DL-4-Chlorophenylalanine Chemical Properties

Melting point:

>240 °C (dec.)(lit.)

Boiling point:

339.5±32.0 °C(Predicted)

Density 

1.2409 (rough estimate)

refractive index 

1.5790 (estimate)

storage temp. 

room temp

solubility 

Aqueous Acid (Slightly), Methanol (Slightly)

pka

pK1: 2.08(+1);pK2: 8.96(0) (25°C)

form 

Powder

color 

White to almost white

Water Solubility 

slightly soluble

BRN 

2805758

CAS DataBase Reference

7424-00-2(CAS DataBase Reference)

EPA Substance Registry System

4-Chlorophenylalanine (7424-00-2)

Safety Information

Hazard Codes 

T

Risk Statements 

25-43

Safety Statements 

36/37-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

AY4390010

TSCA 

Yes

HS Code 

29224985

Hazardous Substances Data

7424-00-2(Hazardous Substances Data)

MSDS

• Language:English Provider:DL-4-Chlorophenylalanine
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

DL-4-Chlorophenylalanine Usage And Synthesis

Chemical Properties

Crystalline

Uses

An irreversible tryptophan hydroxylase inhibitor.

Uses

4-Chloro-DL-phenylalanine is an irreversible tryptophan hydroxylase inhibitor that depletes serotonin in the brain.

Uses

4-Chloro-DL-phenylalanine has been used:

• as tryptophan hydroxylase 1 (TPH1) inhibitor to treat kras⁺ male zebrafish
• to induce insomnia in rat models
• used to treat embryos to examine its effect on serotonin
• for the selection of Enterococcus faecalis transformants with pESentA32 plasmid
• to feed flies to explore serotonin effect

Definition

ChEBI: 2-amino-3-(4-chlorophenyl)propanoic acid is a phenylalanine derivative.

Biological Activity

4-Chloro-DL-phenylalanine (Fenclonine, PCPA, CP-10188) is a selective and irreversible inhibitor of tryptophan hydroxylase, a rate-limiting enzyme in the biosynthesis of serotonin (5-HYDROXYTRYPTAMINE). 4-Chloro-DL-phenylalanine acts pharmacologically to deplete endogenous levels of serotonin.

Biochem/physiol Actions

4-Chloro-DL-phenylalanine (PCPA) is an inhibitor of 5-hydroxytrytamine (5-HT) synthesis. It helps to improve the inflammation of lung tissue and remodeling pulmonary artery. PCPA can reduce the expression of tryptophan hydroxylase 1 (TPH1), matrix metalloproteinase (MMP) and pro-inflammatory factors.

Safety Profile

An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx and Cl-.

in vivo

4-Chloro-DL-phenylalanine(PCPA) markedly attenuates MCT(monocrotaline)-induced pulmonary vascular remodeling and lung inflammation, inhibits the expression of Tph-1 and SERT and suppresses the expression of MMP-2/-9, TIMP-1/-2, interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α) and intercellular adhesion molecule-1 (ICAM-1). PCPA inhibits 5-HT by suppressing Tph-1, regulating SERT and the serotonin downstream signaling pathway.

storage

Room temperature

DL-4-Chlorophenylalanine(7424-00-2)Related Product Information

• DL-O-CHLOROPHENYLALANINE
• DL-P-CHLOROPHENYLALANINE METHYL ESTER*HY,DL-4-CHLOROPHENYLALANINE METHYL ESTER HYDROCHLORIDE,DL-P-CHLOROPHENYLALANINE METHYL ESTER HYDROCHLORIDE
• DL-PENICILLAMINE
• 2-FLUORO-DL-PHENYLALANINE
• 4-Iodo-DL-phenylalanine
• 4-BROMO-DL-PHENYLALANINE
• 3-(3-Hydroxyphenyl)-DL-alanine
• DL-4-Cyanophenylalanine
• 2-AMINO-3-(3-METHOXY-PHENYL)-PROPIONIC ACID
• 2-Bromo-DL-Phenylalanine
• DL-3-(4-Fluorophenyl)alanine
• L-4-Chlorophenylalanine
• DL-4-CHLOROPHENYLALANINE ETHYL ESTER HYDROCHLORIDE,DL-P-CHLOROPHENYLALANINE ETHYL ESTER HYDROCHLORIDE
• BOC-DL-4-CHLOROPHENYLALANINE
• FMOC-DL-2-CHLOROPHENYLALANINE
• FMOC-DL-3-CHLOROPHENYLALANINE
• FMOC-DL-4-CHLOROPHENYLALANINE
• CBZ-DL-4-CHLOROPHENYLALANINE