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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14ClNO
Molecular Weight 211.6883
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4-(4-CHLOROPHENYL)-4-PIPERIDINOL

SMILES

c1cc(ccc1C2(CCNCC2)O)Cl

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

Molecular Formula C11H14ClNO
Molecular Weight 211.6883
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9090.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
In vitro characterization of the metabolism of haloperidol using recombinant cytochrome p450 enzymes and human liver microsomes.
2001 Dec
Liquid chromatographic-mass spectrometric determination of haloperidol and its metabolites in human plasma and urine.
2002 Aug 25
Synthesis and pharmacological activity of 4-(4'-(chlorophenyl)-4-hydroxypiperidine) derivatives.
2005 Jan
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.
2005 Jul-Aug
Physical stability of the amorphous state of loperamide and two fragment molecules in solid dispersions with the polymers PVP-K30 and PVP-VA64.
2005 Jun
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 Dec
Simultaneous analysis of haloperidol, its three metabolites and two other butyrophenone-type neuroleptics by high performance liquid chromatography with dual ultraviolet detection.
2006 Feb
Identification of a new functional target of haloperidol metabolite: implications for a receptor-independent role of 3-(4-fluorobenzoyl) propionic acid.
2006 Oct
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 Sep
[Chemical toxicological analysis of haloperidol metabolite 4-(4-chlorophenyl)-4-hydroxypipiridine in urine by high-performance liquid chromatography].
2009 Jan-Feb
Bis[4-(4-chloro-phen-yl)-4-hydroxy-piperidinium] dipicrate dimethyl sulfoxide solvate.
2010 Apr 30
4-(4-Chloro-phen-yl)piperidin-4-ol.
2010 Feb 6
4-(4-Chloro-phen-yl)-4-hy-droxy-piperidinium maleate maleic acid solvate.
2010 Jul 14
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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).
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:28:30 UTC 2021
Edited
by admin
on Sat Jun 26 08:28:30 UTC 2021
Record UNII
UND92FKS0W
Record Status Validated (UNII)
Record Version
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Name Type Language
4-(4-CHLOROPHENYL)-4-PIPERIDINOL
Systematic Name English
NSC-89568
Code English
LOPERAMIDE HYDROCHLORIDE IMPURITY C [EP]
Common Name English
CPHP
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
FDA UNII
UND92FKS0W
Created by admin on Sat Jun 26 08:28:30 UTC 2021 , Edited by admin on Sat Jun 26 08:28:30 UTC 2021
PRIMARY
EPA CompTox
39512-49-7
Created by admin on Sat Jun 26 08:28:30 UTC 2021 , Edited by admin on Sat Jun 26 08:28:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
254-479-8
Created by admin on Sat Jun 26 08:28:30 UTC 2021 , Edited by admin on Sat Jun 26 08:28:30 UTC 2021
PRIMARY
PUBCHEM
38282
Created by admin on Sat Jun 26 08:28:30 UTC 2021 , Edited by admin on Sat Jun 26 08:28:30 UTC 2021
PRIMARY
CAS
39512-49-7
Created by admin on Sat Jun 26 08:28:30 UTC 2021 , Edited by admin on Sat Jun 26 08:28:30 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE INACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP