PRECLAMOL

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 Search

SMILES

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1358119 | https://www.ncbi.nlm.nih.gov/pubmed/6415751 | https://www.ncbi.nlm.nih.gov/pubmed/7990854

(-)-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

Primary Target	Pharmacology	Condition	Potency
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9680248	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1358119	Primary		Not Provided 511	Unknown Approved Use Unknown
Parkinson's disease 232 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7990854	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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	9680248
Preclamol. A "designer drug" in the treatment of advanced Parkinson's disease.	1996	8615177
Motor effects of the partial dopamine agonist (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine (preclamol) in Parkinson's disease.	1994-09	7990854
Pharmacologic properties of (-)-3PPP (preclamol) in man.	1992	1358119
Differential agonist profile of the enantiomers of 3-PPP at striatal dopamine autoreceptors: dependence on extracellular dopamine.	1991-07	1948667

Patents

Sample Use Guides

In Vivo Use Guide

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).

Name

Type

Language

(-)-3PPP

Preferred Name

English

PRECLAMOL

Official 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