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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

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

Target Organs

Respiratory system

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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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
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)
Shawn P Vorce et al.
Journal of analytical toxicology, 32(6), 444-450 (2008-07-26)
Designer piperazines, such as 1-benzylpiperazine (BZP) and 1-(3-trifluoromethylphenyl)-piperazine (TFMPP), are widely available and have become popular party drugs throughout the world. Used in many countries as legal alternatives to methamphetamine and ecstasy, these designer piperazines exhibit several of the same
A Paramá et al.
Diseases of aquatic organisms, 62(1-2), 97-102 (2005-01-15)
Philasterides dicentrarchi is a histiophagous ciliate that causes severe losses in turbot and sea bass farming. This study investigated the in vitro efficacy against P. dicentrarchi of 85 newly synthesized compounds and 12 commercial compounds, of which 2 are fluoroquinolones
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