31252-42-3 Usage
Description
4-Benzylpiperidine is a dopamine-selective releaser, characterized as a clear colorless to yellow viscous liquid. It is a potential candidate for treatments for cocaine dependence and has various applications in the synthesis of different types of drugs.
Uses
Used in Chemical Synthesis:
4-Benzylpiperidine is used as a reactant for the synthesis of various compounds, including 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, and antiserotoninergic, antiplatelet, hemorheologic, antiarrhythmic, and antioxidant molecules via nucleophilic substitution.
Used in Corrosion Inhibition:
4-Benzylpiperidine is used as an acid corrosion inhibitor for iron, providing protection against the detrimental effects of acidic environments on the metal.
Used in Pharmaceutical Research:
In the field of pharmaceutical research, 4-Benzylpiperidine is used as a potential utility of dopamine-selective releaser as a treatment for cocaine dependence. It has been studied for its rapid onset and short duration of action in assays of cocaine discrimination, making it a promising candidate for further research and development in this area.
Preparation
4-Benzylpiperidine can be prepared by reacting 4-cyanopyridine with toluene. Catalytic hydrogenation of the pyridine ring then completes the synthesis.
Synthesis Reference(s)
Synthesis, p. 741, 1980 DOI: 10.1055/s-1980-29196
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.
Check Digit Verification of cas no
The CAS Registry Mumber 31252-42-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,1,2,5 and 2 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 31252-42:
(7*3)+(6*1)+(5*2)+(4*5)+(3*2)+(2*4)+(1*2)=73
73 % 10 = 3
So 31252-42-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2/p+1
31252-42-3Relevant articles and documents
Cobalt-bridged secondary building units in a titanium metal-organic framework catalyze cascade reduction of N-heteroarenes
Feng, Xuanyu,Song, Yang,Chen, Justin S.,Li, Zhe,Chen, Emily Y.,Kaufmann, Michael,Wang, Cheng,Lin, Wenbin
, p. 2193 - 2198 (2019/02/20)
We report here a novel Ti3-BPDC metal-organic framework (MOF) constructed from biphenyl-4,4′-dicarboxylate (BPDC) linkers and Ti3(OH)2 secondary building units (SBUs) with permanent porosity and large 1D channels. Ti-OH groups from neighboring SBUs point toward each other with an O-O distance of 2 ?, and upon deprotonation, act as the first bidentate SBU-based ligands to support CoII-hydride species for effective cascade reduction of N-heteroarenes (such as pyridines and quinolines) via sequential dearomative hydroboration and hydrogenation, affording piperidine and 1,2,3,4-tetrahydroquinoline derivatives with excellent activity (turnover number ~ 1980) and chemoselectivity.
Photochemical Cleavage of Benzylic C-N Bond to Release Amines
Wang, Pengfei,Devalankar, Dattatray A.,Lu, Wenya
, p. 6195 - 6200 (2016/08/16)
The 3-(diethylamino)benzyl (DEABn) group has been studied for releasing primary, secondary, and tertiary amines by direct photochemical breaking of the benzylic C-N bond. While photochemical release of primary and secondary amines provides high yields in
Alkali metals in silica gel (M-SG): A new reagent for desulfonation of amines
Nandi, Partha,Redko, Mikhail Y.,Petersen, Kathryn,Dye, James L.,Lefenfeld, Michael,Vogt, Paul F.,Jackson, James E.
supporting information; experimental part, p. 5441 - 5444 (2009/06/18)
(Chemical Equation Presented) A novel method for the desulfonation of secondary amines is described. Alkali metals absorbed into nanostructured silica (M-SG) were found to be useful solid-state reagents for the desuffonation of a range of N,N-disubstituted sulfonamides. M-SG reagents are room-temperature- stable free-flowing powders that retain the chemical reactivity of the parent metal, decreasing the danger and associated cost of using reactive metals.