4-[(1R)-1-hydroxy-2-[(2H3)methylamino]ethyl]benzene-1,2-diol

• ChemBase ID: 168086
• Molecular Formular: C9H13NO3
• Molecular Mass: 183.20442
• Monoisotopic Mass: 183.08954328
• SMILES: c1(c(ccc(c1)[C@H](CNC)O)O)O
• Canonical SMILES: CNC[C@@H](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/t9-/m0/s1
• InChIKey: UCTWMZQNUQWSLP-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-1-hydroxy-2-[(^2H₃)methylamino]ethyl]benzene-1,2-diol
• IUPAC Traditional name: 4-[(1R)-1-hydroxy-2-[(^2H₃)methylamino]ethyl]benzene-1,2-diol
• Synonyms: 4-[(1R)-1-Hydroxy-2-(methylamino-d3)ethyl]-1,2-benzenediol; (R)-Epinephrine-d3; Renoform-d3; Renostypticin-d3; Adnephrine-d3; Adrenal-d3; Adrenalin-d3; Adrenaline-d3; l-Epinephrine-d3; Levoepinephrine-d3; L-(-)-Epinephrine-d3

Database IDs

• PubChem SID: 162262218
• PubChem CID: 49849560

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 HCl; DMSO
• Apperance: Off-White to Pale Purple Solid
• Melting Point: 193-195°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E588583

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

REFERENCES

• Malmejac, et al.: Physiol. Rev., 44, 186 (1964)
• Pohorecky, L.A., et al.: Pharmacol. Rev., 23, (1964)
• Hebert, P., et al.: J. Emerg. Med., 9, 487 (1964)
• McLean-Tooke, et al.: Br. Med. J., 327, 1332 (1964)