2-Benzylpiperidine

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 one twentieth as 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]

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 Y
CompTox Dashboard (EPA)	DTXSID40871372
ECHA InfoCard	100.046.581
Chemical and physical data
Formula	C12H17N
Molar mass	175.275 g·mol−1
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 Y Key:ITXCORRITGNIHP-UHFFFAOYSA-N Y
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See also

• 4-Benzylpiperidine
• Benzylpiperazine

References

1. Ferris RM, Tang FL (September 1979). "Comparison of the effects of the isomers of amphetamine, methylphenidate and deoxypipradrol on the uptake of l-[3H]norepinephrine and [3H]dopamine 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 (May 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 (August 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 (2004). "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. US 6124317, Bigge CF, Keana JR, Cai SX, Weber E, Woodward R, Lan NC, Guzikowski AP, "2-substituted piperidine analogs and their use as subtype-selective NMDA receptor antagonists."