4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol

• ChemBase ID: 252
• Molecular Formular: C8H11NO3
• Molecular Mass: 169.17784
• Monoisotopic Mass: 169.07389322
• SMILES: O[C@H](c1cc(O)c(O)cc1)CN
• Canonical SMILES: NC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
• InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol
• IUPAC Traditional name: norepinephrine
• Brand Name: Levophed
• Synonyms: L-Noradrenaline; 4-[(1R)-2-Amino-1-hydroxyethyl]benzene-1,2-diol; (R)-4-(2-Amino-1-hydroxyethyl)-1,2-benzenediol; L-Arterenol; Levarterenol; (-)-Norepinephrine; (R)-(–)-Norepinephrine; l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol; L-noradrenaline; Arterenol; L-Norepinephrine; Norepinephrine; Noradrenaline; Norepinephrine; L-去甲肾上腺素

Database IDs

• CAS Number: 138-65-8; 51-41-2(l); 51-41-2
• EC Number: 200-096-6
• MDL Number: MFCD00025592
• Beilstein Number: 2804840; 4231961
• Merck Index: 146695
• PubChem SID: 24891196; 46506201; 160963715
• PubChem CID: 439260
• CHEBI ID: 18357
• ATC CODE: C01CA03
• CHEMBL: 1437
• Chemspider ID: 388394
• DrugBank ID: DB00368
• KEGG ID: D00076
• Wikipedia Title: Norepinephrine

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.500885
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.0654356
• LogD (pH = 7.4): -1.8244592
• Log P: -0.6835134
• Molar Refractivity: 44.4557 cm^3
• Polarizability: 17.37873 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.4
• LOG S: -1.13
• Solubility (Water): 1.25e+01 g/l

PROPERTIES

Physical Property

• Solubility: 338 mg/mL [Predicted by ALOGPS]
• Apperance: off-white to tan crystalline
• Melting Point: ca 220°C dec.; L: 216.5–218 °C (decomp.); D/L: 191 °C (decomp.)
• Boiling Point: 442.6±40.0 °C (760 Torr)
• Density: 1.397±0.06 g/cm^3 (20 °C and 760 Torr)
• Vapor Pressure: 1.30e-8 Torr
• Optical Rotation: [α]20/D -45±3°, c = 5% in 1 M HCl; -45 (c=5 in 0.5N HCl)
• Hydrophobicity(logP): 0.2
• pKa: 9.57±0.10

Safety Information

• Storage Warning: Air & Light Sensitive; IRRITANT
• RTECS: DN5950000
• European Hazard Symbols: Highly toxic (T+); X
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 20/21/22; 26/27/28
• Safety Statements: 28-36/37-45; 9-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300; H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310; P264-P270-P301+P310-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Gene Information: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)rat ... Adra1a(29412), Adra1d(29413), Adra2a(25083), Adrb1(24925), Adrb2(24176), Drd1a(24316), Drd2(24318)

Product Information

• Purity: ≥98%; ≥98.0% (sum of enantiomers, HPLC); 95+%; 98%
• Empirical Formula (Hill Notation): C8H11NO3

DETAILS

DrugBank - DB00368

• Drug Groups: approved
• Description: Precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. [PubChem]
• Indication: Mainly used to treat patients in vasodilatory shock states such as septic shock and neurogenic shock and has shown a survival benefit over dopamine. Also used as a vasopressor medication for patients with critical hypotension.
• Pharmacology: Noradrenaline acts on both alpha-1 and alpha-2 adrenergic receptors to cause vasoconstriction. Its effect in-vitro is often limited to the increasing of blood pressure through antagonising alpha-1 and alpha-2 receptors and causing a resultant increase in systemic vascular resistance.
• Toxicity: In high dose and especially when it is combined with other vasopressors, it can lead to limb ischemia and limb death.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A7257

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Adrenergic neurotransmitter
Application
Norepinephrine is an adrenergic neurotransmitter used in the treatment of hypotension, depression, schizophrenia, and attention deficit/hyperactivity disorders.