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

Product Name

4-Chloro-L-phenylalanine,

InChI key

NIGWMJHCCYYCSF-QMMMGPOBSA-N

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

SMILES string

N[C@@H](Cc1ccc(Cl)cc1)C(O)=O

form

powder

mp

263 °C (dec.) (lit.)

storage temp.

−20°C

Quality Level

200

Gene Information

human ... TPH1(7166), TPH2(121278)
mouse ... TPH1(21990), TPH2(216343)
rat ... TPH1(24848), TPH2(317675)

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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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In-Frame and Unmarked Gene Deletions in Burkholderia cenocepacia via an Allelic Exchange System Compatible with Gateway Technology.

Mustafa Fazli et al.

Applied and environmental microbiology, 81(11), 3623-3630 (2015-03-22)

Burkholderia cenocepacia is an emerging opportunistic pathogen causing life-threatening infections in immunocompromised individuals and in patients with cystic fibrosis, which are often difficult, if not impossible, to treat. Understanding the genetic basis of virulence in this emerging pathogen is important

Serotonin synthesis and metabolism-related molecules in a human prostate cancer cell line

Shinka T, et al.

Oncology Letters, 2(2), 211-215 (2011)

Dietary protein source and butyrylated high-amylose maize starch included in a high-protein diet determines the urinary metabolome of rats.

Zahra Sattari Najafabadi et al.

International journal of food sciences and nutrition, 70(3), 255-266 (2018-08-31)

Intake of red and processed meat increases the risk of colorectal cancer (CRC), whereas dairy product consumption and the intake of dietary fibre are negatively associated with this risk. We investigated the effect of (i) low-protein diets with either whey

Mechanism of metal-independent hydroxylation by Chromobacterium violaceum phenylalanine hydroxylase

Carr RT, et al.

Biochemistry, 34(22), 7525-7532 (1995)

Expression and functional activity of neurotransmitter system components in sea urchins? early development

Nikishin DA, et al.

Zygote, 24(2), 206-218 (2016)

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