Baclofen

Base Information

• Chemical Name: Baclofen
• CAS No.: 1134-47-0
• Molecular Formula: C10H12ClNO2
• Molecular Weight: 213.664
• Hs Code.: 2922492050
• European Community (EC) Number: 214-486-9
• NSC Number: 755906,329137
• UN Number: 2811
• UNII: H789N3FKE8
• DSSTox Substance ID: DTXSID5022641
• Nikkaji Number: J3.661G
• Wikipedia: Baclofen
• Wikidata: Q413717
• NCI Thesaurus Code: C28858
• RXCUI: 1292
• Pharos Ligand ID: USJMSKZ6V3XF
• Metabolomics Workbench ID: 42589
• ChEMBL ID: CHEMBL701
• Mol file: 1134-47-0.mol

Synonyms:Apo Baclofen;Apo-Baclofen;ApoBaclofen;Atrofen;AWD, Baclofen;Ba-34,647;Ba-34647;Ba34,647;Ba34647;Baclofène Irex;Baclofène-Irex;BaclofèneIrex;Baclofen;Baclofen AWD;Baclophen;Baclospas;beta-(Aminomethyl)-4-chlorobenzenepropanoic Acid;beta-(p-Chlorophenyl)-gamma-aminobutyric Acid;Chlorophenyl GABA;CIBA-34,647-BA;CIBA34,647BA;Clofen;GABA, Chlorophenyl;Gen Baclofen;Gen-Baclofen;GenBaclofen;Genpharm;Lebic;Liorésal;Lioresal;Nu Baclo;Nu-Baclo;NuBaclo;PCP-GABA;PMS Baclofen;PMS-Baclofen;PMSBaclofen

Chemical Property of Baclofen

Chemical Property:

• Appearance/Colour: white to very faintly yellow solid
• Vapor Pressure: 6.01E-06mmHg at 25°C
• Melting Point: 208-210 ºC
• Refractive Index: 1.576
• Boiling Point: 364.3 ºC at 760 mmHg
• PKA: pKa 3.87±0.1(H2O) (Uncertain)
• Flash Point: 174.1 ºC
• PSA: 63.32000
• Density: 1.285 g/cm³
• LogP: 2.55730
• Storage Temp.: 2-8°C
• Solubility.: 1 M HCl: 50 mg/mL
• Water Solubility.: Soluble in dilute NaOH or dilute HCl. Soluble in water at approximately 4mg/ml at pH 7.6
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 213.0556563
• Heavy Atom Count: 14
• Complexity: 191
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Baclofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xn
• Hazard Codes: T,Xn
• Statements: 61-25-36/37/38-42/43-20/21/22
• Safety Statements: 53-22-36/37/39-45-52-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Autonomic Agents: Muscle Relaxants, Central
• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)O)CN)Cl
• Recent ClinicalTrials: Effect of Baclofen to Prevent Post-Traumatic Stress Disorder
• Recent EU Clinical Trials: International, multi-center, open-label FOLLOW-UP extension study assessing the long term safety and tolerability of PXT3003 in patients with Charcot-Marie-Tooth Disease type 1A.
• Recent NIPH Clinical Trials: Effects of baclofen on body weight in obese patients
• Indications: This product is an antispasmodic drug. It inhibits the transmission in spinal cord of mono-synapse multiple synapse. The mechanism is inhibiting the release of excitatory amino acid glutamate and aspartate through stimulating GABA receptor. Thus reduce the increased limbs muscle tension caused by spinal cord lesions, multiple sclerosis, and spinal cord injury. It can be used for treatment of muscle spasms caused by brain and spinal cord diseases or injuries.
• Uses: 1. The product is a relaxant and antispasmodic agent acting on the skeletal muscle of spinal cord. Suitable for treating multiple-sclerosis bones spasms, spinal infection, degenerated muscle spasms; spinal cord trauma, and neoplastic muscle spasms. 2. It is currently the most effective muscle relaxants with least side effects. Specific GABA-B receptor agonist. Muscle relaxant (skeletal) Baclofen may be used as a pharmaceutical secondary reference standard for the determination of the analyte in plasma samples by liquid chromatography tandem mass spectrometry and tablet formulations by UV spectroscopy, respectively. (±)-Baclofen has been used as γ-aminobutyric acid receptor B GABAB?receptor agonist: as well as control GABAergic drug to test its protective effects on 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)-induced dopaminergic toxicityto test its effects on in vivo motor function tests and performance of mutant miceto test its excitability effect on dopaminergic (DA) neurons of the ventral tegmental area (VTA) to test its effect in reducing dendritic excitability in Purkinje neurons
• Production method: Chlorobenzaldehyde and ethyl acetoacetate is condensed into chlorobenzene methylene-bis-ethyl acetoacetate. Add heating water for hydrolysis to obtain chlorophenyl glutaric acid. Dehydrate and cyclize to obtain chlorophenyl glutaric anhydride using acetic anhydride. Then perform amination reaction with concentrated aqueous ammonia to generate chlorophenyl glutaric acid imide. The open the ring, degrade to obtain the final product. Detailed procedures as follow: Add 42.25g β-(p-chlorophenyl) glutaric acid imide with stir to 200 mL aqueous solution containing 8.32g of sodium hydroxide. The mixture was heated at 50 °C for 10min, cool to 10-15 °C. Titrate for 200 mL aqueous solution of 40.9g of sodium hydroxide. After 20min, add 38.8g bromine, stir at 20-25 °C for 8h. Use concentrated hydrochloric acid to adjust the pH of the reaction solution to 7, and then precipitate out the fine crystals of i.e. [beta] (p-chlorophenyl) amino-gamma-acid. Re-crystallize in water with m.p. 206-208 °C.
• Therapeutic Function: Muscle relaxant
• Biological Functions: Baclofen (Lioresal) is the parachlorophenol analogue of the naturally occurring neurotransmitter γ-aminobutyric acid (GABA).
• Clinical Use: Baclofen is an agent of choice for treating spinal spasticity and spasticity associated with multiple sclerosis. It is not useful for treating spasticity of supraspinal origin. Doses should be increased gradually to a maximum of 100 to 150 mg per day, divided into four doses.
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: enhanced muscle relaxant effect with procainamide. Antidepressants: enhanced muscle relaxant effect with tricyclics. Antihypertensives: enhanced hypotensive effect. Lithium: use with caution.

