PROPYLNORAPOMORPHINE, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H21NO2
Molecular Weight	295.3755
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN1CCC2=CC=CC3=C2C1CC4=CC=C(O)C(O)=C34

InChI

InChIKey=BTGAJCKRXPNBFI-UHFFFAOYSA-N

InChI=1S/C19H21NO2/c1-2-9-20-10-8-12-4-3-5-14-17(12)15(20)11-13-6-7-16(21)19(22)18(13)14/h3-7,15,21-22H,2,8-11H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/943290 | https://www.ncbi.nlm.nih.gov/pubmed/21163313 | https://www.ncbi.nlm.nih.gov/pubmed/6288408 | https://www.ncbi.nlm.nih.gov/pubmed/6890636

Propylnorapomorphine is a potent and selective D2 receptor agonist. Propylnorapomorphine is used as a tool compound to label dopamine receptors in rodent brain, and elicits dopaminergic behavioural effects. It stimulates motor activity, induces stereotypic behaviour and sexual stimulation. Propylnorapomorphine was investigated in clinical trial against Parkinson's disease and schizophrenia

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24325578 \| https://www.ncbi.nlm.nih.gov/pubmed/943290	Agonist 2678	10.12 null [pKi]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24325578	Binding Agent 1064	8.74 null [pKi]
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/477735 \| https://www.ncbi.nlm.nih.gov/pubmed/12831994	Partial Agonist 290
D(3) dopamine receptor 16 Target ID: P35462 Gene ID: 1814.0 Gene Symbol: DRD3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12831994	Partial Agonist 290

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1107835	Primary		Not Provided 504	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2869745	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Aporphines. 15. Action of aporphine alkaloids on dopaminergic mechanisms in rat brain.	1976 Jan	943290
3H-N-n-propylnorapomorphine: a novel agonist ligand for central dopamine receptors.	1979 Jul 1	477735
Potentiation of the aphrodisiac effect of N-n-propyl-norapomorphine by naloxone.	1982 Jul 9	6288408
Behavioral effects of (-)10,11-methylenedioxy-N-n-propylnoraporphine, an orally effective long-acting agent active at central dopamine receptors, and analogous aporphines.	1982 Oct	6890636
Kinetics of the uptake and distribution of the dopamine D(2,3) agonist (R)-N-[1-(11)C]n-propylnorapomorphine in brain of healthy and MPTP-treated Göttingen miniature pigs.	2003 Jul	12831994
Effects of unilateral 6-OHDA lesions on [3H]-N-propylnorapomorphine binding in striatum ex vivo and vulnerability to amphetamine-evoked dopamine release in rat.	2011 Feb	21163313
Synthesis and characterization of a novel series of agonist compounds as potential radiopharmaceuticals for imaging dopamine D₂/₃ receptors in their high-affinity state.	2014 Jan 23	24325578

Patents

Sample Use Guides

In Vivo Use Guide

In a clinical study against Parkinson's disease, propylnorapomorphine was administered orally. The most effect was observed at doses of 10 to 15 mg six time per day. In rodents, propylnorapomorphine is administered intraperitoneally.

Route of Administration: Other

In Vitro Use Guide

Binding to dopamine D2 receptor was determined using [3H]spiperone as radioligand and HEK293 cells, expressing recombinant human D2. Dose-response curves were converted to Ki values. pKi for propylnorapomorphine is 10.12.

Name

Type

Language

PROPYLNORAPOMORPHINE, (±)-

Common Name

English

10,11-DIHYDROXY-6-PROPYLNORAPORPHINE

Common Name

English

4H-DIBENZO(DE,G)QUINOLINE-10,11-DIOL, 5,6,6A,7-TETRAHYDRO-6-PROPYL-

Systematic Name

English

(±)-N-N-PROPYLNORAPOMORPHINE

Common Name

English

Code System Code Type Description

CAS

57559-68-9