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CAS 59119-18-5

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4-Hydroxy-1-(phenylmethyl)-4-piperidinecarboxylic acid

Description:
4-Hydroxy-1-(phenylmethyl)-4-piperidinecarboxylic acid, also known as baclofen, is a chemical compound characterized by its piperidine ring structure, which includes a hydroxyl group and a phenylmethyl substituent. This compound is a derivative of gamma-aminobutyric acid (GABA) and functions primarily as a muscle relaxant and antispastic agent. It exhibits properties that make it useful in the treatment of spasticity resulting from conditions such as multiple sclerosis and spinal cord injuries. The presence of the hydroxyl group contributes to its solubility in water, while the phenylmethyl group enhances its lipophilicity, allowing it to cross the blood-brain barrier effectively. Baclofen acts as a GABA_B receptor agonist, leading to inhibitory neurotransmission and muscle relaxation. Its pharmacokinetics include oral bioavailability and renal excretion, with a relatively short half-life. Side effects may include sedation, dizziness, and potential withdrawal symptoms upon abrupt discontinuation. Overall, baclofen is a significant compound in clinical settings for managing muscle spasticity.
Formula:C13H17NO3
InChI:InChI=1S/C13H17NO3/c15-12(16)13(17)6-8-14(9-7-13)10-11-4-2-1-3-5-11/h1-5,17H,6-10H2,(H,15,16)
InChI key:InChIKey=AFPNLFVPVQRYFL-UHFFFAOYSA-N
SMILES:C(N1CCC(C(O)=O)(O)CC1)C2=CC=CC=C2
Synonyms:
  • 4-Piperidinecarboxylic acid, 4-hydroxy-1-(phenylmethyl)-
  • 1-Benzyl-4-hydroxy-4-piperidinecarboxylic acid
  • 4-Hydroxy-1-(phenylmethyl)-4-piperidinecarboxylic acid
  • 1-Benzyl-4-hydroxypiperidine-4-carboxylic Acid
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