2-Benzylpiperidine

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2-Benzylpiperidine
Systematic (IUPAC) name
2-(phenylmethyl)piperidine
Identifiers
CAS number	32838-55-4
ATC code	?
PubChem	118004
Chemical data
Formula	C₁₂H₁₇N
Mol. mass	175.27 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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,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.³⁴

References

^ 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
^ 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
^ 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
^ 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

v • d • e Stimulants

Alkylamines	Cyclopentamine • Geranamine • Heptaminol • Isometheptene • Octodrine • Propylhexedrine • Tuaminoheptane (Tuamine)

Alphapyrrolidinylalkiophenones	α-PPP • MDPPP • MDPV • MPBP • MPHP • MPPP • MOPPP • Pyrovalerone

Cholinergics	ABT-089 • ABT-418 • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • Rivanicline • TC-5619 • Tebanicline • Varenicline

Convulsants	Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone

Eugeroics	Adrafinil • Armodafinil • Carphedon • Modafinil

Phenethylamines	1-Phenyl-2-methylaminobutan-1-one • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 4-Bromomethcathinone • 4-FA • 4-Fluoromethamphetamine • 4-Fluoromethcathinone • 4-Ethylamphetamine • 4-Hydroxyephedrine (Oxilofrine) • 4-Methylamphetamine • 4-Methylmethamphetamine • Mephedrone (4-MMC) • 4-MTA • Alfetamine • Alpha-ethyl-phenethylamine • Amfepentorex • Amphechloral • Amphetamine (Dextroamphetamine, Adderall) • Amphetaminil • Benfluorex • Benzphetamine • Beta-methyl-phenethylamine • Bupropion • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion) • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone • Ephedrine • Epinephrine • Ethcathinone • Ethylamphetamine • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine • Fenproporex • Fludorex • Furfenorex • Levomethamphetamine • Lisdexamfetamine • MDMA (Ecstasy) • Mefenorex • Mephentermine • Methamphetamine • Methcathinone • Methoxyphedrine • Methoxyphenamine • Methylone • Norfenefrine • Octopamine • Ortetamine • Parahydroxyamphetamine • PCA • PIA • PMA • PMEA • PMMA • PPAP • Phendimetrazine • Phenmetrazine • Phenpentermine • Phenpromethamine • Phentermine • Phenylephrine • Phenylpropanolamine • Propylamphetamine • Pseudoephedrine • Selegiline • Synephrine • Tiflorex • Xylopropamine

Phenylaminooxazoles	4-Methyl-aminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone

Piperazines	2C-B-BZP • BZP • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine

Piperidines	2-Benzylpiperidine • Desoxypipradrol • Diphemethoxidine • Ethylphenidate • HDMP-28 • (-)-Methyl-1-methyl-4β-(2-naphthyl)piperidine-3β-carboxylate • Methylphenidate (Dexmethylphenidate) • Nocaine • Phacetoperane (Levofacetoperane) • Pipradrol (Meretran)

Tropanes	3α-Bis-(4-fluorophenyl)methoxytropane • 3α-((4-Chlorophenyl)phenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • Altropane (IACFT) • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • β-CPPIT • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (FPCIT) • Norcocaine • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-112 • RTI-113 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-171 • RTI-177 • RTI-336 • Tesofensine • Troparil (β-CPT, WIN 35, 065-2) • WF-23 • WF-33 • WF-60

Xanthines	Aminophylline • Caffeine • Dimethazan • Paraxanthine • Theobromine • Theophylline

Others	5-(2-Aminopropyl)indole • Amfonelic acid • Amineptine • Amiphenazole • Bemegride • Benzydamine • BPAP • Bromantane • BTQ • BTS 74,398 • Chlodantane • Clofenciclan • Cropropamide • Crotetamide • Cypenamine • Cyprodenate • Diclofensine • Dimethocaine • Diphenylprolinol • Ethamivan • Fencamfamine • Feprosidnine • Gilutensin • GYKI-52895 • Hexacyclonate • Indanorex • Indatraline • Lefetamine • Leptacline • LR-5182 • Manifaxine • Mazindol • Meclofexonate • Mefexamide • Mesocarb • Naphthylisopropylamine • Nikethamide • Nomifensine • O-2172 • Phthalimidopropiophenone • Prolintane • Sibutramine • Tropoxane • Yohimbine • Zylofuramine

See also Sympathomimetic amines

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