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HomeProduct name listDL-4-Chlorophenylalanine

DL-4-Chlorophenylalanine

Synonym(s):PCP;PCPA

  • CAS NO.:7424-00-2
  • Empirical Formula: C9H10ClNO2
  • Molecular Weight: 199.63
  • MDL number: MFCD00002601
  • EINECS: 231-051-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-09 19:38:33
DL-4-Chlorophenylalanine Structural

What is DL-4-Chlorophenylalanine?

Chemical properties

Crystalline

The Uses of DL-4-Chlorophenylalanine

An irreversible tryptophan hydroxylase inhibitor.

The Uses of DL-4-Chlorophenylalanine

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

The Uses of DL-4-Chlorophenylalanine

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

What are the applications of Application

4-Chloro-DL-phenylalanine is an irreversible tryptophan hydroxylase inhibitor

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

Properties of DL-4-Chlorophenylalanine

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 for DL-4-Chlorophenylalanine

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
GHS Hazard Statements H301:Acute toxicity,oral
H317:Sensitisation, Skin
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for DL-4-Chlorophenylalanine

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