1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)- (HCID 951)

Overview

Noradrenaline is a catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted. It has a role as a human xenobiotic metabolite. It is a conjugate base of a noradrenaline(1+).

Names & identifiers

Preferred name: 1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-
IUPAC: 4-(2-amino-1-hydroxyethyl)benzene-1,2-diol
English name: DL-NORADRENALINE
Molecular formula: C8H11NO3
Molecular weight: 169.18

Names & synonyms

1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-586-17-4RefChem:411258622-681-9138-65-84-(2-amino-1-hydroxyethyl)benzene-1,2-dioldl-Noradrenalinedl-Norepinephrinedl-Arterenol(+/-)-noradrenalineNSC 294898Norepinephrine, DL-

Show more names

(S)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid(+)-Norepinephrin(±)-NoradrenalineDopamine Impurity 7Dopamine Impurity 32

(+/-)-norepinephrineLevarterenol;L-Noradrenaline[3H]NEK294OAI79VNSC294898NSC-2948984-(2-amino-1-hydroxy-ethyl)benzene-1,2-diolNoradrenalin, dl-

Database identifiers

CAS: 138-65-8、586-17-4
PubChem CID: 951
DTXSID: DTXSID20858964
ChEMBL: CHEMBL432
ChEBI: CHEBI:33569
UNII: K294OAI79V
EC Number: 205-337-9、622-681-9
Nikkaji: J28.478E

Properties

Computed structural properties

XLogP: -1.2
Topological polar surface area: 86.7 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 12
Formal charge: 0
Complexity: 142

Experimental & physicochemical properties

DrugsPharmaceuticals

Physicochemical properties

Melting point: 190 °C · ~190 °C (dec.)
Boiling point: 298.46 °C · 298.46°C (rough estimate)
Density: 1.2435 · 1.2435 (rough estimate)
refractive index: 1.51 · 1.5100 (estimate)
storage temp.: 2 · 2-8°C
solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
pka: 9.57 · 9.57±0.10(Predicted)
form: Solid
color: Pale Beige to Dark Brown
Merck: 6695 · 6695
Stability: Hygroscopic
InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2
InChIKey: SFLSHLFXELFNJZ-UHFFFAOYSA-N
SMILES: C1(O)=CC=C(C(O)CN)C=C1O
CAS DataBase Reference: 138 · 138-65-8
FDA UNII: 294 OAI79V · K294OAI79V
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301
Precautionary statements: 264 · P264-P270-P301+P310-P321-P330-P405-P501
Hazard Codes: T+
Risk Statements: 28 · 28-41-26/27/28
Safety Statements: 28 · 28-36/37/39-45-36/37
RIDADR: 2811 · UN 2811
WGK Germany: 3 · 3
RTECS: 6300000 · DN6300000
F: 8 · 8-10-23
HazardClass: IRRITANT
Toxicity: 50 ivn-rat: · LD50 ivn-rat: 130 mg/kg JPETAB 95,502,49
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (13.3%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P316, P301+P317, P305+P354+P338, P317, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 09-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/22124

Hazard Classes and CategoriesAcute Tox. 3 (13.3%)

Safety data

F: 8-10-23
wgk: 3
rtecs: DN6300000
ridadr: UN 2811
Toxicity: LD50 ivn-rat: 130 mg/kg JPETAB 95,502,49
risk_code: 28-41-26/27/28
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+
safety_code: 28-36/37/39-45-36/37
hazard_class: IRRITANT
Hazard statements: H301
REACH Registrations: Active
Precautionary statements: P264-P270-P301+P310-P321-P330-P405-P501

Chemistry & industry

Applications

Uses(±)-Noradrenaline is the neurotransmitter at most sympathetic neuroeffector junctions and has pharmacologic effects on both α1 and β1 adrenoceptors.