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Sigma-Aldrich

1-(3-Chlorophenyl)piperazine hydrochloride

99%

Synonym(s):

m-CPP

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About This Item

Empirical Formula (Hill Notation):
C10H13ClN2 · xHCl
CAS Number:
65369-76-8
Molecular Weight:
196.68 (free base basis)
EC Number:
265-718-0
MDL number:
MFCD00039032
UNSPSC Code:
12352100
PubChem Substance ID:
24847652
NACRES:
NA.22

assay

99%

form

powder

mp

210-214 °C (dec.) (lit.)

solubility

methanol: soluble

SMILES string

Cl.Clc1cccc(c1)N2CCNCC2

InChI

1S/C10H13ClN2.ClH/c11-9-2-1-3-10(8-9)13-6-4-12-5-7-13;/h1-3,8,12H,4-7H2;1H

InChI key

MHXPYWFZULXYHT-UHFFFAOYSA-N

Gene Information

rat ... Htr1a(24473)

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General description

1-(3-Chlorophenyl)piperazine hydrochloride is sold as Ecstasy mimic tablets and is the major metabolite of the antidepressant medications trazodone and nefazodone.

Application

1-(3-Chlorophenyl)piperazine hydrochloride (CPP) has been used in determination of designer piperazines in urine specimens using GC-MS and LC-ESI-MS. CPP has been used to investigate the in vitro efficacy of newly synthesized compounds such as fluoroquinolones (norfloxacine and lomefloxacine) against Philasterides dicentrarchi .

Biochem/physiol Actions

1-(3-Chlorophenyl)piperazine induces hypophagia in food-deprived and freely feeding rats. CPP has affinity for 11 neurotransmitter receptor binding sites in human brain membranes.
5-HT2c serotonin receptor agonist; metabolite of trazodone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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Horst Schicknick et al.
Cerebral cortex (New York, N.Y. : 1991), 18(11), 2646-2658 (2008-03-07)
Previous studies in the auditory cortex of Mongolian gerbils on discrimination learning of the direction of frequency-modulated tones (FMs) revealed that long-term memory formation involves activation of the dopaminergic system, activity of the protein kinase mammalian target of rapamycin (mTOR)
A Hamik et al.
Biological psychiatry, 25(5), 569-575 (1989-03-01)
The affinity of 1-(m-chlorophenyl)piperazine (mCPP) for 11 neurotransmitter receptor binding sites was determined in human brain membranes. mCPP is essentially equipotent at all 5-hydroxytryptamine (5-HT) receptor subtypes (IC50 values ranging from 360 to 1300 nM). The drug displays similar affinity
G A Kennett et al.
British journal of pharmacology, 103(4), 2016-2020 (1991-08-01)
1. 1-3(Chlorophenyl)piperazine (mCPP) (5 mg kg-1, i.p.) inhibited 2 h food intake in rats previously deprived of food for one day. Ten 5-hydroxytryptamine (5-HT) antagonists given s.c. opposed this hypophagic response. Calculated ID50 values correlated significantly with reported affinities (r
Nan Zhang et al.
Journal of ethnopharmacology, 219, 23-30 (2018-03-17)
Cananga odorata essential oil, known as ylang-ylang essential oil (YYO), was commonly used in the aromatherapy for relaxation and mood adjusting use. In our previous study, YYO played anxiolytic effects on the mice in several behavioral tests that based on
Xiao Chen et al.
Behavioral and brain functions : BBF, 17(1), 4-4 (2021-05-20)
Obsessive-compulsive disorder (OCD) is a mental disease with heterogeneous behavioral phenotypes, including repetitive behaviors, anxiety, and impairments in cognitive functions. The brain regions related to the behavioral heterogeneity, however, are unknown. We systematically examined the behavioral phenotypes of three OCD
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