1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine

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1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine

IUPAC name 1-Benzyl-4-[2-(diphenylmethoxy)ethyl]piperidine
Identifiers
CAS number	174643-75-5^N
PubChem	9952105
ChemSpider	8127716^Y
ChEMBL	CHEMBL338733^Y
Jmol-3D images	Image 1
SMILES O(C(c1ccccc1)c2ccccc2)CCC4CCN(Cc3ccccc3)CC4
InChI InChI=1S/C27H31NO/c1-4-10-24(11-5-1)22-28-19-16-23(17-20-28)18-21-29-27(25-12-6-2-7-13-25)26-14-8-3-9-15-26/h1-15,23,27H,16-22H2^Y Key: WRSJONWBAYSODC-UHFFFAOYSA-N^Y InChI=1/C27H31NO/c1-4-10-24(11-5-1)22-28-19-16-23(17-20-28)18-21-29-27(25-12-6-2-7-13-25)26-14-8-3-9-15-26/h1-15,23,27H,16-22H2 Key: WRSJONWBAYSODC-UHFFFAOYAC
Properties
Molecular formula	C₂₇H₃₁NO
Molar mass	385.54 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine is a stimulant of the piperidine class which acts as a potent and selective dopamine reuptake inhibitor.^[1]^[2] It is closely related to vanoxerine and GBR-12,935, which in contrast are piperazines.

References

^ Dutta AK, Coffey LL, Reith ME (January 1997). "Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: effect of different aromatic substitutions on their affinity and selectivity". Journal of Medicinal Chemistry 40 (1): 35–43. doi:10.1021/jm960638e. PMID 9016326.
^ Dutta AK, Davis MC, Fei XS, Beardsley PM, Cook CD, Reith ME (January 2002). "Expansion of structure-activity studies of piperidine analogues of 1-[2-(diphenylmethoxy)ethyl]-4-(3-phenylpropyl)piperazine (GBR 12935) compounds by altering substitutions in the N-benzyl moiety and behavioral pharmacology of selected molecules". Journal of Medicinal Chemistry 45 (3): 654–62. doi:10.1021/jm010316x. PMID 11806716.

v t e Stimulants (N06B)

Adamantanes	Adaphenoxate • Adapromine • Amantadine • Bromantane • Chlodantane • Gludantane • Memantine • Midantane

Adenosine antagonists	8-Chlorotheophylline • 8-Cyclopentyltheophylline • 8-Phenyltheophylline • Aminophylline • Caffeine • CGS-15943 • Dimethazan • Paraxanthine • SCH-58261 • Theobromine • Theophylline

Alkylamines	Cyclopentamine • Cypenamine • Cyprodenate • Heptaminol • Isometheptene • Methylhexaneamine • Octodrine • Propylhexedrine • Tuaminoheptane

Arylcyclohexylamines	Benocyclidine • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Phencyclamine • Phencyclidine • Rolicyclidine • Tenocyclidine • Tiletamine

Benzazepines	6-Br-APB • SKF-77434 • SKF-81297 • SKF-82958

Cholinergics	A-84543 • A-366,833 • ABT-202 • ABT-418 • AR-R17779 • Altinicline • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • PHA-543,613 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • SIB-1553A • SSR-180,711 • TC-1698 • TC-1827 • TC-2216 • TC-5619 • Tebanicline • UB-165 • Varenicline • WAY-317,538

