4-Benzylpiperidine

4-Benzylpiperidine is a drug and research chemical used in scientific studies. It acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin. It is most efficacious as a releaser of norepinephrine, with an EC₅₀ of 109 nM (DA), 41.4 nM (NE) and 5246 nM (5-HT).^[1] It has a fast onset of action and a short duration.^[1] It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.^[2]

4-Benzylpiperidine

Legal status
Legal status	DE: The NpSG do not apply to this substance, because it is not a 2-Phenylethylamine derivative UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 4-(phenylmethyl)piperidine
CAS Number	31252-42-3 N
PubChem CID	31738
ChemSpider	29432 Y
UNII	JDF1T4667S
ChEMBL	ChEMBL144129 Y
CompTox Dashboard (EPA)	DTXSID3067603
ECHA InfoCard	100.045.926
Chemical and physical data
Formula	C12H17N
Molar mass	175.275 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCCC1CC2=CC=CC=C2
InChI InChI=1S/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2 Y Key:ABGXADJDTPFFSZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Synthesis

4-Cyanopyridine can be reacted with toluene to give 4-benzylpyridine.^[3] Catalytic hydrogenation of the pyridine ring then completes the synthesis.^[4]

Applications

RMI-10608 is a derivative of 4-benzylpiperidine and analog of haloperidol that was discovered to have potential use in treating psychosis and preventing brain damage by virtue of its NMDA antagonist pharmacology.^[5][6]

See also

• 2-Benzylpiperidine
• Benzylpiperazine
• Tetrahydroisoquinoline

References

1. Negus SS, Baumann MH, Rothman RB, Mello NK, Blough BE (April 2009). "Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine". The Journal of Pharmacology and Experimental Therapeutics. 329 (1): 272–281. doi:10.1124/jpet.108.143701. PMC 2670586. PMID 19151247.
2. Arai Y, Hamamichi N, Kinemuchi H (October 1986). "Time-dependent inhibition of rat brain monoamine oxidase by an analogue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine". Neuroscience Letters. 70 (2): 255–260. doi:10.1016/0304-3940(86)90473-8. PMID 3490636. S2CID 30243106.
3. Hoshikawa T, Inoue M (2013). "Photoinduced direct 4-pyridination of C(sp3)–H Bonds". Chemical Science. 4 (8): 3118. doi:10.1039/c3sc51080h. ISSN 2041-6520.
4. Siegel S (2001). "Rhodium on alumina.". e-EROS Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rr003. ISBN 978-0-471-93623-7. OCLC 1031885332.
5. Rafael Foguet, et al. U.S. patent 5,395,841 (1995 to Ferrer Internacional SA).
6. Sui Xiong Cai, et al. WO1996002250 (Cocensys Inc, Acea Pharmaceuticals Inc).