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C8655

Sigma-Aldrich

4-Chloro-L-phenylalanine

Synonyme(s) :

L-PCPA

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About This Item

Formule linéaire :
ClC6H4CH2CH(NH2)CO2H
Numéro CAS:
14173-39-8
Poids moléculaire :
199.63
Numéro Beilstein :
2416150
Numéro CE :
238-023-5
Numéro MDL:
MFCD00063065
Code UNSPSC :
12352209
eCl@ss :
32160406
ID de substance PubChem :
24893091
Nomenclature NACRES :
NA.32

Forme

powder

Pf

263 °C (dec.) (lit.)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

NIGWMJHCCYYCSF-QMMMGPOBSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

H9772

5-Hydroxy-L-tryptophan, powder

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
Mechanism of metal-independent hydroxylation by Chromobacterium violaceum phenylalanine hydroxylase
Carr RT, et al.
Biochemistry, 34(22), 7525-7532 (1995)
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
James Oluwagbamigbe Fajemiroye et al.
Iranian journal of pharmaceutical research : IJPR, 17(2), 613-626 (2018-06-09)
The search for psychoactive plants possessing therapeutic potential in the treatment of anxiety and depression has attracted growing interest. One such plant, Nymphaea lotus (commonly known as water lily), is used in traditional medicine for analgesic and sedative effects. The
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