PCPA methyl ester hydrochloride

Names

[ Name ]:
PCPA methyl ester hydrochloride

[Synonym ]:
4-Chloro-DL-Phe-OMe HCl
3-(4-Chlorophenyl)-1-methoxy-1-oxo-2-propanaminium chloride
Benzeneethanaminium, 4-chloro-α-(methoxycarbonyl)-, chloride (1:1)
MFCD00012530
methyl 2-amino-3-(4-chlorophenyl)propanoate,hydrochloride
DL-4-Chlorophenylalanine methyl ester hydrochloride
UNII:OC0YKX1H41
Methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride
DL-p-Chlorophenylalanine methyl ester hydrochloride
EINECS 238-024-0
H-DL-Phe(4-Cl)-OMe.HCl

Biological Activity

[Description]:

PCPA methyl ester hydrochloride (4-Chloro-DL-phenylalanine methyl ester hydrochloride), a reversible tryptophan hydroxylase inhibitor, is a serotonin (5-HT) synthesis inhibitor. PCPA methyl ester hydrochloride crosses the blood brain barrier and reduces 5-HT central availability[1][2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Tryptophan Hydroxylase

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[Target]

serotonin

Tryptophan Hydroxylase

[In Vivo]

PCPA methyl ester hydrochloride (250-500 mg/kg; oral administration; daily; for 8 weeks) treatment significantly decreases serotonin levels in both hippocampus and cortex[3]. In C57BL/6 elite male mice, 5-HT levels decreased by 85% and 55% in the hippocampus of mice treated with oral or ip PCPA methyl ester hydrochloride, respectively, whereas in the prefrontal cortex, 5-HT levels decreased by 65% (oral) and 50% (ip)[3]. Animal Model: C57BL/6 elite male mice (3 months old)[3] Dosage: 500 mg/kg per day for the first 2 days and 250 mg/kg for the rest of the treatment Administration: Oral administration; daily; for 8 weeks Result: Serotonin levels were significantly decreased in both hippocampus and cortex.

[References]

[1]. Dool-Ri Oh, et al. Sedative and hypnotic effects of Vaccinium bracteatum Thunb. through the regulation of serotonegic and GABA A-ergic systems: Involvement of 5-HT 1A receptor agonistic activity. Biomed Pharmacother. 2019 Jan;109:2218-2227.

[2]. Fabio Bellia, et al. Transient serotonin depletion at adolescence, but not at early infancy, reduced subsequent anxiety-like behavior and alcohol intake in female mice. Psychopharmacology (Berl). 2021 Jan;238(1):215-225.

[3]. ocío B Foltran, et al. Neurochemical, Behavioral, and Neurogenic Validation of a Hyposerotonergic Animal Model by Voluntary Oral Consumption of para-Chlorophenylalanine. ACS Chem Neurosci. 2020 Mar 18;11(6):952-959.

Chemical & Physical Properties

[ Boiling Point ]:
296.3ºC at 760 mmHg

[ Melting Point ]:
186-189 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₃Cl₂NO₂

[ Molecular Weight ]:
250.122

[ Flash Point ]:
133ºC

[ Exact Mass ]:
249.032333

[ PSA ]:
52.32000

[ LogP ]:
2.88510

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AY4452100

CHEMICAL NAME :: Alanine, 3-(p-chlorophenyl)-, methyl ester, hydrochloride, DL-

CAS REGISTRY NUMBER :: 14173-40-1

LAST UPDATED :: 198910

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C10-H12-Cl-N-O2.Cl-H

MOLECULAR WEIGHT :: 250.14

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 400 mg/kg

SEX/DURATION :: male 4 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - mating performance (e.g. # sperm positive females per # females mated; # copulations per # estrus cycles)

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 166,1433,1969

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AY4452100

[ HS Code ]:
2922499990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2922499990

[ Summary ]:
HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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