Skip to Content
Merck
CN

C8655

4-Chloro-L-phenylalanine

Tryptophan hydroxylase inhibitor, powder

Synonym(s):

L-PCPA

Sign In to View Organizational & Contract Pricing.

Select a Size

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
Quality level:
200

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCH0125
BCCH5598
BCCC7109
BCBW7232
BCBW2200

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
Yang Bai et al.
International journal of molecular medicine, 33(2), 373-382 (2013-12-18)
The present study was performed to investigate the effects of 4-chloro-DL-phenylalanine (PCPA), a tryptophan hydroxylase (Tph) inhibitor (TphI), on pulmonary vascular remodeling and lung inflammation in monocrotaline (MCT)-induced pulmonary arterial hypertension (PAH) in rats. Animal models of PAH were established
View All Related Papers

Articles

Serotonin Synthesis & Metabolism

Serotonin is stored in cells and metabolized by MAO, influencing CNS, GI, and platelet functions.

血清素合成及代谢

血清素（5-羟色胺）主要存在于三种主要细胞类型中：i）中杻神经系统（CNS）和肠肌间神经丛中的血清素能神经元，ii）胃肠道粘膜中的肠嗜铬细胞，和iii）血小板。血清素的代谢主要通过外部线粒体膜酶单胺氧化酶（MAO）进行，它以两种分子亚型存在，分别称为MAO-A和MAO-B。

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service