3-Phenylpiperidine

3-Phenylpiperidine
Identifiers
	IUPAC name 3-phenylpiperidine;
CAS Number	3973-62-4;
PubChem CID	107207;
ChemSpider	96476;
ChEMBL	ChEMBL1196278;
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 a chemical compound and cyclized phenethylamine.^[1] It can be thought of as β-phenethylamine with a propyl group connecting the amine and the β position.^[1]

3-Phenylpiperidine is a parent compound of several drugs such as the psychedelic and related drugs LPH-5^[2] and Z3517967757 (Z7757),^[3] the antipsychotic OSU-6162,^[4] and the sigma receptor agonist 3-PPP.^[1]

According to Daniel Trachsel and colleagues in 2013, the pharmacology of 3-phenylpiperidine itself has not been reported, only its chemical synthesis has been described.^[1]^[5] 3-Phenylpiperidine was first described in the scientific literature by 1933.^[1]^[5]

References

^ ^a ^b ^c ^d ^e Trachsel 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 ^b Walters 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. Retrieved 13 July 2025.

External links

3-Phenylpiperidine - Isomer Design

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[Trachsel_2013-1] Trachsel 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].

[RoRstedJensenSmits2024-2] 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_2024-3] 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_2006-4] 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.

[Walters_1933-5] Walters 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. Retrieved 13 July 2025.

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See also

References

External links