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3-Phenylpiperidine

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Pharmaceutical compound

3-Phenylpiperidine
Identifiers
IUPAC name 3-phenylpiperidine
CAS Number	3973-62-4
PubChemCID	107207
ChemSpider	96476
ChEMBL	ChEMBL1196278
CompTox Dashboard(EPA)	DTXSID30871048
ECHA InfoCard	100.021.458
Chemical and physical data
Formula	C₁₁H₁₅N
Molar mass	161.248 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1CC(CNC1)C2=CC=CC=C2
InChI InChI=1S/C11H15N/c1-2-5-10(6-3-1)11-7-4-8-12-9-11/h1-3,5-6,11-12H,4,7-9H2 Key:NZYBILDYPCVNMU-UHFFFAOYSA-N

3-Phenylpiperidine is achemical compound andcyclized phenethylamine.^[1] It can be thought of asβ-phenethylamine with apropyl group connecting theamine and the β position.^[1]

3-Phenylpiperidine is aparent compound of severaldrugs such as thepsychedelic and related drugsLPH-5^[2] andZ3517967757 (Z7757),^[3] theantipsychotic OSU-6162,^[4] and thesigma receptor agonist 3-PPP.^[1]

According toDaniel Trachsel and colleagues in 2013, thepharmacology of 3-phenylpiperidine itself has not been reported, only itschemical synthesis has been described.^[1]^[5] 3-Phenylpiperidine was first described in thescientific literature by 1933.^[1]^[5]

References

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^^a ^b ^c ^d ^eTrachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag.ISBN 978-3-03788-700-4.OCLC 858805226.Das Piperidinring-Positionsisomer 3-Phenylpiperidin (68) enthält die Phenethylamin-Substruktur. Es wurde bis anhin nur synthetisch beschrieben [56]. Das Derivat 69 ist unter dem Namen 3-PPP bekannt. Es ist für seine Affinität zum Sigma-Rezeptor bekannt und wurde Z.B. daraufhin untersucht, inwieweit es die antikonvulsive Wirkung von herkömmlichen Antiepileptika beeinflusst [97]. Zudem bindet es an Dopamin D2-Rezeptoren [98]. Das (+)-Enantiomer wirkt schwach agonistisch und das (-)-Enantiomer antagonistisch [98].
^M Ro Rsted E, Jensen AA, Smits G, Frydenvang K, Kristensen JL (May 2024)."Discovery and Structure-Activity Relationships of 2,5-Dimethoxyphenylpiperidines as Selective Serotonin 5-HT2A Receptor Agonists".Journal of Medicinal Chemistry.67 (9):7224–7244.doi:10.1021/acs.jmedchem.4c00082.PMC 11089506.PMID 38648420.
^Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (June 2024)."AlphaFold2 structures guide prospective ligand discovery".Science.384 (6702). New York, N.Y.: eadn6354.Bibcode:2024Sci...384n6354L.doi:10.1126/science.adn6354.PMC 11253030.PMID 38753765.
^Natesan S, Svensson KA, Reckless GE, Nobrega JN, Barlow KB, Johansson AM, et al. (August 2006). "The dopamine stabilizers (S)-(-)-(3-methanesulfonyl-phenyl)-1-propyl-piperidine [(-)-OSU6162] and 4-(3-methanesulfonylphenyl)-1-propyl-piperidine (ACR16) show high in vivo D2 receptor occupancy, antipsychotic-like efficacy, and low potential for motor side effects in the rat".The Journal of Pharmacology and Experimental Therapeutics.318 (2):810–818.doi:10.1124/jpet.106.102905.PMID 16648369.
^^a ^bWalters LA, McElvain SM (1933)."Piperidine Derivatives. XIII. Phenyl and Phenylalkyl Substituted Piperidinopropyl Benzoates".Journal of the American Chemical Society.55 (11):4625–4629.Bibcode:1933JAChS..55.4625W.doi:10.1021/ja01338a049.ISSN 0002-7863. Retrieved13 July 2025.

External links

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3-Phenylpiperidine - Isomer Design

Phenethylamines

Entactogens:Lophophine
MDPEA
MDMPEA

Amphetamines

Phentermines

Entactogens:MDPH
MDMPH

Others:Cericlamine

Cathinones

Phenylisobutylamines
(and further-extended)

Stimulants:α-Propylphenethylamine
Hexapradol
Phenylisobutylamine (α-ethylphenethylamine)

Catecholamines
(and close relatives)

Cyclized
phenethylamines

Phenylalkylpyrrolidines	α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP Fluorolintane MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
2-Benzylpiperidines (phenidates)	2-Benzylpiperidine 3-Bromomethylphenidate 3-Chloromethylphenidate 3-Methylmethylphenidate 3,4-Dichloro-2-benzylpiperidine 3,4-Dichloroethylphenidate 3,4-Dichloromethylphenidate 4-Bromoethylphenidate 4-Bromomethylphenidate 4-Chloromethylphenidate 4-Fluoroethylphenidate 4-Fluoroisopropylphenidate 4-Fluoromethylphenidate 4-Methyl-2-benzylpiperidine 4-Methylisopropylphenidate 4-Methylmethylphenidate 4-Nitromethylphenidate α-Acetyl-2-benzylpiperidine α-Keto-2-benzylpiperidine CPMBP Desoxypipradrol (2-DPMP) Difemetorex Ethylnaphthidate (HDEP-28) Ethylphenidate Isopropylnaphthidate Isopropylphenidate MDMPH Methylnaphthidate (HDMP-28) Methylphenidate Phacetoperane Pipradrol Propylphenidate Rimiterol Ritalinamide Ritalinic acid SCH-5472 Serdexmethylphenidate
Phenylmorpholines (phenmetrazines)	(2R,3R)-Hydroxybupropion 2-(2,5-Dimethoxy-4-bromophenyl)morpholine 2-Fluorophenmetrazine 2-Methylphenmetrazine 2-Phenylmorpholine 2-Phenyl-3,6-dimethylmorpholine 3-Chlorophenmetrazine (PAL-594) 3-Fluorophenetrazine 3-Fluorophenmetrazine (PAL-593) 3-Methoxyphenmetrazine 3-Methylphenmetrazine (PAL-773) 4-Fluorophenmetrazine (PAL-748) 4-Methylphendimetrazine 4-Methylphenmetrazine (PAL-747) 2C-B-morpholine Fenbutrazate Fenmetramide Flumexadol G-130 Isophenmetrazine Manifaxine Methylenedioxyphenmetrazine Morazone N-Ethylphenmetrazol Naphthylmetrazine (PAL-704) Naphthylmorpholine (PAL-678) Oxaflozane PDM-35 PF-219,061) Phendimetrazine Phenetrazine Phenmetetrazine Phenmetrazine Phenmetrazol Pseudophenmetrazine Radafaxine ((2S,3S)-hydroxybupropion)
Phenyloxazolamines (aminorexes)	3-Methylaminorex 4-Ethylaminorex (4-EAR) 4'-Fluoroaminorex 4-Methylaminorex (4-MAR) 4,4'-Dimethylaminorex (4,4'-DMAR) 2C-B-aminorex 2F-MAR 4B-MAR 4C-MAR 4F-MAR Aminorex Clominorex Cyclazodone Ephedroxane Fenozolone Fluminorex MDMAR Methylenedioxyaminorex (MDAR) N-Methylcyclazodone N,N-Dimethylaminorex Pemoline Thozalinone
Isoquinolines and tetrahydroisoquinolines	Anhalamine Anhalidine Anhalinine Anhalonidine Anhalonine Anhalotine Arizonine Calycotomine Carnegine (pectenine) Corypalline Debrisoquine Deglucopterocereine Deutetrabenazine Diclofensine DOB-CR DOM-CR Esproquin Gigantine Hedycarine Heliamine Hydrastinine Hydrocotarnine Hydrohydrastinine (MDMTHIQ; MDMA-CR) Isoanhalamine Isoanhalidine Isoanhalonidine Isocorypalline Isopellotine Isosalsoline Lemaireocereine Longimammamine Longimammatine Longimammidine Longimammosine Lophocerine Lophophorine Lophotine MDMA-CR Mescalotam N-Methylanhalinine N-Methylheliamine N-Methylisosalsoline N-Methyl-DOM-CR (Beatrice-CR) N-Methyl-THIQ (METH-CR) Nomifensine Norsalsolinol Nortehaunine Norweberine O-Methylanhalonidine O-Methylpellotine Pachycereine Pellotine Perafensine Peyoglutam Peyophorine Peyotine PMMA-CR Quinisocaine Reticuline Salsolidine Salsoline Salsolinol TDIQ (MDTHIQ, MDA-CR) Tehaunine TehaunineN-oxide Tepenine Tetrabenazine Tetrahydroisoquinoline (THIQ; AMPH-CR) Tetrahydropapaveroline Tilisolol Tretoquinol Uberine Valbenazine Weberidine Weberine Zelandopam
2-Aminoindanes	2-Aminoindane (2-AI) 5-IAI Aprindine BFAI BFMAI DHAI DOM-AI ETAI Indanorex Indantadol MDAI MDMAI MEAI (5-MeO-AI) MMAI NM-2-AI PNU-99,194 TAI
2-Aminotetralins	2-Aminotetralin (2-AT) 5-OH-DPAT 6-CAT 7-OH-DPAT 8-OH-DPAT AS-19 CHF-1024 DOM-AT MDAT MDMAT Nolomirole UH-232
Others / unsorted	1-Aminomethylindanes (e.g.,2CB-Ind,AMMI,bromojimscaline,jimscaline) 2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine,3-PPP,OSU-6162 (PNU-96391),LPH-5,LPH-48,Z3517967757 (Z7757)) 6-AB AL-1095 Aminochromes (e.g.,adrenochrome,adrenolutin) Benzazepines (e.g.,fenoldopam,lorcaserin,SCHEMBL5334361) Benzocyclobutenes (e.g.,2CBCB-NBOMe,bromotomscaline,S33005,TCB-2,tomscaline) Benzoxepins (e.g.,BBOX,IBOX,TFMBOX) Butyltolylquinuclidine Camfetamine Cypenamine (trans-2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g.,LSD) Fencamfamin GYKI-52895 HDMP-29 Ivabradine Lumateperone andanalogues (e.g.,IHCH-7079,IHCH-7086,IHCH-7113,ITI-1549) Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI,RU-27849,DEIMDHPCA,DEMPDHPCA,DEMPDHPCA-2C-D,RU-27251) PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA,TMT,tranylcypromine) Phenylpiracetams (e.g.,phenylpiracetam,MRZ-9547,RGPU-95) Tetrahydrobenzopyranylamines (e.g.,CT-5126) Tolazoline Tricyclics (e.g.,AMDA,AMDH,benzoctamine,dizocilpine,SpAMDA) ZC-B