4-Benzylpiperidine

4-Benzylpiperidine
Legal status
Legal status
Identifiers
  • 4-(phenylmethyl)piperidine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.926 Edit this at Wikidata
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)

4-Benzylpiperidine is a drug and research chemical used in scientific studies. It has been encountered as a designer drug.[1]

Pharmacology

4-Benzylpiperidine 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 5,246 nM (5-HT).[2]

It also functions as a weak monoamine oxidase inhibitor (MAOI) (IC50Tooltip half-maximal inhibitory concentration = 130 μM for MAO-ATooltip monoamine oxidase A and 750 μM for MAO-BTooltip monoamine oxidase B).[3]

The drug has a fast onset of action and a short duration.[2]

Synthesis

4-Cyanopyridine can be reacted with toluene to give 4-benzylpyridine.[4] Catalytic hydrogenation of the pyridine ring then completes the synthesis.[5]

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.[6][7]

See also

References

  1. ^ "EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA". www.euda.europa.eu. 2 July 2024. Retrieved 9 December 2024.
  2. ^ a b 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Rafael Foguet, et al. U.S. patent 5,395,841 (1995 to Ferrer Internacional SA).
  7. ^ Sui Xiong Cai, et al. WO1996002250 (Cocensys Inc, Acea Pharmaceuticals Inc).