(3R)-3-(aminomethyl)-5-methylhexanoic acid

• ChemBase ID: 176887
• Molecular Formular: C8H17NO2
• Molecular Mass: 159.22608
• Monoisotopic Mass: 159.12592879
• SMILES: C(C[C@H](CC(=O)O)CN)(C)C
• Canonical SMILES: NC[C@@H](CC(=O)O)CC(C)C
• InChI: InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m1/s1
• InChIKey: AYXYPKUFHZROOJ-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(aminomethyl)-5-methylhexanoic acid
• IUPAC Traditional name: (3R)-3-(aminomethyl)-5-methylhexanoic acid
• Synonyms: (3R)-3-(Aminomethyl)-5-methylhexanoic acid; (R)-3-(Aminomethyl)-5-methylhexanoic acid; PD 144550; ent-Pregabalin; (R)-Pregabalin

Database IDs

• CAS Number: 148553-51-9
• PubChem SID: 164232797
• PubChem CID: 125889

CALCULATED PROPERTIES

• Acid pKa: 4.8009205
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.4076396
• LogD (pH = 7.4): -1.3444575
• Log P: -1.3455846
• Molar Refractivity: 43.68 cm^3
• Polarizability: 17.506392 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 162-167°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P704785

R-Enantiomer of Pregabalin. A GABA analogue used as an anticonvulsant. Anxiolytic analgesic used to treat peripheral neuropathic pain and fibromyalgia (less potent than the S-Enantiomer).

REFERENCES

• Field, M.J. et al.: Br. J. Pharmacol., 132, 1 (2001)
• Taylor, C.P., at al.: Epilepsy Res., 14, 11 (2001)