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C8655

Sigma-Aldrich

4-Chlor-L-Phenylalanin

Synonym(e):

L-PCPA

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About This Item

Lineare Formel:
ClC6H4CH2CH(NH2)CO2H
CAS-Nummer:
14173-39-8
Molekulargewicht:
199.63
Beilstein:
2416150
EG-Nummer:
238-023-5
MDL-Nummer:
MFCD00063065
UNSPSC-Code:
12352209
eCl@ss:
32160406
PubChem Substanz-ID:
24893091
NACRES:
NA.32

Form

powder

mp (Schmelzpunkt)

263 °C (dec.) (lit.)

Lagertemp.

−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

InChIKey

NIGWMJHCCYYCSF-QMMMGPOBSA-N

Angaben zum Gen

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

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Anwendung

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. Wirkung

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.

Verpackung

Bottomless glass bottle. Contents are inside inserted fused cone.

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Preisangaben

H9772

5-Hydroxy-L-Tryptophan, powder

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Die Dokumentenbibliothek aufrufen

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
Behavioural and electrographic effects of L-5-hydroxytryptophan and D, L-parachlorophenyl-alanine on epileptic Senegalese baboon (Papio papio)
Wada JA, et al.
Electroencephalography and Clinical Neurophysiology, 33(5), 520-526 (1972)
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
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
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