1,2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-
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Basic information
- CAS
138-65-8- Standard SMILES
NCC(O)c1ccc(O)c(O)c1- InChIKey
SFLSHLFXELFNJZ-UHFFFAOYSA-N- Molecular formula
- C8H11NO3
- Average molar mass
- 169.18 g/mol
- Monoisotopic mass
- 169.07389321
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
Properties
Computed structural propertiesFilling in
- XLogP
- -1.2
- Topological polar surface area
- 86.7 Ų
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
Chemistry & industry
Applications
Uses(±)-Noradrenaline is the neurotransmitter at most sympathetic neuroeffector junctions and has pharmacologic effects on both α1 and β1 adrenoceptors.
Additional notes
DefinitionChEBI: A catecholamine in which C-1 of the aminoethyl side-chain is hydroxy-substituted.
Related reactions
14 records
Compound notes
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