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
Identifiers
  • 4-(phenylmethyl)piperidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.926
Chemical and physical data
FormulaC12H17N
Molar mass175.275 g·mol−1
3D model (JSmol)
  • C1CNCCC1CC2=CC=CC=C2
  • InChI=1S/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2 checkY
  • Key:ABGXADJDTPFFSZ-UHFFFAOYSA-N checkY
 ☒NcheckY (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 [35623-04-2] Patent (Ex 2/3):[5] (Ex 3)[6] This analogue of haloperidol was discovered to have utility in treating both psychosis as well as preventing brain damage by virtue of its NMDA antagonist pharmacology.

See also

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).
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