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2-Benzylpiperidine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 2-benzylpiperidine
CAS Number	32838-55-4
PubChem CID	118004
ChemSpider	105447
CompTox Dashboard (EPA)	DTXSID40871372
ECHA InfoCard	100.046.581
Chemical and physical data
Formula	C12H17N
Molar mass	175.27 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES C1CCNC(C1)CC2=CC=CC=C2
InChI InChI=1S/C12H17N/c1-2-6-11(7-3-1)10-12-8-4-5-9-13-12/h1-3,6-7,12-13H,4-5,8-10H2 Key:ITXCORRITGNIHP-UHFFFAOYSA-N
(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, 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-benzylpiperidine is little used as a stimulant, with its main use being as a synthetic intermediate in the manufacture of other drugs.

See also

• 4-Benzylpiperidine
• Benzylpiperazine

References

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 medicinal 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

• Drugs not assigned an ATC code
• Stimulants
• Piperidines