Convulsants	Anatoxin-a • Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone

Eugeroics	Adrafinil • Armodafinil • CRL-40941 • Modafinil

Oxazolines	4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone

Phenethylamines	1-(4-Methylphenyl)-2-aminobutane • 1-Phenyl-2-(piperidin-1-yl)pentan-3-one • 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane • 2-Fluoroamphetamine • 2-Fluoromethamphetamine • 2-OH-PEA • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 2,3-MDA • 3-Fluoroamphetamine • 3-Fluoroethamphetamine • 3-Fluoromethcathinone • 3-Methoxyamphetamine • 3-Methylamphetamine • 3,4-DMMC • 4-BMC • 4-Ethylamphetamine • 4-FA • 4-FMA • 4-MA • 4-MMA • 4-MTA • 6-FNE • Alfetamine • α-Ethylphenethylamine • Amfecloral • Amfepentorex • Amfepramone • Amidephrine • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Arbutamine • β-Methylphenethylamine • β-Phenylmethamphetamine • Benfluorex • Benzedrone • Benzphetamine • BDB (J) • BOH (Hydroxy-J) • BPAP • Buphedrone • Bupropion (Amfebutamone) • Butylone • Cathine • Cathinone • Chlorphentermine • Cinnamedrine • Clenbuterol • Clobenzorex • Cloforex • Clortermine • D-Deprenyl • Denopamine • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Dobutamine • DOPA (Dextrodopa, Levodopa) • Dopamine • Dopexamine • Droxidopa • EBDB (Ethyl-J) • Ephedrine • Epinephrine (Adrenaline) • Epinine (Deoxyepinephrine) • Etafedrine • Ethcathinone (Ethylpropion) • Ethylamphetamine (Etilamfetamine) • Ethylnorepinephrine (Butanefrine) • Ethylone • Etilefrine • Famprofazone • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenmetramide • Fenproporex • Flephedrone • Fludorex • Furfenorex • Gepefrine • HMMA • Hordenine • Ibopamine • IMP • Indanylamphetamine • Isoetarine • Isoethcathinone • Isoprenaline (Isoproterenol) • L-Deprenyl (Selegiline) • Lefetamine • Lisdexamfetamine • Lophophine (Homomyristicylamine) • Manifaxine • MBDB (Methyl-J; "Eden") • MDA (Tenamfetamine) • MDBU • MDEA ("Eve") • MDMA ("Ecstasy", "Adam") • MDMPEA (Homarylamine) • MDOH • MDPR • MDPEA (Homopiperonylamine) • Mefenorex • Mephedrone • Mephentermine • Metanephrine • Metaraminol • Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine, Levomethamphetamine) • Methoxamine • Methoxyphenamine • MMA • Methcathinone (Methylpropion) • Methedrone • Methoxyphenamine • Methylone • MMDA • MMDMA • MMMA • Morazone • N-Benzyl-1-phenethylamine • N,N-Dimethylphenethylamine • Naphthylamphetamine • Nisoxetine • Norepinephrine (Noradrenaline) • Norfenefrine • Norfenfluramine • Normetanephrine • Octopamine • Orciprenaline • Ortetamine • Oxilofrine • Paredrine (Norpholedrine, Oxamphetamine, Mycadrine) • PBA • PCA • PHA • Pargyline • Pentorex (Phenpentermine) • Pentylone • Phenatine • Phendimetrazine • Phenmetrazine • Phenpromethamine • Phentermine • Phenylalanine • Phenylephrine (Neosynephrine) • Phenylpropanolamine • Pholedrine • PIA • PMA • PMEA • PMMA • PPAP • Prenylamine • Propylamphetamine • Pseudoephedrine • Radafaxine • Ropinirole • Salbutamol (Albuterol; Levosalbutamol) • Sibutramine • Synephrine (Oxedrine) • Theodrenaline • Tiflorex (Flutiorex) • Tranylcypromine • Tyramine • Tyrosine • Xamoterol • Xylopropamine • Zylofuramine

Piperazines	2C-B-BZP • BZP • CM156 • DBL-583 • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine

Piperidines	1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine • 1-(3,4-Dichlorophenyl)-1-(piperidin-2-yl)butane • 2-Benzylpiperidine • 2-Methyl-3-phenylpiperidine • 3,4-Dichloromethylphenidate • 4-Benzylpiperidine • 4-Methylmethylphenidate • Desoxypipradrol • Difemetorex • Diphenylpyraline • Ethylphenidate • Methylnaphthidate • Methylphenidate (Dexmethylphenidate) • N-Methyl-3β-propyl-4β-(4-chlorophenyl)piperidine • Nocaine • Phacetoperane • Pipradrol • SCH-5472

Pyrrolidines	2-Diphenylmethylpyrrolidine • α-PPP • α-PBP • α-PVP • Diphenylprolinol • MDPPP • MDPBP • MDPV • MPBP • MPHP • MPPP • MOPPP • Naphyrone • PEP • Prolintane • Pyrovalerone

Tropanes	3-CPMT • 3'-Chloro-3α-(diphenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • 4'-Fluorococaine • AHN-1055 • Altropane (IACFT) • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (¹²³I) • Norcocaine • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-105 • RTI-112 • RTI-113 • RTI-117 • RTI-120 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-154 • RTI-171 • RTI-177 • RTI-183 • RTI-193 • RTI-194 • RTI-199 • RTI-202 • RTI-204 • RTI-229 • RTI-241 • RTI-336 • RTI-354 • RTI-371 • RTI-386 • Salicylmethylecgonine • Tesofensine • Troparil (β-CPT, WIN 35,065-2) • Tropoxane • WF-23 • WF-33 • WF-60

Others	1-(Thiophen-2-yl)-2-aminopropane • 2-Amino-1,2-dihydronaphthalene • 2-Aminoindane • 2-Aminotetralin • 2-MDP • 2-Phenylcyclohexylamine • 2-Phenyl-3,6-dimethylmorpholine • 3-Benzhydrylmorpholine • 3,3-Diphenylcyclobutanamine • 5-(2-Aminopropyl)indole • 5-Iodo-2-aminoindane • AL-1095 • Amfonelic acid • Amineptine • Amiphenazole • Atipamezole • Atomoxetine (Tomoxetine) • Bemegride • Benzydamine • BTQ • BTS 74,398 • Camfetamine • Carphedon • Ciclazindol • Cilobamine • Clofenciclan • Cropropamide • Crotetamide • Cypenamine • D-161 • Diclofensine • Dimethocaine • Efaroxan • Etamivan • EXP-561 • Fencamfamine • Fenpentadiol • Feprosidnine • G-130 • Gamfexine • Gilutensin • GSK1360707F • GYKI-52895 • Hexacyclonate • Idazoxan • Indanorex • Indatraline • JNJ-7925476 • JZ-IV-10 • Lazabemide • Leptacline • Levopropylhexedrine • Lomevactone • LR-5182 • Mazindol • Meclofenoxate • Medifoxamine • Mefexamide • Mesocarb • Methastyridone • Methiopropamine • N-Methyl-3-phenylnorbornan-2-amine • Nefopam • Nikethamide • Nomifensine • O-2172 • Oxaprotiline • Phthalimidopropiophenone • PNU-99,194 • Propylhexedrine • PRC200-SS • Rasagiline • Rauwolscine • Rubidium chloride • Setazindol • Tametraline • Tandamine • Trazium • UH-232 • Yohimbine

See also Sympathomimetic amines

Dopaminergics

Receptor ligands

Agonists	Adamantanes: Amantadine Memantine Rimantadine; Aminotetralins: 7-OH-DPAT 8-OH-PBZI Rotigotine UH-232; Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959; Ergolines: Bromocriptine Cabergoline Dihydroergocryptine Lisuride LSD Pergolide; Dihydrexidine derivatives: 2-OH-NPA A-86,929 Ciladopa Dihydrexidine Dinapsoline Dinoxyline Doxanthrine; Others: A-68,930 A-77636 A-412,997 ABT-670 ABT-724 Aplindore Apomorphine Aripiprazole Bifeprunox BP-897 CY-208,243 Dizocilpine Etilevodopa Flibanserin Ketamine Melevodopa Modafinil Pardoprunox Phencyclidine PD-128,907 PD-168,077 PF-219,061 Piribedil Pramipexole Propylnorapomorphine Pukateine Quinagolide Quinelorane Quinpirole RDS-127 Ro10-5824 Ropinirole Rotigotine Roxindole Salvinorin A SKF-89,145 Sumanirole Terguride Umespirone WAY-100,635

