Chemistry:4-Benzylpiperidine
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Short description: Chemical compound
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| Formula | C12H17N |
| Molar mass | 175.275 g·mol−1 |
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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]
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
- ↑ 1.0 1.1 "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. April 2009. doi:10.1124/jpet.108.143701. PMID 19151247.
- ↑ "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. October 1986. doi:10.1016/0304-3940(86)90473-8. PMID 3490636.
- ↑ "Photoinduced direct 4-pyridination of C(sp3)–H Bonds". Chemical Science 4 (8): 3118. 2013. doi:10.1039/c3sc51080h. ISSN 2041-6520.
- ↑ "Rhodium on alumina.". e-EROS Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. 2001. doi:10.1002/047084289X.rr003. ISBN 978-0-471-93623-7. OCLC 1031885332.
- ↑ Rafael Foguet, et al. U.S. Patent 5,395,841 (1995 to Ferrer Internacional SA).
- ↑ Sui Xiong Cai, et al. WO1996002250 (Cocensys Inc, Acea Pharmaceuticals Inc).
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