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 109/41.4/5246nM for DA/NE/5HT, respectively . It has a fast onset of action and a short duration. It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.
|CompTox Dashboard (EPA)|
|ECHA InfoCard||100.045.926 |
|Chemical and physical data|
|Molar mass||175.270 g/mol g·mol−1|
|3D model (JSmol)|
4-Cyanopyridine can be reacted with toluene to give 4-benzylpyridine. Catalytic hydrogenation of the pyridine ring then completes the synthesis.
- Negus SS, Baumann MH, Rothman RB, Mello NK, Blough BE (2009). "Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine". J Pharmacol Exp Ther. 329 (1): 272–281. doi:10.1124/jpet.108.143701. PMC 2670586. PMID 19151247.
- Arai Y, Hamamichi N, Kinemuchi H (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". Neurosci. Lett. 70 (2): 255–260. doi:10.1016/0304-3940(86)90473-8. PMID 3490636.
- Hoshikawa, Tamaki; Inoue, Masayuki (2013). "Photoinduced direct 4-pyridination of C(sp3)–H Bonds". Chemical Science. 4 (8): 3118. doi:10.1039/c3sc51080h. ISSN 2041-6520.