(O)C(O)=C1)CN.[H]Cl

Chemistry & industry

Applications

UsesNoradrenalone Hydrochloride is an intermediate of Norepinephrine (N674500), an antagonist of dibutyryl cyclic AMP in the regulation of narcosis. Norepinephrine modulates human dendritic cell activation by altering cytokine release.

Preparation methods

PreparationPreparation by demethylation of a-amino-3,4-dimethoxy-acetophenone on heating with 37% hydrochloric acid for 2.5 h at 160–165° under carbon dioxide (85%).