C8655

4-Chloro-L-phenylalanine

• Synonym(s): L-PCPA
• Linear Formula: ClC₆H₄CH₂CH(NH₂)CO₂H
• CAS Number: 14173-39-8
• Molecular Weight: 199.63
• Beilstein: 2416150
• EC Number: 238-023-5
• MDL number: MFCD00063065
• UNSPSC Code: 12352209
• eCl@ss: 32160406
• PubChem Substance ID: 24893091
• NACRES: NA.32

Properties

• form: powder
• mp: 263 °C (dec.) (lit.)
• storage temp.: −20°C
• SMILES string: N[C@@H](Cc1ccc(Cl)cc1)C(O)=O
• InChI: 1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1
• InChI key: NIGWMJHCCYYCSF-QMMMGPOBSA-N
• Gene Information: human ... TPH1(7166) , TPH2(121278) ; mouse ... TPH1(21990) , TPH2(216343) ; rat ... TPH1(24848) , TPH2(317675)

Description

Application

4-Chloro-L-phenylalanine (L-PCPA) has been used:

• to block serotonin synthesis by inhibiting tryptophan hydroxylase (TPH)
• to study its behavioral and electrographic effects on epileptic senegalese baboon (Papio papio)
• as a substrate for Chromobacterium violaceum phenylalanine hydroxylase
• to incubate sea urchin embryos for immunohistochemistry

Biochem/physiol Actions

4-Chloro-L-phenylalanine (L-PCPA) inhibits the synthesis of 5-hydroxytryptamine (5-HT). 4-Chloro-DL-phenylalanine (PCPA) depletes the serotonin levels in the brain by its inhibitory effect on tryptophan hydroxylase (Tph). Studies support the protective effects of PCPA against monocrotaline-induced pulmonary vascular remodeling as well as in lung inflammation.

Tryptophan hydroxylase inhibitor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Safety Information

• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves