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C8655

4-Chloro-L-phenylalanine

Name: 4-Chloro-<SC>L</SC>-phenylalanine
Brand: SIGMA

Tryptophan hydroxylase inhibitor, powder

Synonym(s):

L-PCPA

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About This Item

Linear Formula:

ClC₆H₄CH₂CH(NH₂)CO₂H

CAS Number:

14173-39-8

Molecular Weight:

199.63

NACRES:

NA.32

PubChem Substance ID:

24893091

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

238-023-5

MDL number:

MFCD00063065

Beilstein/REAXYS Number:

2416150

Form:

powder

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Properties

Product Name

4-Chloro-L-phenylalanine,

form

powder

Quality Segment

200

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.

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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