76167-58-3

Basic information

• Product Name: 1-BENZO[1,3]DIOXOL-5-YLMETHYL-PIPERIDIN-4-YLAMINE
• Synonyms: 1-BENZO[1,3]DIOXOL-5-YLMETHYL-PIPERIDIN-4-YLAMINE
• CAS NO: 76167-58-3
• Molecular Formula: C₁₃H₁₈N₂O₂
• Molecular Weight: 234.29422
• Mol File: 76167-58-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 343.896°C at 760 mmHg
• Flash Point: 161.783°C
• Appearance: /
• Density: 1.204g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 1-BENZO[1,3]DIOXOL-5-YLMETHYL-PIPERIDIN-4-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZO[1,3]DIOXOL-5-YLMETHYL-PIPERIDIN-4-YLAMINE(76167-58-3)
• EPA Substance Registry System: 1-BENZO[1,3]DIOXOL-5-YLMETHYL-PIPERIDIN-4-YLAMINE(76167-58-3)

Safety Data

• Hazardous Substances Data: 76167-58-3(Hazardous Substances Data)

Usage

Classification

Dopamine receptor agonist

Specificity

Potent and selective agonist for the D3 subtype

Research Applications

Study the function of the dopamine D3 receptor

Therapeutic Potential

Parkinson's disease, schizophrenia, substance abuse disorders

Mechanism of Action

Modulates the mesolimbic dopaminergic system

Current Status

More research needed to understand pharmacological effects and medical applications

InChI:InChI=1/C13H18N2O2/c14-11-3-5-15(6-4-11)8-10-1-2-12-13(7-10)17-9-16-12/h1-2,7,11H,3-6,8-9,14H2

Upstream product

• 57645-58-6 1-benzo[1,3]dioxol-5-ylmethylpiperidin-4-ylamine dihydrochloride 
• 2606-51-1 3,4-Methylenedioxybenzyl bromide 
• 73874-95-0 (piperidin-4-yl)carbamic acid tert-butyl ester 
• 120-57-0 piperonal 
• 934264-70-7 tert-butyl (1-(benzo[d][1,3]dioxol-5-ylmethyl)piperidin-4-yl)carbamate 

Downstream Products

• 76167-77-6 1-piperonyl-4-(2'-pyrimidylamino)piperidine 
• 948993-91-7 2-amino-N-(1-benzo[1,3]dioxol-5-ylmethyl-piperidin-4-yl)-5-methoxy-benzamide 

Relevant articles and documents

Structure-Activity Relationship, Pharmacological Characterization, and Molecular Modeling of Noncompetitive Inhibitors of the Betaine/γ-Aminobutyric Acid Transporter 1 (BGT1)

N-(1-Benzyl-4-piperidinyl)-2,4-dichlorobenzamide 5 (BPDBA) is a noncompetitive inhibitor of the betaine/GABA transporter 1 (BGT1). We here report the synthesis and structure-activity relationship of 71 analogues. We identify 26m as a more soluble 2,4-Cl substituted 3-pyridine analogue with retained BGT1 activity and an improved off-target profile compared to 5. We performed radioligand-based uptake studies at chimeric constructs between BGT1 and GAT3, experiments with site-directed mutated transporters, and computational docking in a BGT1 homology model based on the newly determined X-ray crystal structure of the human serotonin transporter (hSERT). On the basis of these experiments, we propose a binding mode involving residues within TM10 in an allosteric site in BGT1 that corresponds to the allosteric binding pocket revealed by the hSERT crystal structure. Our study provides first insights into a proposed allosteric binding pocket in BGT1, which accommodates the binding site for a series of novel noncompetitive inhibitors.

SUBSTITUTED 1-AMINOPHTHALAZINE DERIVATIVES, PREPARATION THEREOF AND THERAPEUTIC APPLICATION THEREOF

The invention concerns 1-amino-phthalazine derivatives of general formula (I): Wherein A, B, L, R, R1, R2, R3, R4, R5 and R7 are as defined herein. The invention also concerns the preparation of said compounds and their therapeutic use.

Dopaminergic activity in a series of N-substituted 2-aminopyrimidines

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