Antagonists	Typical antipsychotics: Acepromazine Azaperone Benperidol Bromperidol Clopenthixol Chlorpromazine Chlorprothixene Droperidol Flupentixol Fluphenazine Fluspirilene Haloperidol Loxapine Mesoridazine Methotrimeprazine Nemonapride Penfluridol Perazine Periciazine Perphenazine Pimozide Prochlorperazine Promazine Sulforidazine Sulpiride Sultopride Thioridazine Thiothixene Trifluoperazine Triflupromazine Trifluperidol Zuclopenthixol; Atypical antipsychotics: Amisulpride Asenapine Blonanserin Cariprazine Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Lurasidone Melperone Molindone Mosapramine Olanzapine Paliperidone Perospirone Piquindone Quetiapine Remoxipride Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Antiemetics: AS-8112 Alizapride Bromopride Clebopride Domperidone Metoclopramide Thiethylperazine; Others: Amoxapine Buspirone Butaclamol Ecopipam EEDQ Eticlopride Fananserin L-745,870 Nafadotride Nuciferine PNU-99,194 Raclopride Sarizotan SB-277,011-A SCH-23,390 SKF-83,959 Sonepiprazole Spiperone Spiroxatrine Stepholidine Tetrahydropalmatine Tiapride UH-232 Yohimbine

Reuptake inhibitors

Plasmalemmal

DAT inhibitors

Piperazines: DBL-583
GBR-12,935
Nefazodone
Vanoxerine; Piperidines: BTCP
Desoxypipradrol
Dextromethylphenidate
Difemetorex
Ethylphenidate
Methylnaphthidate
Methylphenidate
Phencyclidine
Pipradrol; Pyrrolidines: Diphenylprolinol
Methylenedioxypyrovalerone (MDPV)
Naphyrone
Prolintane
Pyrovalerone; Tropanes: β-CPPIT
Altropane
Brasofensine
CFT
Cocaine
Dichloropane
Difluoropine
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (¹²³I)
Iometopane
RTI-112
RTI-113
RTI-121
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
Tenocyclidine
Tesofensine
Troparil
Tropoxane
WF-11
WF-23
WF-31
WF-33; Others: Adrafinil
Armodafinil
Amfonelic acid
Amineptine
Benzatropine (Benztropine)
Bromantane
BTQ
BTS-74,398
Bupropion (Amfebutamone)
Ciclazindol
Diclofensine
Dimethocaine
Diphenylpyraline
Dizocilpine
DOV-102,677
DOV-21,947
DOV-216,303
Etybenzatropine (Ethylbenztropine)
EXP-561
Fencamine
Fencamfamine
Fezolamine
GYKI-52,895
Indatraline
Ketamine
Lefetamine
Levophacetoperane
LR-5182
Manifaxine
Mazindol
Medifoxamine
Mesocarb
Modafinil
Nefopam
Nomifensine
NS-2359
O-2172
Pridefrine
Propylamphetamine
Radafaxine
SEP-225,289
SEP-227,162
Sertraline
Sibutramine
Tametraline
Tedatioxetine
Tripelennamine

