4-Benzylpiperidine

Chemical Properties

clear colourless to yellow viscous liquid.

Uses

4-Benzylpiperidine was studied as acid corrosion inhibitor for iron. It was also used to study potential utility of dopamine-welective releaser as a treatment for cocaine dependence. In an assay of cocaine discrimination, 4-Benzylpiperidine had the most rapid onset and shortest duration of action.

Preparation

4-Benzylpiperidine can be prepared by reacting 4-cyanopyridine with toluene. Catalytic hydrogenation of the pyridine ring then completes the synthesis.

Application

Reactant for synthesis of:
Antiproliferatives
GABA uptake inhibitors
Pyridines
Histamine H3 antagonists
Multipotent drugs with cholinergic and neuroprotective properties for the treatment of Alzheimer′s and neuronal vascular diseases
Antiserotoninergic, antiplatelet, hemorheologic, antiarrythmic and antioxidant molecules via nucleophilic substitution

Synthesis Reference(s)

Synthesis, p. 741, 1980 DOI: 10.1055/s-1980-29196

General Description

4-Benzylpiperidine is dopamine-selective releaser. It is a potential candidate for treatments for cocaine dependence.

Biochem/physiol Actions

4-Benzylpiperidine inhibits the activity of rat brain monoamine oxidase-A and -B, with IC50 values of 0.02 mM and 2 mM respectively. It acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin. It is most efficacious as a releaser of norepinephrine, with an ec50 of 109/41.4/5246nM for DA/NE/5HT, respectively . It has a fast onset of action and a short duration. It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.