(3R)-4-amino-3-(4-chlorophenyl)butanoic acid hydrochloride

• ChemBase ID: 134379
• Molecular Formular: C10H13Cl2NO2
• Molecular Mass: 250.12172
• Monoisotopic Mass: 249.03233402
• SMILES: c1cc(ccc1[C@@H](CC(=O)O)CN)Cl.Cl
• Canonical SMILES: NC[C@@H](c1ccc(cc1)Cl)CC(=O)O.Cl
• InChI: InChI=1S/C10H12ClNO2.ClH/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14;/h1-4,8H,5-6,12H2,(H,13,14);1H/t8-;/m0./s1
• InChIKey: WMNUVYYLMCMHLU-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-4-amino-3-(4-chlorophenyl)butanoic acid hydrochloride
• IUPAC Traditional name: (3R)-4-amino-3-(4-chlorophenyl)butanoic acid hydrochloride
• Synonyms: Arbaclofen hydrochloride; R(+)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid hydrochloride; STX209; R(+)-Baclofen hydrochloride

Database IDs

• CAS Number: 63701-55-3
• MDL Number: MFCD00078579
• PubChem SID: 162228655; 24895006
• PubChem CID: 44601

CALCULATED PROPERTIES

• Acid pKa: 3.8868947
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.79014736
• LogD (pH = 7.4): -0.7832327
• Log P: -0.78240025
• Molar Refractivity: 54.8292 cm^3
• Polarizability: 21.613943 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; H2O: soluble26 mg/mL (Solutions may be stored for several weeks at 4 °C.)
• Apperance: white solid
• Optical Rotation: [α]28/D +3.8°, c = 0.9 in methanol(lit.)

Safety Information

• RTECS: MW5084350
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GABBR1(2550)mouse ... GABBR1(54393)rat ... GABBR1(81657)

DETAILS

Sigma Aldrich - G013

Biochem/physiol Actions
R(+)-Baclofen is a GABAB receptor agonist; more active enantiomer; skeletal muscle relaxant.
Other Notes
Same enantiomer as R(-)-baclofen free base.