(2R,3R)-2,3-dihydroxybutanedioic acid 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol hydrate

• ChemBase ID: 73263
• Molecular Formular: C12H19NO10
• Molecular Mass: 337.27996
• Monoisotopic Mass: 337.10089581
• SMILES: c1(c(ccc(c1)[C@H](CN)O)O)O.OC(=O)[C@@H]([C@H](C(=O)O)O)O.O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.NC[C@@H](c1ccc(c(c1)O)O)O.O
• InChI: InChI=1S/C8H11NO3.C4H6O6.H2O/c9-4-8(12)5-1-2-6(10)7(11)3-5;5-1(3(7)8)2(6)4(9)10;/h1-3,8,10-12H,4,9H2;1-2,5-6H,(H,7,8)(H,9,10);1H2/t8-;1-,2-;/m01./s1
• InChIKey: LNBCGLZYLJMGKP-LUDZCAPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid 4-[(1R)-2-amino-1-hydroxyethyl]benzene-1,2-diol hydrate
• IUPAC Traditional name: L-tartaric acid norepinephrine hydrate; L(+)-tartaric acid norepinephrine hydrate
• Synonyms: Levophed; Noradrenaline bitartrate monohydrate; L-Arterenol hydrogen L-tartrate; L-Noradrenaline hydrogen L-tartrate monohydrate; L-Norepinephrine bitartrate salt; L-Norepinephrine hydrogen L-tartrate monohydrate; 4-[(1R)-2-Amino-1-hydroxyethyl]-1,2-benzenediol Hydrogen Tartrate Monohydrate; L-Noradrenaline Bitartrate Monohydrate; Levoarterenol Bitartrate Monohydrate; L-Arterenol Bitartrate Monohydrate; L-Norepinephrine Hydrogen L-Tartrate Monohydrate; L-(-)-Norepinephrine (+)-bitartrate salt monohydrate; L-(-)-降肾上腺素 (+)-酒石酸氢盐 一水合物; L-(-)-去甲肾上腺素 (+)-酒石酸氢盐 一水合物

Database IDs

• CAS Number: 108341-18-0
• MDL Number: MFCD00150449
• Beilstein Number: 4078502
• PubChem SID: 24897627; 162038183; 24897754; 24886487; 24277787
• PubChem CID: 3047796

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: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble46 mg/mL; H2O: soluble50 mg/mL, clear; Methanol; Water
• Apperance: white solid; White Solid
• Melting Point: 102-105 °C; 128-130°C
• Optical Rotation: [α]20/D -11.5±1°, c = 2% in H2O

Safety Information

• Storage Condition: -20°C; Refrigerator
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; 3
• Risk Statements: 26/27/28
• Safety Statements: 22-26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P264-P280-P284-P302 + P350-P310
• 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; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2; UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%; ≥99.0% (sum of enantiomers, HPLC)
• Grade: analytical standard
• Packaging: vial of 200 mg
• Suitability: meets USP testing specifications
• Empirical Formula (Hill Notation): C8H11NO3 · C4H6O6 · H2O

DETAILS

Selleck Chemicals - S2615

Research Area: Endocrinology
Biological Activity:
Noradrenaline bitartrate monohydrate (Levophed) is a direct alpha-adrenergic receptors stimulator.Noradrenaline bitartrate monohydrate (Levophed) also directly stimulates the beta-adrenergic receptors of the heart (beta1-adrenergic receptors), but not those of the bronchi (beta2-adrenergic receptors). Noradrenaline functions as a peripheral vasoconstrictor (alpha-adrenergic action) and as an inotropic stimulator of the heart and dilator of coronary arteries (beta-adrenergic action). These actions result in an increase in the force of myocardial contraction, increase in peripheral resistance and a rise in diastolic and systolic pressures. [1][2]References on Noradrenaline bitartrate monohydrate (Levophed)[1] http://en.wikipedia.org/wiki/Norepinephrine, , [2] Proc Natl Acad Sci U S A., 2010 Mar 30, 107(13):6058-63

Sigma Aldrich - A9512

Biochem/physiol Actions
Adrenergic neurotransmitter, vasoconstrictor.
Caution
Light sensitive

Sigma Aldrich - 74500

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.

Sigma Aldrich - N3146

包装
Supplied in amber screw-cap vials

Toronto Research Chemicals - N674505

Demethylated precursor of epinephrine (adrenaline). It is a sympathomimetic hormone produced by the adrenal gland.

REFERENCES

• Heneka MT et al. Proc Natl Acad Sci U S A. 2010 Mar 30;107(13):6058-63.
• Kesby, J., et al.: Neurosci. Lett., 461, 155 (2009)
• Anderson, J., et al.: Brain Res., 1281 1 (2009)
• Mao, Y., et al.: Eur. J. Pharmacol., 615, 61 (2009)