Technology Process of Baclofen

There total 25 articles about Baclofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

3-(4-chlorophenyl)-4-(1,3-dioxoisoindolin-2-yl)-N-(quinolin-8-yl)butanamide → 4-amino-3-(4-chlorophenyl)butanoic acid (1134-47-0)

Guidance literature:

With hydrogenchloride; In water; at 130 ℃; for 24h; Sealed tube;

DOI:10.1021/jacs.7b06520

Reference yield: 87.0%

3-(4-chlorophenyl)-4-((((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)carbonyl)amino)butanoic acid → 4-amino-3-(4-chlorophenyl)butanoic acid (1134-47-0)

Guidance literature:

With sodium L-ascorbate; fluorescein free acid; In aq. phosphate buffer; for 0.5h; pH=7.4; Irradiation;

DOI:10.1002/anie.201811261

Reference yield: 81.0%

4-(4-chlorophenyl)pyrrolidin-2-one (22518-27-0) → 4-amino-3-(4-chlorophenyl)butanoic acid (1134-47-0)

Guidance literature:

With hydrogenchloride; water; In water; for 16h; Reflux;

DOI:10.1039/c3ra42201a

upstream raw materials:

4-(4-chlorophenyl)pyrrolidin-2-one

ethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-chlorophenyl)butanoate

ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate

(E)-3-(4-chlorophenyl)but-2-enoic acid

Downstream raw materials:

3-(4-chlorophenyl)-4-pyrrol-1-ylbutyric acid

n-chlorooctane

4-Amino-3-(4-chloro-phenyl)-butyric acid octyl ester; hydrochloride

Refernces

• 1、 Maniukiewicz, Waldemar,Oracz, Monika,Sieroń, Les?aw. "Structural characterization and Hirshfeld surface analysis of racemic baclofen". . p. 271 - 275. Retrieved 2016.
• 2、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF BACLOFEN AND ITS INTERMEDIATE". Page/Page column 17. . Retrieved 2017/02/09.
• 3、 -. "A balufen green industrial production method (by machine translation)". . . Retrieved 2017/05/02.