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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H21NO
Molecular Weight 219.3226
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=HTSNFXAICLXZMA-ZDUSSCGKSA-N
InChI=1S/C14H21NO/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/t13-/m0/s1

HIDE SMILES / InChI

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
Differential agonist profile of the enantiomers of 3-PPP at striatal dopamine autoreceptors: dependence on extracellular dopamine.
1991 Jul
Pharmacological characteristics of hyperambulation induced by the sigma ligand (+)-3-PPP in rats.
1994 May
Involvement of direct inhibition of NMDA receptors in the effects of sigma-receptor ligands on glutamate neurotoxicity in vitro.
2000 Sep 15

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 Sat Dec 16 08:06:56 GMT 2023
Edited
by admin
on Sat Dec 16 08:06:56 GMT 2023
Record UNII
8L7H229K4I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRECLAMOL, (R)-
Common Name English
(R)-(+)-3-PPP
Common Name English
(+)-3-PPP
Common Name English
PHENOL, 3-((3R)-1-PROPYL-3-PIPERIDINYL)-
Systematic Name English
(R)-PRECLAMOL
Common Name English
(R)-(+)-3-(3-HYDROXYPHENYL)-N-PROPYLPIPERIDINE
Systematic Name English
Code System Code Type Description
FDA UNII
8L7H229K4I
Created by admin on Sat Dec 16 08:06:56 GMT 2023 , Edited by admin on Sat Dec 16 08:06:56 GMT 2023
PRIMARY
CAS
85976-54-1
Created by admin on Sat Dec 16 08:06:56 GMT 2023 , Edited by admin on Sat Dec 16 08:06:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID101017364
Created by admin on Sat Dec 16 08:06:56 GMT 2023 , Edited by admin on Sat Dec 16 08:06:56 GMT 2023
PRIMARY
PUBCHEM
202478
Created by admin on Sat Dec 16 08:06:56 GMT 2023 , Edited by admin on Sat Dec 16 08:06:56 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
SALT/SOLVATE -> PARENT