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C3635

Sigma-Aldrich

4-Chloro-DL-phenylalanine methyl ester hydrochloride

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About This Item

Linear Formula:
ClC6H4CH2CH(NH2)CO2CH3·HCl
CAS Number:
14173-40-1
Molecular Weight:
250.12
EC Number:
238-024-0
MDL number:
MFCD00012530
UNSPSC Code:
12352209
PubChem Substance ID:
24278310
NACRES:
NA.32

form

powder

Quality Level

200

mp

186-189 °C (lit.)

storage temp.

−20°C

SMILES string

Cl.COC(=O)C(N)Cc1ccc(Cl)cc1

InChI

1S/C10H12ClNO2.ClH/c1-14-10(13)9(12)6-7-2-4-8(11)5-3-7;/h2-5,9H,6,12H2,1H3;1H

InChI key

GCBCWTWQAFLKJG-UHFFFAOYSA-N

Gene Information

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

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General description

4-Chloro-DL-phenylalanine methyl ester hydrochloride stimulates glucose intolerance in pregnant mice. Studies have shown that 4-Chloro-DL-phenylalanine methyl ester hydrochloride is associated with cognitive defects in rodents.

Application

4-Chloro-DL-phenylalanine methyl ester hydrochloride has been used to induce 5-hydroxytryptamine (5-HT) depletion in rats.

Biochem/physiol Actions

Tryptophan hydroxylase inhibitor. Crosses blood brain barrier better than p−chlorophenylalanine.

Storage Class Code

11 - Combustible Solids

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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Jessica E Monk et al.
Frontiers in behavioral neuroscience, 12, 246-246 (2018-11-09)
Negative affective states such as anxiety and depression pose a risk to animal welfare, however, practical tests for assessing these states in animals are limited. In humans, anxious individuals are shown to pay more attention toward threatening information than non-anxious
Vortioxetine dose-dependently reverses 5-HT depletion-induced deficits in spatial working and object recognition memory: a potential role for 5-HT1A receptor agonism and 5-HT3 receptor antagonism
du Jardin KG, et al.
European Neuropsychopharmacology, 24(1), 160-171 (2014)
Serotonin depletion results in a decrease of the neuronal activation caused by rivastigmine in the rat hippocampus
Kornum BR, et al.
Brain Research, 1073, 262-268 (2006)
Serotonin regulates pancreatic beta cell mass during pregnancy
Kim H, et al.
Nature Medicine, 16(7), 804-804 (2010)
K Linnet et al.
Brain research, 697(1-2), 251-253 (1995-10-30)
In order to study the impact of serotonin depletion on gene expression of the serotonin transporter (5-HTt) we measured 5-HTt mRNA levels by Northern blot in rats treated with p-chlorophenylalanine methyl ester (PCPA) for 10 days. Six rats received PCPA
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