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

SMILES

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

InChI

InChIKey=HTSNFXAICLXZMA-CYBMUJFWSA-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-/m1/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-n-propylpiperidine ((-)-3-PPP, also known as preclamol) has a dual action towards to dopamine D2 autoreceptor: it activates it and also acts concomitantly as an antagonist at postsynaptic DA receptors. It was shown, that (-)-3PPP/preclamol was a safe drug for study in the treatment of schizophrenia and may have antipsychotic efficacy. Besides, the motor effects of the drug were evaluated in nine patients with Parkinson's disease using a double-blind, placebo-controlled design. However, the small number of patients manifesting a clinically significant response and the frequently inconsistent effects could indicate that this class of agents may have relatively limited clinical utility.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacologic properties of (-)-3PPP (preclamol) in man.
1992
Preclamol. A "designer drug" in the treatment of advanced Parkinson's disease.
1996
The intrinsic activity of (-)-3-PPP vis-à-vis prolactin-suppressing dopamine D2 receptors in transfected GH4C1 cells is dependent on which secretagogue that is used to provoke prolactin release.
1998
Patents

Patents

Sample Use Guides

30-40 mg
Route of Administration: Intramuscular
In Vitro Use Guide
In vitro, both (+)- and (-)-3-PPP (preclamol) 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 17:01:59 GMT 2023
Edited
by admin
on Sat Dec 16 17:01:59 GMT 2023
Record UNII
9V2O6CRQ6Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRECLAMOL
INN  
INN  
Official Name English
(-)-3PPP
Common Name English
(-)-(S)-M-(1-PROPYL-3-PIPERIDYL)PHENOL
Systematic Name English
preclamol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C82251
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID7048453
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
MESH
C026539
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
EVMPD
SUB10012MIG
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
ChEMBL
CHEMBL7549
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
INN
5769
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
PUBCHEM
5311189
Created by admin on Sat Dec 16 17:02:00 GMT 2023 , Edited by admin on Sat Dec 16 17:02:00 GMT 2023
PRIMARY
SMS_ID
100000081422
Created by admin on Sat Dec 16 17:02:00 GMT 2023 , Edited by admin on Sat Dec 16 17:02:00 GMT 2023
PRIMARY
CAS
85966-89-8
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
FDA UNII
9V2O6CRQ6Z
Created by admin on Sat Dec 16 17:01:59 GMT 2023 , Edited by admin on Sat Dec 16 17:01:59 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY