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Merck
CN

C8655

4-Chloro-L-phenylalanine

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
Beilstein:
2416150
EC Number:
238-023-5
MDL number:
MFCD00063065
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24893091
NACRES:
NA.32

Key Documents

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Product Name

4-Chloro-L-phenylalanine,

form

powder

Quality Level

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)

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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 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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0125
BCCH5598
BCCC7109
BCBW7232
BCBW2200

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Mechanism of metal-independent hydroxylation by Chromobacterium violaceum phenylalanine hydroxylase
Carr RT, et al.
Biochemistry, 34(22), 7525-7532 (1995)
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
Serotonin synthesis and metabolism-related molecules in a human prostate cancer cell line
Shinka T, et al.
Oncology Letters, 2(2), 211-215 (2011)
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
Karolina Pytka et al.
Frontiers in pharmacology, 9, 1146-1146 (2018-11-10)
Numerous studies have proven that both stimulation and blockade of 5-HT1A and the blockade of 5-HT7 receptors might cause the anxiolytic-like effects. Biased agonists selectively activate specific signaling pathways. Therefore, they might offer novel treatment strategies. In this study, we
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。

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