133933-81-0

Basic information

• Product Name: (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID
• Synonyms: (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID;4-amino-3-(5-chloro-2-thienyl)butyric acid;β-(5-Chloro-2-thienyl)GABA
• CAS NO: 133933-81-0
• Molecular Formula: C₈H₁₀ClNO₂S
• Molecular Weight: 219.69
• Mol File: 133933-81-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 360.9°Cat760mmHg
• Flash Point: 172.1°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 7.71E-06mmHg at 25°C
• Refractive Index: 1.602
• CAS DataBase Reference: (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID(133933-81-0)
• EPA Substance Registry System: (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID(133933-81-0)

Safety Data

• Hazardous Substances Data: 133933-81-0(Hazardous Substances Data)

Usage

General Description

(+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is a chemical compound with the molecular formula C8H10ClNO2S. It is an amino acid derivative containing a thienyl ring and a chlorine atom. (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is commonly used in pharmaceutical and medicinal research, particularly in the development of antipsychotic and anticonvulsant drugs. It has been found to exhibit activity on the central nervous system and may have potential therapeutic applications in the treatment of various neurological disorders. Additionally, it may also possess antimicrobial and anti-inflammatory properties. Further research and studies are needed to fully understand the potential benefits and applications of (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID.

InChI:InChI=1/C8H10ClNO2S/c9-7-2-1-6(13-7)5(4-10)3-8(11)12/h1-2,5H,3-4,10H2,(H,11,12)

Synthetic route

ethyl 3-(5-chloro-2-thienyl)-4-nitrobutanoate (133933-51-4) → 4-amino-3-(5-chlorothien-2-yl)butanoic acid (133933-81-0)

Conditions	Yield
With sodium hydroxide; hydrogen; nickel 1.) EtOH, 1 atm, RT, 2.) aq. EtOH, reflux, 1 h; Yield given. Multistep reaction;

5-Chloro-2-thiophenecarboxaldehyde (7283-96-7) → 4-amino-3-(5-chlorothien-2-yl)butanoic acid (133933-81-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / benzene / 7 h / Heating 2: 64 percent / Triton B / 18 h / 85 °C 3: 1.) H2, 2.) 10 N NaOH / 1.) Raney Ni / 1.) EtOH, 1 atm, RT, 2.) aq. EtOH, reflux, 1 h View Scheme

ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate (133933-42-3) → 4-amino-3-(5-chlorothien-2-yl)butanoic acid (133933-81-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / Triton B / 18 h / 85 °C 2: 1.) H2, 2.) 10 N NaOH / 1.) Raney Ni / 1.) EtOH, 1 atm, RT, 2.) aq. EtOH, reflux, 1 h View Scheme

Upstream product

• 133933-42-3 ethyl 3-(5-chloro-2-thienyl)-prop-2-enoate 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 133933-51-4 ethyl 3-(5-chloro-2-thienyl)-4-nitrobutanoate 

Relevant articles and documents

METHODS OF TREATING FRAGILE X SYNDROME, DOWN?S SYNDROME, AUTISM AND RELATED DISORDERS

Disclosed herein are methods of treating fragile X syndrome, fragile X-associated tremor/ataxia syndrome, Down?s syndrome and other forms of mental retardation, and/or autism comprising administering a GABA B agonist prodlug to a subject suffering therefrom. The GABAB agonist prodrugs can be compounds of Formula (I), (II) or (III) as disclosed herein

Use of GABAB receptor agonists as reflux inhibitors

PCT No. PCT/SE97/01555 Sec. 371 Date Nov. 12, 1997 Sec. 102(e) Date Nov. 12, 1997 PCT Filed Sep. 15, 1997 PCT Pub. No. WO98/11885 PCT Pub. Date Mar. 26, 1998The present invention relates to the use of GABAB receptor agonists for the inhibition of transient lower esophageal sphincter relaxations, and for the treatment of gastro-esophageal reflux disease.