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C8655

4-Chloro-L-phenylalanine

Tryptophan hydroxylase inhibitor, powder

Synonym(s):

L-PCPA

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$391.00

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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

Key Documents

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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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1 of 4

This Item
P0878C5438C3912
4-Chloro-L-phenylalanine

Sigma-Aldrich

C8655

4-Chloro-L-phenylalanine

O-Phospho-L-serine

Sigma-Aldrich

P0878

O-Phospho-L-serine

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt ≥95% (HPLC), powder

Sigma-Aldrich

C5438

8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt ≥97.0% (HPLC), powder

Sigma-Aldrich

C3912

8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt

form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

-

storage temp.

−20°C

storage temp.

−20°C

mp

263 °C (dec.) (lit.)

mp

190 °C (lit.)

mp

-

mp

-

Gene Information

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

Gene Information

human ... GRM4(2914), GRM7(2917), GRM8(2918)

Gene Information

-

Gene Information

human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)

Application

4-Chloro-L-phenylalanine (L-PCPA) has been used:
  • to block serotonin synthesis by inhibiting tryptophan hydroxylase (TPH)[1]
  • to study its behavioral and electrographic effects on epileptic senegalese baboon (Papio papio)[2]
  • as a substrate for Chromobacterium violaceum phenylalanine hydroxylase[3]
  • to incubate sea urchin embryos for immunohistochemistry[4]

Biochem/physiol Actions

4-Chloro-L-phenylalanine (L-PCPA) inhibits the synthesis of 5-hydroxytryptamine (5-HT).[5] 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.[6]
Tryptophan hydroxylase inhibitor.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

related product

Product No.
Description
Pricing

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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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
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

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