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2-Benzylpiperidine
Chemical compound From Wikipedia, the free encyclopedia
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2-Benzylpiperidine is a stimulant drug of the arylpiperidine family. It is similar in structure to certain other stimulants such as methylphenidate and desoxypipradrol. However, it is far less potent as a monoamine reuptake inhibitor in comparison.[1][2][3] The drug is little used as a stimulant, with its main use being as a synthetic intermediate in the manufacture of other drugs.[4][5][6]
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Pharmacology
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The affinity (Ki) of 2-benzylpiperidine for the dopamine transporter (DAT) has been reported to be 6,360 nM and its functional inhibition (IC50) of the DAT has been reported to be 3,780 to 8,800 nM.[1][2][3] These values were 85-fold and 53- to 38-fold lower than those of methylphenidate, respectively.[1][2][3] It produced 36% inhibition of binding to the norepinephrine transporter (NET) and 22% inhibition of binding to the serotonin transporter (SERT) at a concentration of 10,000 nM.[3] However, 2-phenylpiperidine might have actually been assayed by mistake in one of the two studies that reported the preceding values, and so some of the values might be incorrect.[1] In another older study, 2-benzylpiperidine was reported to be similarly potent to dextroamphetamine in terms of norepinephrine reuptake inhibition.[7]
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Analogs
Derivatives of 2-benzylpiperidine, such as the cathinone-like derivative α-keto-2-benzylpiperidine and its 4-methyl, 4-halo, and 3,4-dichloro analogues, have been synthesized and have been found to be much more potent as dopamine reuptake inhibitors.[1] Another analogue of 2-benzylpiperidine, 3-phenylpiperidine, is also more potent as a monoamine reuptake inhibitor in comparison, with higher affinities for the monoamine transporters and ~8-fold higher functional inhibition of the DAT.[3]
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References
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