2-Benzylpiperidine

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IUPAC_name = 2-(phenylmethyl)piperidine


CAS_number = 32838-55-4
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PubChem = 118004
DrugBank =
C=12|H=17|N=1
molecular_weight = 175.27 g/mol
smiles = C1CCNC(C1)CC2=CC=CC=C2
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2-Benzylpiperidine is a stimulant drug. It is similar in structure to other drugs such as methylphenidate and desoxypipradrol but around 20 times less potent, and while it boosts noradrenaline levels to around the same extent as dexamphetamine, [Ferris RM, Tang FL. 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. "Journal of Pharmacology and Experimental Therapeutics". 1979 Sep;210(3):422-8. PMID 39160] 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. [Kim DI, Deutsch HM, Ye X, Schweri MM. Synthesis and pharmacology of site-specific cocaine abuse treatment agents: restricted rotation analogues of methylphenidate. "Journal of Medicinal Chemistry". 2007 May 31;50(11):2718-31. PMID 17489581] 2-benzylpiperidine is little used as a stimulant, with its main use being as a synthetic intermediate in the manufacture of other drugs. [Ablordeppey SY, Fischer JB, Glennon RA. Probing the proposed phenyl-A region of the sigma-1 receptor. "Bioorganic and Medicinal Chemistry". 2002 Aug;10(8):2759-65. PMID 12057665] [ [http://www.google.com/patents?id=1H8FAAAAEBAJ&dq=6124317 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] ]

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