149649-22-9

Basic information

• Product Name: N-[(1-BUTYL-2-PYRROLIDINYL)METHYL]-4-CYANO-1-METHOXY-2-NAPHTHALENECARBOXAMIDE
• Synonyms: NAFADOTRIDE;N-[(1-BUTYL-2-PYRROLIDINYL)METHYL]-4-CYANO-1-METHOXY-2-NAPHTHALENECARBOXAMIDE
• CAS NO: 149649-22-9
• Molecular Formula: C22H27N3O2
• Molecular Weight: 365.47
• Mol File: 149649-22-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 556.6°Cat760mmHg
• Flash Point: 290.4°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 2.01E-12mmHg at 25°C
• Refractive Index: 1.603
• Storage Temp.: Desiccate at RT
• PKA: 12.84±0.46(Predicted)
• CAS DataBase Reference: N-[(1-BUTYL-2-PYRROLIDINYL)METHYL]-4-CYANO-1-METHOXY-2-NAPHTHALENECARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1-BUTYL-2-PYRROLIDINYL)METHYL]-4-CYANO-1-METHOXY-2-NAPHTHALENECARBOXAMIDE(149649-22-9)
• EPA Substance Registry System: N-[(1-BUTYL-2-PYRROLIDINYL)METHYL]-4-CYANO-1-METHOXY-2-NAPHTHALENECARBOXAMIDE(149649-22-9)

Safety Data

• Hazardous Substances Data: 149649-22-9(Hazardous Substances Data)

Usage

Uses

Nafadotride is a highly potent and competitive dopamine D3 receptor (D3R) antagonist.

Definition

ChEBI: A naphthalenecarboxamide resulting from the formal condensation of the carboxylic acid group of 4-cyano-1-methoxynaphthalene-2-carboxylic acid with the primary amino group of 1-(1-butylpyrrolidin-2-yl]methanamine. It is a highly potent, competitive, prefer ntial dopamine D3 receptor antagonist, centrally active upon systemic administration.

Biological Activity

Highly potent, competitive, preferential dopamine D 3 receptor antagonist. K i values are 0.52, 5, and 269 nM for human cloned D 3 , D 2 and D 4 receptors respectively. Centrally active upon systemic administration.

InChI:InChI=1/C22H27N3O2/c1-3-4-11-25-12-7-8-17(25)15-24-22(26)20-13-16(14-23)18-9-5-6-10-19(18)21(20)27-2/h5-6,9-10,13,17H,3-4,7-8,11-12,15H2,1-2H3,(H,24,26)

Relevant articles and documents

NAPHTHAMIDE DERIVATIVES

The new naphthamide derivatives according to the invention are characterized in that they correspond to the general formula (I), STR1 where X: represents either a hydrogen atom, or a chlorine or bromine atom, or an amino or aminoalkyl group, an aminosulphamoyl group, a sulphur-containing group such as thiocyanate, alkylthio, alkylsulphinyl or alkylsulphonyl, or a methoxy group, or a nitro group, or a cyano group, or an electron-attracting group;Y: represents an alkyl or alkenyl residue;Z: represents the residues originating from 2-aminomethyl-N-alkylpyrrolidine, 2-aminoethyl-N,N-diethylamine, 2-(aminoethyl)morpholine, 2-aminoethyl-N,N-dibutylamine, 4-amino-N-butylpiperidine or 2-(aminoethyl)pyrrolidine;R: a hydrogen or an OCH 3 substituent.These new derivatives may be employed in the preparation of medicinal products intended for use as an antipsychotic, psychostimulatory, anti-autistic or antidepressant agent, an agent for treating Parkinson's disease or an antihypertensive agent.