4-Chloro-DL-phenylalanine - CAS 7424-00-2
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
4-Chloro-DL-phenylalanine
Catalog Number:
7424-00-2
Synonyms:
DL-4-Chlorophenylalanine;p-Chlorophenylalanine;(S)-2-amino-3-(4-chlorophenyl)propanoic acid;2-Amino-3-(4-chlorophenyl)propanoic acid;DL-3-(4-Chlorophenyl)alanine;Fenclonin;Fenclonine;PCP;PCPA;CP-10188
CAS Number:
7424-00-2
Description:
4-Chloro-DL-phenylalanine is a pharmaceutical intermediate. It acts as a selective and irreversible inhibitor of tryptophan hydroxylase. It is a rate-limiting enzyme in the biosynthesis of serotonin. It has been used experimentally to treat carcinoid syndrome. It is used in scientific research in humans and animals to investigate the effects of serotonin depletion. It binds irreversibly to tryptophan hydroxylase to cause depletion of serotonin in the brain.
Molecular Weight:
199.63
Molecular Formula:
C9H10ClNO2
Quantity:
Grams to Kilograms
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1=CC(=CC=C1CC(C(=O)O)N)Cl
InChI:
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)
InChIKey:
NIGWMJHCCYYCSF-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 7424-00-2 4-Chloro-DL-phenylalanine

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Reference Reading


1.4-Chloro-DL-phenylalanine protects against monocrotaline‑induced pulmonary vascular remodeling and lung inflammation.
Bai Y1, Wang HM1, Liu M1, Wang Y1, Lian GC1, Zhang XH1, Kang J2, Wang HL1. Int J Mol Med. 2014 Feb;33(2):373-82. doi: 10.3892/ijmm.2013.1591. Epub 2013 Dec 16.
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 using Sprague-Dawley (SD) rats by a single intraperitoneal injection of MCT (60 mg/kg). PCPA (50 or 100 mg/kg/day) was administered to the rats with PAH. On day 22, hemodynamic measurements and morphological observations of the lung tissues were performed. The levels of Tph-1 and serotonin transporter (SERT) in the lungs were analyzed by immunohistochemistry and western blot analysis. The expression of matrix metalloproteinase (MMP)-2 and MMP-9, tissue inhibitor of metalloproteinase (TIMP)-1 and TIMP-2 and inflammatory cytokines were assayed by western blot analysis. The activity of MMP-2 and MMP-9 was evaluated by gelatin zymography (GZ).
2.Molecular structure, vibrational spectra, NBO, UV and first order hyperpolarizability, analysis of 4-Chloro-dl-phenylalanine by density functional theory.
Govindarasu K1, Kavitha E2. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Dec 10;133:799-810. doi: 10.1016/j.saa.2014.06.019. Epub 2014 Jun 13.
The Fourier transform infrared (4000-400cm(-1)) and Fourier transform Raman (3500-50cm(-1)) spectra of 4-Chloro-dl-phenylalanine (4CLPA) were recorded and analyzed. The equilibrium geometry, bonding features and harmonic vibrational wavenumbers were investigated with the help of density functional theory (DFT) method using B3LYP/6-31G(d,p) as basis set. The observed vibrational wavenumbers were compared with the calculated results. Natural bond orbital analysis confirms the presence of intramolecular charge transfer and the hydrogen bonding interaction. Predicted electronic absorption spectra from TD-DFT calculation have been analyzed comparing with the UV-Vis (200-800nm) spectrum. The effects of chlorine and ethylene group substituent in benzene ring in the vibrational wavenumbers have been analyzed. The HOMO-LUMO energy gap explains the charge interaction taking place within the molecule. The first order hyperpolarizability (β0) and related properties (β, α0 and Δα) of 4CLPA were calculated.