(2R,3R)-2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• ChemBase ID: 73061
• Molecular Formular: C13H19NO9
• Molecular Mass: 333.29126
• Monoisotopic Mass: 333.10598119
• SMILES: c1(c(ccc(c1)[C@@H](O)CNC)O)O.C(=O)([C@H](O)[C@@H](O)C(=O)O)O
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.CNC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1
• InChIKey: YLXIPWWIOISBDD-NDAAPVSOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC Traditional name: L-tartaric acid; epinephrine; L(+)-tartaric acid; epinephrine
• Synonyms: L-Adrenaline D-hydrogentartrate; (-)-Epinephrine (+)-bitartrate salt; L-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol D-hydrogen bitartrate salt; L-Adrenaline (+)-bitartrate salt; L-Epinephrine D-hydrogentartrate; Adrenalini tartras; D02149; Adrenalinetartrate; Epinephrine bitartrate; L-Adrenalin Bitartrate; Adrenaline Acid Tartrate; Lyophrin; L-(-)-EPINEPHRINE-(+)-BITARTRATE; 酒石酸肾上腺素; 副肾素 (+)-酒石酸氢盐; L-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol D-hydrogen 酒石酸氢盐; (-)-肾上腺素 (+)-酒石酸氢盐

Database IDs

• CAS Number: 51-42-3
• EC Number: 200-097-1
• MDL Number: MFCD00035077
• PubChem SID: 24850718; 162037981; 24277774; 24894379
• PubChem CID: 5815

CALCULATED PROPERTIES

• Acid pKa: 9.69426
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.8488538
• LogD (pH = 7.4): -1.6309718
• Log P: -0.42952928
• Molar Refractivity: 49.2303 cm^3
• Polarizability: 19.213377 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; H2O: soluble
• Apperance: white solid
• Melting Point: ~155 °C (dec.); 147-154
• Optical Rotation: [α]20/D -17±1°, c = 1% in H2O

Safety Information

• Storage Condition: -20°C; 2-8°C, Store Under Nitrogen, Protect from light
• RTECS: DO3500000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; I
• Australian Hazchem: 2XE
• Risk Statements: 28-36/37/38; R:28
• Safety Statements: 26-28-36/37-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H315-H319-H335
• GHS Precautionary statements: P261-P264-P301 + P310-P305 + P351 + P338
• 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 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: adrenergicreceptor
• Gene Information: human ... ADRA1A(148), ADRA1B(147), ADRA1D(146), ADRA2A(150), ADRA2B(151), ADRA2C(152), ADRB1(153), ADRB2(154), ADRB3(155)

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC)
• Grade: analytical standard; Ph Eur
• Salt Data: Bitartrate
• Packaging: vial of 200 mg
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C9H13NO3 · C4H6O6

DETAILS

MP Biomedicals - 02195166

Crystalline

Selleck Chemicals - S2521

Biological Activity:
Epinephrine bitartrate (D02149, Adrenalinium) is alpha- and beta-adrenergic receptor stimulator. Epinephrine bitartrate (D02149, Adrenalinium) can cause relaxation of cardiac and bronchial smooth muscle and dilation of skeletal muscles. Epinephrine bitartrate (D02149, Adrenalinium) also decreases aqueous humor production. Epinephrine bitartrate (D02149, Adrenalinium) increases aqueous outflow. Epinephrine bitartrate (D02149, Adrenalinium) dilates pupils by contracting dilator muscle. Epinephrine bitartrate (D02149, Adrenalinium) is a bitartrate salt of epinephrine which is a hormone and a neurotransmitter. Epinephrine increases heart rate, constricts blood vessels, dilates air passages and participates in the fight-or-flight response of the sympathetic nervous system. [1][2]

Sigma Aldrich - E1016

Biochem/physiol Actions
肾上腺素能受体激动剂。
包装
Supplied in amber screw-cap vials

Sigma Aldrich - 17809

Biochem/physiol Actions
Adrenergic receptor agonist.

Sigma Aldrich - E4375

Biochem/physiol Actions
肾上腺素能受体激动剂。
Caution
Light sensitive

Sigma Aldrich - 02260

Biochem/physiol Actions
Adrenergic receptor agonist.

REFERENCES

• Berecek KH et al. Am J Physiol. 1982 Apr;242(4)