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C6506

Sigma-Aldrich

4-Chloro-DL-phenylalanine

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Synonym(s):
PCP, PCPA
Linear Formula:
ClC6H4CH2CH(NH2)CO2H
CAS Number:
7424-00-2
Molecular Weight:
199.63
EC Number:
231-051-9
MDL number:
MFCD00002601
UNSPSC Code:
12352209
PubChem Substance ID:
24278081
NACRES:
NA.32

form

solid

Quality Level

100

greener alternative product score

old score: 2
new score: 1
Find out more about DOZN™ Scoring

greener alternative product characteristics

Less Hazardous Chemical Syntheses
Designing Safer Chemicals
Design for Energy Efficiency
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

>240 °C (dec.) (lit.)

greener alternative category

, Re-engineered

storage temp.

room temp

SMILES string

NC(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)

InChI key

NIGWMJHCCYYCSF-UHFFFAOYSA-N

Gene Information

human ... TPH1(7166) , TPH2(121278)

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General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles "Less Hazardous Chemical Syntheses", "Designing Safer Chemicals" and "Design for Energy Efficiency". Click here to view its DOZN scorecard.

Application

4-Chloro-DL-phenylalanine has been used:
  • as tryptophan hydroxylase 1 (TPH1) inhibitor to treat kras+ male zebrafish
  • to induce insomnia in rat models
  • used to treat embryos to examine its effect on serotonin
  • for the selection of Enterococcus faecalis transformants with pESentA32 plasmid
  • to feed flies to explore serotonin effect

Biochem/physiol Actions

4-Chloro-DL-phenylalanine (PCPA) is an inhibitor of 5-hydroxytrytamine (5-HT) synthesis. It helps to improve the inflammation of lung tissue and remodeling pulmonary artery. PCPA can reduce the expression of tryptophan hydroxylase 1 (TPH1), matrix metalloproteinase (MMP) and pro-inflammatory factors.
Tryptophan hydroxylase inhibitor.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H317

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Frederic D L Leusch et al.
Chemosphere, 191, 868-875 (2017-11-07)
Environmental chemicals can induce thyroid disruption through a number of mechanisms including altered thyroid hormone biosynthesis and transport, as well as activation and inhibition of the thyroid receptor. In the current study six in vitro bioassays indicative of different mechanisms of
PCPA protects against monocrotaline-induced pulmonary arterial remodeling in rats: potential roles of connective tissue growth factor
Bai Y, et al.
Testing, 8(67), 111642-111642 (2017)
Hadas Tsivion-Visbord et al.
Translational psychiatry, 10(1), 305-305 (2020-09-03)
Schizophrenia is a debilitating psychiatric disorder with a significant number of patients not adequately responding to treatment. Phencyclidine (PCP) is used as a validated model for schizophrenia, shown to reliably induce positive, negative and cognitive-like behaviors in rodents. It was
Mustafa Alshawaqfeh et al.
Biology direct, 12(1), 4-4 (2017-02-02)
Recent developments of high throughput sequencing technologies allow the characterization of the microbial communities inhabiting our world. Various metagenomic studies have suggested using microbial taxa as potential biomarkers for certain diseases. In practice, the number of available samples varies from
Mariana G Fronza et al.
PloS one, 12(11), e0187445-e0187445 (2017-11-02)
A series of phenylselanyl-1H-1,2,3-triazole-4-carbonitriles with different substituents were screened for their binding affinity with serotonin transporter (SERT) and dopamine transporter (DAT) by docking molecular. 5-(4methoxyphenyl)-1-(2-(phenylselanyl)phenyl)-1H-1,2,3-triazole-4-carbonitrile (SeTACN) exhibited the best conformation with SERT even higher than fluoxetine and serotonin, suggesting a
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Chromatograms

application for HPLC

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