2-Benzylpiperidine

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2-Benzylpiperidine
2-Benzylpiperidine.png
Systematic (IUPAC) name
2-benzylpiperidine
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number 32838-55-4
ATC code None
PubChem CID 118004
ChemSpider 105447 YesY
Chemical data
Formula C12H17N 
Mol. mass 175.27 g/mol
 YesY (what is this?)  (verify)

2-Benzylpiperidine is a stimulant drug of the piperidine class. It is similar in structure to other drugs such as methylphenidate and desoxypipradrol but around 20 times less potent, and while it boosts norepinephrine levels to around the same extent as d-amphetamine,[1] it has very little effect on dopamine levels, with its binding affinity for the dopamine transporter around 175 times lower than for the noradrenaline transporter.[2] 2-benzylpiperidine is little used as a stimulant, with its main use being as a synthetic intermediate in the manufacture of other drugs.[3][4][5]

See also[edit]

References[edit]

  1. ^ Ferris, RM; Tang, FL (1979). "Comparison of the effects of the isomers of amphetamine, methylphenidate and deoxypipradrol on the uptake of l-3Hnorepinephrine and 3Hdopamine by synaptic vesicles from rat whole brain, striatum and hypothalamus". The Journal of Pharmacology and Experimental Therapeutics 210 (3): 422–8. PMID 39160. 
  2. ^ Kim, DI; Deutsch, HM; Ye, X; Schweri, MM (2007). "Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate". Journal of Medical Chemistry 50 (11): 2718–31. doi:10.1021/jm061354p. PMID 17489581. 
  3. ^ Ablordeppey, SY; Fischer, JB; Law, H; Glennon, RA (2002). "Probing the proposed phenyl-A region of the sigma-1 receptor". Bioorganic & Medicinal Chemistry 10 (8): 2759–65. doi:10.1016/S0968-0896(02)00096-2. PMID 12057665. 
  4. ^ Ágai B, Proszenyák A, Tárkányi G, Vida L, Faigl F. Convenient, Benign and Scalable Synthesis of 2- and 4-Substituted Benzylpiperidines. European Journal of Organic Chemistry 2004; 17:3623-3632. doi:10.1002/ejoc.200400215
  5. ^ Christopher F. Bigge, John F. W. Keana, Sui Xiong Cai, Eckard Weber, Richard Woodward, Nancy C. Lan, Anthony P. Guzikowski. 2-substituted piperidine analogs and their use as subtype-selective NMDA receptor antagonists. US Patent 6124317