Vesicular

VMAT inhibitors	Deserpidine Ibogaine Reserpine Tetrabenazine

Releasing agents

Morpholines: Fenbutrazate
Morazone
Phendimetrazine
Phenmetrazine; Oxazolines: 4-Methylaminorex (4-MAR, 4-MAX)
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone; Phenethylamines (also amphetamines, cathinones, phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA)
4-CAB
4-Methylamphetamine (4-MA)
4-Methylmethamphetamine (4-MMA)
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Methylphenethylamine (β-Me-PEA)
Benzodioxolylbutanamine (BDB)
Benzodioxolylhydroxybutanamine (BOH)
Benzphetamine
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
Dimethoxyamphetamine (DMA)
Dimethoxymethamphetamine (DMMA)
Dimethylamphetamine
Dimethylcathinone (Dimethylpropion, metamfepramone)
Ethcathinone (Ethylpropion)
Ethylamphetamine
Ethylbenzodioxolylbutanamine (EBDB)
Ethylone
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
Lophophine (Homomyristicylamine)
Mefenorex
Mephedrone
Methamphetamine (Desoxyephedrine, Methedrine; Dextromethamphetamine
Levomethamphetamine)
Methcathinone (Methylpropion)
Methedrone
Methoxymethylenedioxyamphetamine (MMDA)
Methoxymethylenedioxymethamphetamine (MMDMA)
Methylbenzodioxolylbutanamine (MBDB)
Methylenedioxyamphetamine (MDA, tenamfetamine)
Methylenedioxyethylamphetamine (MDEA)
Methylenedioxyhydroxyamphetamine (MDOH)
Methylenedioxymethamphetamine (MDMA)
Methylenedioxymethylphenethylamine (MDMPEA, homarylamine)
Methylenedioxyphenethylamine (MDPEA, homopiperonylamine)
Methylone
Ortetamine
Parabromoamphetamine (PBA)
Parachloroamphetamine (PCA)
Parafluoroamphetamine (PFA)
Parafluoromethamphetamine (PFMA)
Parahydroxyamphetamine (PHA)
Paraiodoamphetamine (PIA)
Paredrine (Norpholedrine, Oxamphetamine)
Phenethylamine (PEA)
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Tiflorex (Flutiorex)
Tyramine (TRA)
Xylopropamine
Zylofuramine; Piperazines: 2,5-Dimethoxy-4-bromobenzylpiperazine (2C-B-BZP)
Benzylpiperazine (BZP)
Methoxyphenylpiperazine (MeOPP, paraperazine)
Methylbenzylpiperazine (MBZP)
Methylenedioxybenzylpiperazine (MDBZP, piperonylpiperazine); Others: 2-Amino-1,2-dihydronaphthalene (2-ADN)
2-Aminoindane (2-AI)
2-Aminotetralin (2-AT)
4-Benzylpiperidine (4-BP)
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanylaminopropane (IAP)
Indanorex
Isometheptene
Methylhexanamine
Naphthylaminopropane (NAP)
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane (Tuamine)

Allosteric modulators

Quinazolinamines: SoRI-9804 SoRI-20040 SoRI-20041

Enzyme inhibitors

Anabolism

PAH inhibitors	3,4-Dihydroxystyrene

TH inhibitors	3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

AAAD/DDC inhibitors	Benserazide Carbidopa Genistein Methyldopa

Catabolism

MAO inhibitors	Nonselective: Benmoxin Caroxazone Echinopsidine Furazolidone Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Procarbazine Safrazine Tranylcypromine; MAO-A selective: Amiflamine Bazinaprine Befloxatone Befol Brofaromine Cimoxatone Clorgiline Esuprone Harmala alkaloids Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima; MAO-B selective: D-Deprenyl L-Deprenyl (Selegiline) Ladostigil Lazabemide Milacemide Pargyline Rasagiline Safinamide

COMT inhibitors	Entacapone Tolcapone

DBH inhibitors	Disulfiram Dopastin Fusaric acid Nepicastat Tropolone

Others

Precursors	L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)

Cofactors	Ferrous iron (Fe²⁺) Tetrahydrobiopterin Vitamin B₃ (Niacin Nicotinamide → NADPH) Vitamin B₆ (Pyridoxine Pyridoxamine Pyridoxal → Pyridoxal phosphate) Vitamin B₉ (Folic acid → Tetrahydrofolic acid) Vitamin C (Ascorbic acid) Zinc (Zn²⁺)

Others	Activity enhancers: Benzofuranylpropylaminopentane (BPAP) Phenylpropylaminopentane (PPAP); Toxins: Oxidopamine (6-Hydroxydopamine)

List of dopaminergic drugs

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