4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

• ChemBase ID: 73260
• Molecular Formular: C9H13NO3
• Molecular Mass: 183.20442
• Monoisotopic Mass: 183.08954328
• SMILES: c1(c(ccc(c1)C(CNC)O)O)O
• Canonical SMILES: CNCC(c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3
• InChIKey: UCTWMZQNUQWSLP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• IUPAC Traditional name: (+-)-adrenaline; DL-adrenaline
• Synonyms: (±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; (±)-Adrenalin; 3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; DL-Adrenaline; (+/-)-3,4-Dihydroxy-α-[(methylamino)methyl]benzyl Alcohol; 1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol; Epirenamine; Racepinefrine; Racepinephrine; rac Epinephrine; DL-Adrenaline; 3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol; (±)-3,4-Dihydroxy-α-(methylaminomethyl)benzyl alcohol; DL-EPINEPHRINE; (±)-Epinephrine; 4-(1-Hydroxy-2-(MethylaMino)ethyl)benzene-1,2-diol; (±)-3,4-二羟基-α-(甲基氨基)苯甲醇; 3,4-二羟基-α-甲胺甲基苄醇; 4-[1-羟基-2-(甲基氨基)乙基]-1,2-苯二酚; 消旋肾上腺素; (±)-肾上腺素

Database IDs

• CAS Number: 329-65-7
• EC Number: 206-347-6
• MDL Number: MFCD00063027
• PubChem SID: 162038180; 24894424
• PubChem CID: 838

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: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Acid; DMSO (hot)
• Apperance: Brown Solid
• Melting Point: 196-199°C; 197 °C (dec.)(lit.); 205-210°C (dec.)

Safety Information

• Storage Condition: -20°C; 2-8°C, Store Under Nitrogen, Protect from light; Refrigerator
• RTECS: DO2975000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 24-36/37/38; R:25
• Safety Statements: 26-36/37-45; S:28-36/37/39-45-53
• 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: H311-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P312
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: GPCR
• Gene Information: rat ... Adra1a(29412), Adra2a(25083), Adrb1(24925), Adrb2(24176)

Product Information

• Purity: ≥95%; 95%; 98%
• Salt Data: Free Base
• Linear Formula: (HO)2C6H3CH(CH2NHCH3)OH

DETAILS

MP Biomedicals - 02151064

Crystalline

Selleck Chemicals - S2523

Biological Activity:
DL-Adrenaline is a hormone and a neurotransmitter secreted by the medulla of the adrenal glands. In medicine DL-Adrenaline is used chiefly as a stimulant in cardiac arrest, as a vasoconstrictor in shock, and as a bronchodilator and antispasmodic in bronchial asthma. DL-Adrenaline is found in small amounts in the body and is essential for maintaining cardiovascular homeostasis because of its ability to divert blood to tissues under stress. DL-Adrenaline acts by binding to a variety of adrenergic receptors. DL-Adrenaline is a nonselective agonist of all adrenergic receptors, including α1, α2, β1, β2, and β3 receptors. Epinephrine’s binding to these receptors triggers a number of metabolic changes. Binding to α-adrenergic receptors inhibits insulin secretion by the pancreas, stimulates glycogenolysis in the liver and muscle, and stimulates glycolysis in muscle. [1][2]References on DL-Adrenaline[1] http://en.wikipedia.org/wiki/Epinephrine, , [2] Am J Physiol. , 1982 Apr, 242(4):H593-601

Sigma Aldrich - E1635

Biochem/physiol Actions
肾上腺受体激动剂

Sigma Aldrich - 316741

Biochem/physiol Actions
Adrenoceptor agonist.

Toronto Research Chemicals - E588585

Endogenous catcholamine with combined α-and β-agonist activity. Principal sympathomimetic hormone produced by the adrenal medulla. Bronchodilator; cardiostimulant; mydriatic; antiglaucoma.

REFERENCES

• Berecek KH et al. Am J Physiol. 1982 Apr;242(4):H593-601.
• Cucinotta, V., et al.: J. Pharm. Biomed. Anal., 37, 1009 (2005)
• Marin-Zamora, M., et al.: J. Agric. Food Chem., 55, 4569 (2005)
• Kao, B., et al.: J. Perinatol., 28, 205 (2005)