U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H21NO.ClH
Molecular Weight 255.784
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRECLAMOL HYDROCHLORIDE, (R)-

SMILES

Cl.CCCN1CCC[C@@H](C1)C2=CC(O)=CC=C2

InChI

InChIKey=NRHUDETYKUBQJT-ZOWNYOTGSA-N
InChI=1S/C14H21NO.ClH/c1-2-8-15-9-4-6-13(11-15)12-5-3-7-14(16)10-12;/h3,5,7,10,13,16H,2,4,6,8-9,11H2,1H3;1H/t13-;/m0./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H21NO
Molecular Weight 219.3226
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(+)-3-(3-Hydroxyphenyl)-N-(1-propyl)piperidine ((+)-3-PPP or preclamor, (R)) is an agonist of the sigma receptors and also acts as a dopamine receptor agonist with autoreceptor as well as postsynaptic receptor stimulatory properties. In vivo experiments have shown, that preclamor, (R) inhibited DOPA accumulation in the striatum, nucleus accumbens, and medial prefrontal cortex.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Target ID: Q5BJF2
Gene ID: 27346.0
Gene Symbol: TMEM97
Target Organism: Homo sapiens (Human)
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Target ID: Q5BJF2
Gene ID: 27346.0
Gene Symbol: TMEM97
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Involvement of direct inhibition of NMDA receptors in the effects of sigma-receptor ligands on glutamate neurotoxicity in vitro.
2000-09-15
Rat liver and kidney contain high densities of sigma 1 and sigma 2 receptors: characterization by ligand binding and photoaffinity labeling.
1994-06-15
Pharmacological characteristics of hyperambulation induced by the sigma ligand (+)-3-PPP in rats.
1994-05
Differential agonist profile of the enantiomers of 3-PPP at striatal dopamine autoreceptors: dependence on extracellular dopamine.
1991-07

Sample Use Guides

in rats: at doses above 3 mg/kg (s.c.) increased the ambulatory activity of rats
Route of Administration: Other
In Vitro Use Guide
In vitro, both (+) (preclamol, R)- and (-)-3-PPP reduced basal DOPA accumulation with a similar order of potency (apparent EC50 = 2.1 and 1.0 microns, respectively) and maximal effect, although they were less potent than the D2 DA receptor agonist quinpirole (EC50 = 0.15 microM).
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:08:16 GMT 2025
Edited
by admin
on Mon Mar 31 22:08:16 GMT 2025
Record UNII
S695806J1A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRECLAMOL HYDROCHLORIDE, (R)-
Preferred Name English
Code System Code Type Description
EPA CompTox
DTXSID1045796
Created by admin on Mon Mar 31 22:08:16 GMT 2025 , Edited by admin on Mon Mar 31 22:08:16 GMT 2025
PRIMARY
PUBCHEM
202477
Created by admin on Mon Mar 31 22:08:16 GMT 2025 , Edited by admin on Mon Mar 31 22:08:16 GMT 2025
PRIMARY
CAS
89874-80-6
Created by admin on Mon Mar 31 22:08:16 GMT 2025 , Edited by admin on Mon Mar 31 22:08:16 GMT 2025
PRIMARY
FDA UNII
S695806J1A
Created by admin on Mon Mar 31 22:08:16 GMT 2025 , Edited by admin on Mon Mar 31 22:08:16 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE