1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine

Short description: Chemical compound

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine

Identifiers

IUPAC name

* 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine

CAS Number|

* 136534-45-7 Y

PubChem CID|

* 2845469

ChemSpider|

* 2121938

UNII|

* 3LEH2E7AEU

Chemical and physical data
Formula| C18H21ClN2
Molar mass| 300.83 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* ClC1=CC=CC(=C1)N2CCN(CC2)CCC3=CC=CC=C3

InChI

* InChI=1S/C18H21ClN2/c19-17-7-4-8-18(15-17)21-13-11-20(12-14-21)10-9-16-5-2-1-3-6-16/h1-8,15H,9-14H2

* Key:NKMGWZZAFWDLFG-UHFFFAOYSA-N

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is a designer drug of the piperazine class of chemical substances. 3C-PEP is related to meta-cholorophenylpiperazine (mCPP) and phenethylamine that can be thought of as mCPP having a phenylethyl group attached to the nitrogen atom at its 4-position. It was first described in 1994 in a patent disclosing a series of piperazine compounds as sigma receptor ligands.[1] Later, it was discovered to be a highly potent dopamine reuptake inhibitor.[2]

## Contents

* 1 Pharmacology
* 2 Legal status
* 2.1 United States
* 2.2 Canada
* 3 See also
* 4 References

## Pharmacology

3C-PEP is one of the most potent dopamine transporter (DAT) ligand reported to date. It is highly selective for the dopamine transporter (dissociation constant Ki = 0.04 nM) with relatively low affinity for the closely related norepinephrine transporter (NET, Ki = 1107 nM ) and the serotonin transporter (SERT, Ki = 802 nM). In addition, the compound has lower (or no) affinity for D2-like receptor (Ki = 327 nM), serotonin 5-HT2 receptor (Ki = 53 nM), opioid receptor (Ki > 10000 nM), and the PCP/NMDA receptor (Ki > 10000 nM).[2]

With a DAT dissociation constant Ki of 0.04 nM, 3C-PEP is one of the most potent dopamine transporter ligand described to date in the literature. In comparison, cocaine which is a prototypical DAT ligand and reuptake inhibitor has a dissociation constant Ki of 435 nm thus making 3C-PEP about 10,000 times more potent than cocaine as a dopamine transporter inhibitor in vitro.[2]

## Legal status

### United States

3C-PEP is not scheduled at the federal level in the United States ,[3]

### Canada

3C-PEP is not scheduled under the Controlled Drugs and Substances Act.

## See also

* Substituted piperazine
* Etoperidone, nefazodone, and trazodone (structurally related drugs which may also produce mCPP as a metabolite)
* CM156
* Diphenpipenol
* MT-45

## References

1. ↑ Glennon, Richard A. "Sigma receptor ligands and the use thereof". http://www.google.com/patents/US6057371.
2. ↑ 2.0 2.1 2.2 "Chlorophenylpiperazine analogues as high affinity dopamine transporter ligands". Bioorg Med Chem Lett 23 (24): 6020–6922. 2013. doi:10.1016/j.bmcl.2013.09.038. PMID 24211020.
3. ↑ "21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm.

* v
* t
* e

Stimulants

Adamantanes|

* Adapromine
* Amantadine
* Bromantane
* Memantine
* Rimantadine

Adenosine antagonists|

* 8-Chlorotheophylline
* 8-Cyclopentyltheophylline
* 8-Phenyltheophylline
* Aminophylline
* Caffeine
* CGS-15943
* Dimethazan
* Paraxanthine
* SCH-58261
* Theobromine
* Theophylline

Alkylamines|

* Cyclopentamine
* Cypenamine
* Cyprodenate
* Heptaminol
* Isometheptene
* Levopropylhexedrine
* Methylhexaneamine
* Octodrine
* Propylhexedrine
* Tuaminoheptane

Ampakines|

* CX-516
* CX-546
* CX-614
* CX-691
* CX-717
* IDRA-21
* LY-404,187
* LY-503,430
* Nooglutyl
* Org 26576
* PEPA
* S-18986
* Sunifiram
* Unifiram

Arylcyclohexylamines|

* Benocyclidine
* Dieticyclidine
* Esketamine
* Eticyclidine
* Gacyclidine
* Ketamine
* Phencyclamine
* Phencyclidine
* Rolicyclidine
* Tenocyclidine
* Tiletamine

Benzazepines|

* 6-Br-APB
* SKF-77434
* SKF-81297
* SKF-82958

Cholinergics|

* A-84,543
* A-366,833
* ABT-202
* ABT-418
* AR-R17779
* Altinicline
* Anabasine
* Arecoline
* Bradanicline
* 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
* Tebanicline
* UB-165
* Varenicline
* WAY-317,538

Convulsants|

* Anatoxin-a
* Bicuculline
* DMCM
* Flurothyl
* Gabazine
* Haldol
* Pentetrazol
* Picrotoxin
* Strychnine
* Thujone

Eugeroics|

* Adrafinil
* Armodafinil
* CRL-40,940
* CRL-40,941
* Fluorenol
* Modafinil

Oxazolines|

* 4-Methylaminorex
* Aminorex
* Clominorex
* Cyclazodone
* Fenozolone
* Fluminorex
* Pemoline
* Thozalinone

Phenethylamines|

* 1-(4-Methylphenyl)-2-aminobutane
* 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
* 2-Fuoroamphetamine
* 2-Fuoromethamphetamine
* 2-OH-PEA
* 2-Phenyl-3-aminobutane
* 2,3-MDA
* 3-Fuoroamphetamine
* 3-Fluoroethamphetamine
* 3-Fluoromethcathinone
* 3-Methoxyamphetamine
* 3-Methylamphetamine
* 3,4-DMMC
* 4-BMC
* 4-CMC
* 4-Fluoroamphetamine
* 4-Fluoromethamphetamine
* 4-MA
* 4-Methylbuphedrone
* 4-Methylcathinone
* 4-MEAP
* 4-MMA
* 4-Methylpentedrone
* 4-MTA
* 6-FNE
* AL-1095
* Alfetamine
* a-Ethylphenethylamine
* Amfecloral
* Amfepentorex
* Amfepramone
* Amidephrine
* 2-Amino-1,2-dihydronaphthalene
* 2-Aminoindane
* 5-(2-Aminopropyl)indole
* 2-Aminotetralin
* Acridorex
* Amphetamine (Dextroamphetamine, Levoamphetamine)
* Amphetaminil
* Arbutamine
* β-Methylphenethylamine
* β-Phenylmethamphetamine
* Benfluorex
* Benzedrone
* Benzphetamine
* BDB
* BOH
* 3-Benzhydrylmorpholine
* BPAP
* Buphedrone
* Bupropion
* Butylone
* Camfetamine
* Cathine
* Cathinone
* Chlorphentermine
* Cilobamine
* Cinnamedrine
* Clenbuterol
* Clobenzorex
* Cloforex
* Clortermine
* Cypenamine
* D-Deprenyl
* Denopamine
* Dimethoxyamphetamine
* Dimethylamphetamine
* Dimethylcathinone
* Dobutamine
* DOPA (Dextrodopa, Levodopa)
* Dopamine
* Dopexamine
* Droxidopa
* EBDB
* Ephedrine
* Epinephrine
* Epinine
* Etafedrine
* Ethcathinone
* Ethylnorepinephrine
* Ethylone
* Etilamfetamine
* Etilefrine
* Famprofazone
* Fencamfamin
* Fencamine
* Fenethylline
* Fenfluramine (Dexfenfluramine, Levofenfluramine)
* Fenproporex
* Feprosidnine
* Flephedrone
* Fludorex
* Formetorex
* Furfenorex
* Gepefrine
* Hexapradol
* Hexedrone
* HMMA
* Hordenine
* 4-Hydroxyamphetamine
* 5-Iodo-2-aminoindane
* Ibopamine
* Indanylamphetamine
* Iofetamine
* Isoetarine
* Isoethcathinone
* Isoprenaline
* L-Deprenyl (Selegiline)
* Lefetamine
* Lisdexamfetamine
* Lophophine
* MBDB
* MDA (tenamfetamine)
* MDBU
* MDEA
* MDMA (midomafetamine)
* MDMPEA
* MDOH
* MDPR
* MDPEA
* Mefenorex
* Mephedrone
* Mephentermine
* Metanephrine
* Metaraminol
* Mesocarb
* Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
* Methoxamine
* Methoxyphenamine
* MMA
* Methcathinone
* Methedrone
* Methoxyphenamine
* Methylenedioxycathinone
* Methylone
* Mexedrone
* MMDA
* MMDMA
* MMMA
* Morforex
* N,alpha-Diethylphenylethylamine
* N-Ethylbuphedrone
* N-Ethylhexedrone
* N,N-Dimethylphenethylamine
* Naphthylamphetamine
* Nisoxetine
* Norepinephrine
* Norfenefrine
* Norfenfluramine
* Normetanephrine
* L-Norpseudoephedrine
* Octopamine (drug)
* Orciprenaline
* Ortetamine
* Oxifentorex
* Oxilofrine
* PBA
* PCA
* PCMA
* PHA
* Pentorex
* Pentedrone
* Pentylone
* Phenatine
* Phenpromethamine
* Phentermine
* Phenylalanine
* Phenylephrine
* Phenylpropanolamine
* Pholedrine
* PIA
* PMA
* PMEA
* PMMA
* PPAP
* Phthalimidopropiophenone
* Prenylamine
* Propylamphetamine
* Pseudoephedrine
* Ropinirole
* Salbutamol (Levosalbutamol)
* Sibutramine
* Solriamfetol
* Synephrine
* Theodrenaline
* Tiflorex
* Tranylcypromine
* Tyramine
* Tyrosine
* Xylopropamine
* Zylofuramine

Phenylmorpholines|

* 3-Fluorophenmetrazine
* Fenbutrazate
* Fenmetramide
* G-130
* Manifaxine
* Morazone
* Morforex
* Oxaflozane
* PD-128,907
* Phendimetrazine
* Phenmetrazine
* 2-Phenyl-3,6-dimethylmorpholine
* Pseudophenmetrazine
* Radafaxine

Piperazines|

* 2C-B-BZP
* 3C-PEP
* BZP
* CM156
* DBL-583
* GBR-12783
* GBR-12935
* GBR-13069
* GBR-13098
* GBR-13119
* MeOPP
* MBZP
* oMPP
* Vanoxerine

Piperidines|

* 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
* 2-Benzylpiperidine
* 2-Methyl-3-phenylpiperidine
* 3,4-Dichloromethylphenidate
* 4-Benzylpiperidine
* 4-Fluoromethylphenidate
* 4-Methylmethylphenidate
* Desoxypipradrol
* Difemetorex
* Diphenylpyraline
* Ethylnaphthidate
* Ethylphenidate
* Methylnaphthidate
* Isopropylphenidate
* JZ-IV-10
* Methylphenidate (Dexmethylphenidate)
* Nocaine
* Phacetoperane
* Pipradrol
* Propylphenidate
* SCH-5472

Pyrrolidines|

* 2-Diphenylmethylpyrrolidine
* 5-DBFPV
* α-PPP
* α-PBP
* α-PHP
* α-PHPP
* α-PVP
* α-PVT
* Diphenylprolinol
* DMPVP
* FPOP
* FPVP
* MDPPP
* MDPBP
* MPBP
* MPHP
* MPPP
* MOPVP
* MOPPP
* Indapyrophenidone
* MDPV
* Naphyrone
* PEP
* Picilorex
* Prolintane
* Pyrovalerone

Racetams|

* Oxiracetam
* Phenylpiracetam
* Phenylpiracetam hydrazide

Tropanes|

* 4-fluorotropacocaine
* 4'-Fluorococaine
* 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-112
* RTI-113
* RTI-120
* RTI-121 (IPCIT)
* RTI-126
* RTI-150
* RTI-177
* RTI-229
* RTI-336
* RTI-354
* RTI-371
* RTI-386
* Salicylmethylecgonine
* Tesofensine
* Troparil (β-CPT, WIN 35,065-2)
* Tropoxane
* WF-23
* WF-33

Tryptamines|

* 4-HO-αMT
* 4-Methyl-αET
* 4-Methyl-αMT
* 5-Chloro-αMT
* 5-Fluoro-αMT
* 5-MeO-αET
* 5-MeO-αMT
* 5-MeO-DIPT
* 6-Fluoro-αMT
* 7-Methyl-αET
* αET
* αMT

Others|

* 2-MDP
* 3,3-Diphenylcyclobutanamine
* Amfonelic acid
* Amineptine
* Amiphenazole
* Atipamezole
* Atomoxetine
* Bemegride
* Benzydamine
* BTQ
* BTS 74,398
* Centanafadine
* Ciclazindol
* Clofenciclan
* Cropropamide
* Crotetamide
* D-161
* Desipramine
* Diclofensine
* Dimethocaine
* Efaroxan
* Etamivan
* Fenisorex
* Fenpentadiol
* Gamfexine
* Gilutensin
* GSK1360707F
* GYKI-52895
* Hexacyclonate
* Idazoxan
* Indanorex
* Indatraline
* JNJ-7925476
* Lazabemide
* Leptacline
* Lomevactone
* LR-5182
* Mazindol
* Meclofenoxate
* Medifoxamine
* Mefexamide
* Methamnetamine
* Methastyridone
* Methiopropamine
* Naphthylaminopropane
* Nefopam
* Nikethamide
* Nomifensine
* O-2172
* Oxaprotiline
* PNU-99,194
* PRC200-SS
* Rasagiline
* Rauwolscine
* Rubidium chloride
* Setazindol
* Tametraline
* Tandamine
* Thiopropamine
* Thiothinone
* Trazium
* UH-232
* Yohimbine

ATC code: N06B

* v
* t
* e

Dopamine receptor modulators

D1-like|

| Agonists|

* Benzazepines: 6-Br-APB
* Fenoldopam
* SKF-38,393
* SKF-77,434
* SKF-81,297
* SKF-82,958
* SKF-83,959
* Trepipam
* Zelandopam

* Ergolines: Cabergoline
* CY-208,243
* Dihydroergocryptine
* LEK-8829
* Lisuride
* Pergolide
* Terguride

* Dihydrexidine derivatives: A-77636
* A-86929
* Adrogolide (ABT-431, DAS-431)
* Dihydrexidine
* Dinapsoline
* Dinoxyline
* Doxanthrine

* Phenethylamines: BCO-001
* Deoxyepinephrine (N-methyldopamine, epinine)
* Dopexamine
* Etilevodopa
* Ibopamine
* L-DOPA (levodopa)
* Melevodopa
* L-Phenylalanine
* L-Tyrosine
* XP21279

* Others: A-68930
* Apomorphine
* Isocorypalmine
* Nuciferine
* PF-6649751
* PF 6669571
* Propylnorapomorphine
* Rotigotine
* SKF-89,145
* SKF-89,626
* Stepholidine
* Tetrahydropalmatine

|

Antagonists|

* Typical antipsychotics: Butaclamol
* Chlorpromazine
* Chlorprothixene
* Flupentixol (flupenthixol) (+melitracen)
* Fluphenazine
* Loxapine
* Perphenazine (+amitriptyline)
* Pifluthixol
* Thioridazine
* Thiothixene
* Trifluoperazine (+tranylcypromine)
* Zuclopenthixol

* Atypical antipsychotics: Asenapine
* Clorotepine
* Clotiapine
* Clozapine
* DHA-clozapine
* Fluperlapine
* Iloperidone
* Norclozapine
* Norquetiapine
* Olanzapine (++fluoxetine)
* Paliperidone
* Quetiapine
* Risperidone
* Tefludazine
* Zicronapine
* Ziprasidone
* Zotepine

* Others: Berupipam
* Ecopipam
* EEDQ
* Metitepine (methiothepin)
* Odapipam
* Perlapine
* SCH-23390

D2-like|

| Agonists|

* Adamantanes: Amantadine
* Memantine
* Rimantadine

* Aminotetralins: 5-OH-DPAT
* 7-OH-DPAT
* 8-OH-PBZI
* Rotigotine
* UH-232

* Ergolines: Bromocriptine
* Cabergoline
* Dihydroergocryptine
* Epicriptine
* Ergocornine
* Lergotrile
* Lisuride
* LSD
* Pergolide
* Terguride

* Dihydrexidine derivatives: 2-OH-NPA
* Ciladopa
* Dihydrexidine
* Dinoxyline
* N,N-Propyldihydrexidine

* Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
* Dopexamine
* Etilevodopa
* Ibopamine
* L-DOPA (levodopa)
* L-Phenylalanine
* L-Tyrosine
* Melevodopa
* XP21279

* Atypical antipsychotics: Alentemol (U-66444B)
* Aripiprazole (+sertraline)
* Aripiprazole lauroxil
* Bifeprunox
* Brexpiprazole
* Brilaroxazine
* Cariprazine
* F-15063
* Lumateperone
* Norclozapine

* Others: 3-PPP
* A-412997
* ABT-670
* ABT-724
* Adrafinil
* Aplindore
* Apomorphine
* Arketamine
* Armodafinil
* BP-897
* Captodiame
* CP-226,269
* Dizocilpine
* Esketamine
* Flibanserin
* GSK-789,472
* Ketamine
* Mesulergine
* Modafinil
* OSU-6162
* Pardoprunox
* PD-128,907
* PD-168,077
* PF-219,061
* PF-592,379
* Phencyclidine
* Piribedil
* Pramipexole
* Preclamol
* Propylnorapomorphine
* Pukateine
* Quinagolide
* Quinelorane
* Quinpirole
* RDS-127
* Ro10-5824
* Ropinirole
* Roxindole
* Salvinorin A
* SKF-83,959
* Sumanirole
* Talipexole
* Umespirone
* WAY-100,635

|

Antagonists|

* Typical antipsychotics: Acepromazine
* Acetophenazine
* Azaperone
* Benperidol
* Bromperidol
* Butaclamol
* Butaperazine
* Chloracizine
* Chlorproethazine
* Chlorpromazine
* Chlorprothixene
* Ciclindole
* Clopenthixol
* Clothixamide
* Clopimozide
* Droperidol
* Fluacizine
* Fluanisone
* Flucindole
* Fluotracen
* Flupentixol (flupenthixol) (+melitracen)
* Fluphenazine
* Fluprothixene
* Fluspirilene
* Haloperidol
* Homopipramol
* Lenperone
* Levomepromazine (methotrimeprazine)
* Levosulpiride
* Loxapine
* Mesoridazine
* Moperone
* Naranol
* Nemonapride
* Penfluridol
* Perathiepin
* Perazine
* Pericyazine (periciazine)
* Perphenazine (+amitriptyline)
* Piflutixol (pifluthixol)
* Pimozide
* Pipamperone
* Preclamol
* Prochlorperazine
* Promazine
* Prothipendyl
* Spiperone (spiroperidol)
* Sulforidazine
* Sulpiride
* Sultopride
* Teflutixol
* Thiopropazate
* Thioproperazine
* Thioridazine
* Thiothixene
* Timiperone
* Trifluoperazine (+tranylcypromine)
* Triflupromazine
* Trifluperidol
* Zetidoline
* Zuclopenthixol

* Atypical antipsychotics: Amisulpride
* Asenapine
* BL-1020
* Blonanserin
* Carpipramine
* Cinuperone
* Clocapramine
* Clorotepine
* Clotiapine (clothiapine)
* Clozapine
* Cyamemazine
* DHA-clozapine
* Dixyrazine
* Elopiprazole
* Flumezapine
* Fluperlapine
* Gevotroline
* Iloperidone
* Lurasidone
* Mazapertine
* Melperone
* Molindone
* Mosapramine
* Ocaperidone
* Olanzapine (+fluoxetine)
* Paliperidone
* Perospirone
* Piperacetazine
* Pipotiazine
* Piquindone
* Quetiapine
* Remoxipride
* Risperidone
* Sertindole
* Tefludazine
* Tenilapine
* Tiospirone
* Veralipride
* Zicronapine
* Ziprasidone
* Zotepine

* Antiemetics/gastroprokinetics/sedatives: Aceprometazine
* AS-8112
* Alimemazine
* Alizapride
* Benzquinamide
* Bromopride
* Clebopride
* Domperidone
* Eticlopride
* Hydroxyzine
* Itopride
* Metoclopramide
* Metopimazine
* Promethazine
* Thiethylperazine
* Trimethobenzamide

* Antidepressants: Amoxapine
* Nefazodone
* Opipramol
* Propiomazine
* Trimipramine

* Others: 3-PPP
* Alpiropride
* Azapride
* Buspirone
* Desmethoxyfallypride
* EEDQ
* F-15063
* Fallypride
* Fananserin
* Fenfluramine
* GSK-789,472
* Iodobenzamide
* Isocorypalmine
* L-741,626
* L-745,870
* Levofenfluramine
* LEK-8829
* Metergoline
* Metitepine (methiothepin)
* N-Methylspiperone
* Nafadotride
* Nuciferine
* PNU-99,194
* Pridopidine
* Raclopride
* Sarizotan
* SB-277,011-A
* Seridopidine
* Sonepiprazole
* Spiroxatrine
* Stepholidine
* SV-293
* Tetrahydropalmatine
* Tiapride
* UH-232
* Yohimbine

* See also: Receptor/signaling modulators
* Adrenergics
* Serotonergics
* Monoamine reuptake inhibitors
* Monoamine releasing agents
* Monoamine metabolism modulators
* Monoamine neurotoxins

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Original source: https://en.wikipedia.org/wiki/1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine. Read more

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