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

• ChemBase ID: 155870
• Molecular Formular: C8H12ClNO3
• Molecular Mass: 205.63878
• Monoisotopic Mass: 205.05057093
• SMILES: c1cc(c(cc1[C@H](CN)O)O)O.Cl
• Canonical SMILES: NC[C@@H](c1ccc(c(c1)O)O)O.Cl
• InChI: InChI=1S/C8H11NO3.ClH/c9-4-8(12)5-1-2-6(10)7(11)3-5;/h1-3,8,10-12H,4,9H2;1H/t8-;/m0./s1
• InChIKey: FQTFHMSZCSUVEU-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol hydrochloride
• IUPAC Traditional name: norepinephrine hydrochloride
• Synonyms: L-Arterenol hydrochloride; L-Noradrenaline hydrochloride; L-Norepinephrine hydrochloride

Database IDs

• CAS Number: 329-56-6
• EC Number: 206-345-5
• MDL Number: MFCD00064560
• Beilstein Number: 3916100
• PubChem SID: 24886484; 162250008
• PubChem CID: 11672905

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Melting Point: ~150 °C (dec.)
• Optical Rotation: [α]20/D -38.5±5°, c = 2% in H2O

Safety Information

• RTECS: DN6475000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C8H11NO3 · HCl

DETAILS

Sigma Aldrich - 74480

Biochem/physiol Actions
Adrenal medullary stress hormone, mediator of the fight-or-flight response; and the primary neurotransmitter in the post-ganglionic sympathetic (adrenergic) nervous system.