4-(4-CHLOROPHENYL)-4-PIPERIDINOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H14ClNO
Molecular Weight	211.688
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 4-(4-CHLOROPHENYL)-4-PIPERIDINOL

Structure Search

SMILES

OC1(CCNCC1)C2=CC=C(Cl)C=C2

InChI

InChIKey=LZAYOZUFUAMFLD-UHFFFAOYSA-N

InChI=1S/C11H14ClNO/c12-10-3-1-9(2-4-10)11(14)5-7-13-8-6-11/h1-4,13-14H,5-8H2

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1599504
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24827597 | http://www.hmdb.ca/metabolites/HMDB60902

4-(4-Chlorophenyl)-4-piperidinol (CPPO) is one of haloperidol metabolite. Neurotoxicity studies in frogs, which have been used to detect N-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) action, showed that CPPO did not mimic the neurotoxicity of MPTP but caused a delayed and persistent freezing action in Rana pipiens frogs. It is proposed that this action may contribute to some of the delayed side-effects associated with haloperidol therapy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D2 receptor 311 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24827597	Antagonist 2849		9090.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.	2010-07-14	21588324
Bis[4-(4-chloro-phen-yl)-4-hydroxy-piperidinium] dipicrate dimethyl sulfoxide solvate.	2010-04-30	21579241
4-(4-Chloro-phen-yl)piperidin-4-ol.	2010-02-06	21580330
[Chemical toxicological analysis of haloperidol metabolite 4-(4-chlorophenyl)-4-hydroxypipiridine in urine by high-performance liquid chromatography].	2009-04-18	19371012
Sensitive determination of 4-(4-bromophenyl)-4-hydroxypiperidine, a metabolite of bromperidol, in rat plasma by HPLC with fluorescence detection after pre-column derivatization using 4-fluoro-7-nitro-2,1,3-benzoxadiazole.	2006-12	17142985
Identification of a new functional target of haloperidol metabolite: implications for a receptor-independent role of 3-(4-fluorobenzoyl) propionic acid.	2006-10	17029599
Sensitive determination of 4-(4-chlorophenyl)-4-hydroxypiperidine, a metabolite of haloperidol, in a rat biological sample by HPLC with fluorescence detection after pre-column derivatization using 4-fluoro-7-nitro-2,1,3-benzoxadiazole.	2006-09	16506267
Simultaneous analysis of haloperidol, its three metabolites and two other butyrophenone-type neuroleptics by high performance liquid chromatography with dual ultraviolet detection.	2006-02	16034821
Physical stability of the amorphous state of loperamide and two fragment molecules in solid dispersions with the polymers PVP-K30 and PVP-VA64.	2005-06	15911228
Synthesis and pharmacological activity of 4-(4'-(chlorophenyl)-4-hydroxypiperidine) derivatives.	2005-01	15635232
Salt formation in solid dispersions consisting of polyacrylic acid as a carrier and three basic model compounds resulting in very high glass transition temperatures and constant dissolution properties upon storage.	2004-10-18	15894472
Liquid chromatographic-mass spectrometric determination of haloperidol and its metabolites in human plasma and urine.	2002-08-25	12127331
Comparison of SSI with APCI as an interface of HPLC-mass spectrometry for analysis of a drug and its metabolites.	2002-03	11908800
In vitro characterization of the metabolism of haloperidol using recombinant cytochrome p450 enzymes and human liver microsomes.	2001-12	11717183

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Cell membranes (D2L-FlpIn CHO, 3 μg) were incubated with varying concentrations of test compound 7 (4-(4-Chlorophenyl)-4-piperidinol) in binding buffer (20 mM HEPES, 100 mM NaCl, 6 mM MgCl2, 1 mM EGTA, and 1 mM EDTA, pH 7.4) containing 0.05 nM of [3H]spiperone and 100 μM GppNHp to a final volume of 1 mL and were incubated at 37 °C for 3 h. Binding was terminated by fast-flow filtration over GF/B membranes using a Brandel harvester followed by three washes with ice-cold 0.9% NaCl. Bound radioactivity was measured in a Tri-Carb 2900TR liquid scintillation counter (PerkinElmer).

Name

Type

Language

NSC-89568

Preferred Name

English

4-(4-CHLOROPHENYL)-4-PIPERIDINOL

Systematic Name

English

CPHP

Common Name

English

LOPERAMIDE HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

O4-PIPERIDINOL, 4-(4-CHLOROPHENYL)-

Systematic Name

English

4-(4-CHLOROPHENYL)PIPERIDIN-4-OL

Systematic Name

English

Code System Code Type Description

NSC

89568