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

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

Uses

Used in Pharmaceutical Research:
(+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is used as a research compound for the development of antipsychotic and anticonvulsant drugs. Its activity on the central nervous system makes it a promising candidate for the treatment of neurological disorders.
Used in Medicinal Development:
In the medicinal industry, (+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is utilized as a key component in the formulation of drugs targeting neurological conditions. Its potential therapeutic effects are currently under investigation to determine its efficacy and safety.
Used in Antimicrobial Applications:
(+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is being studied for its antimicrobial properties, which could be beneficial in the development of new antibiotics to combat resistant bacteria.
Used in Anti-inflammatory Research:
(+/-)-4-AMINO-3-(5-CHLORO-2-THIENYL)-BUTANOIC ACID is also being explored for its potential anti-inflammatory effects, which could lead to the creation of new treatments for inflammatory conditions.
Note: The specific application types and reasons are inferred from the provided materials, as the exact uses were not detailed. The applications listed are based on the general properties and potential of the compound as described.

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

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

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 GABA and GABAB agonists

The present invention provides methods of stimulating tissue growth, including islet cell growth, by administering GABA or a GABA agonist to act on GABAB receptors and GABAB-like receptors to activate cell replication.

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.

3-thienyl- and 3-furylaminobutyric acids. Synthesis and binding GABA(B) receptor studies

Baclofen (β-(p-chlorophenyl)-GABA) is a selective agonist for the bicuculline-insensitive GABA(B) receptor. The search for new compounds that bind to the GABA(B) receptor is very important to clarify structural requirements. We report herein the synthesis and the binding studies of variously substituted 3-thienyl- and 3-furylaminobutyric acids. 4-Amino-3-(5-methyl-2-thienyl)butyric acid (5d) and 4-amino-3-(5-chloro-2-thienyl)butyric acid (5h) are potent and specific ligands for GABA(B) receptor. The IC50 values for the displacement of (R)-(-)-[3H]baclofen are 1.34 and 0.61 μM for 5d and 5h, respectively, as compared to 0.33 μM for baclofen.