4-Amino-3-phenylbutanoic acid

Base Information

• Chemical Name: 4-Amino-3-phenylbutanoic acid
• CAS No.: 1078-21-3
• Deprecated CAS: 35568-37-7
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• European Community (EC) Number: 214-079-6
• UNII: T2M58D6LA8
• DSSTox Substance ID: DTXSID70870838
• Nikkaji Number: J12.174F
• Wikipedia: Phenibut
• Wikidata: Q419559
• Pharos Ligand ID: 9VW474H912TD
• Metabolomics Workbench ID: 154261
• ChEMBL ID: CHEMBL315818
• Mol file: 1078-21-3.mol

Synonyms:4-amino-3-phenylbutyric acid;4-amino-3-phenylbutyric acid hydrochloride;4-amino-3-phenylbutyric acid, (DL)-(+-)-mixture;4-amino-3-phenylbutyric acid, (L)-(-)-isomer;beta-(aminomethyl)benzenepropanoic acid;beta-(aminomethyl)hydrocinnamic acid;beta-phenyl-gamma-aminobutyric acid;citrocard;fenibut;fenibut citrate;noophen;phenibut;phenybut;phenyl-GABA

Chemical Property of 4-Amino-3-phenylbutanoic acid

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 7.98E-05mmHg at 25°C
• Melting Point: 194.0-202 °C
• Refractive Index: 1.5710 (estimate)
• Boiling Point: 327.8 °C at 760 mmHg
• PKA: 4.10±0.10(Predicted)
• Flash Point: 152.1 °C
• PSA: 63.32000
• Density: 1.161 g/cm³
• LogP: 2.70590
• Solubility.: Free base: 35 mg/mL in DMSO (195.29 mM) at 25 °C (SellekChem, 2019).Hydrochloride salt (Cayman, 2016): 25 mg/ml in DMF; 20 mg/ml in DMSO; 14 mg/ml in ethanol; 10 mg/mL in PBS (pH 7.2).
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

4-Amino-3-phenylbutanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)O)CN
• Description: Phenibut, also known as fenibut, phenigamma, and beta-phenyl-gamma-aminobutyric acid, is a derivative of the neurotransmitter GABA. It was developed in Russia,and there it has been used clinically since the 1960s to treat anxiety and related conditions，including insomnia(Lapin，2001). Phenibut has anxiolytic properties and is commonlycompared to benzodiazepines and baclofen.Structurally，phenibut issimilar to GABA, with the addition of the phenyl ring. This allows thecompound to more easily cross the blood-brain barrier, but also changesits activity profile (Shulgina,1986). Scientific studies demonstrate that phenibut can be safely used to treat anxiety, depression,epilepsy, speech disorders, and insomnia.
• Uses: 4-amino-3-phenylbutanoic acid (cas# 1078-21-3) is a GABAA receptor agonist, used for treatment of disorders influenced by dysfunction of pancreatic β cells and also used in combination with other agents.

Technology Process of 4-Amino-3-phenylbutanoic acid

There total 49 articles about 4-Amino-3-phenylbutanoic acid 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: 100.0%

C24H25NO2 → (R)-Phenibut (1078-21-3,35568-36-6,62596-63-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; for 14h;

Reference yield: 98.0%

4-nitro-3-phenyl butanoic acid (41441-41-2) → 4-amino-3-phenylbutanoic acid (1078-21-3,35568-36-6,62596-63-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 60 ℃; under 45004.5 Torr;

DOI:10.1002/anie.201409765

Reference yield: 95.0%

4-(1,3-dioxoisoindolin-2-yl)-3-phenyl-N-(quinolin-8-yl)butanamide → 4-amino-3-phenylbutanoic acid (1078-21-3,35568-36-6,62596-63-8)

Guidance literature:

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

DOI:10.1021/jacs.7b06520

upstream raw materials:

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine

4-phenylpyrrolidin-2-one

3-cyano-3-phenyl propionic acid

hydrogenchloride

Downstream raw materials:

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

(R)-Phenibut

(S)-Phenibut

(3R)-4-nitro-3-phenylbutanal

Refernces

• 1、 Li, Xiuxiu,You, Cai,Yang, Yusheng,Yang, Yuhong,Li, Pan,Gu, Guoxian,Chung, Lung Wa,Lv, Hui,Zhang, Xumu. "Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position". . p. 1919 - 1924. Retrieved 2018.
• 2、 Liu, Zhen,Wang, Yanyan,Wang, Zichen,Zeng, Tian,Liu, Peng,Engle, Keary M.. "Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation". supporting information. p. 11261 - 11270. Retrieved 2017/08/22.