4-Benzylpiperidine
Chemical compound
From Wikipedia, the free encyclopedia
4-Benzylpiperidine is a drug and research chemical used in scientific studies. It has been encountered as a designer drug.[1]
- DE: The NpSG do not apply to this substance, because it is not a 2-Phenylethylamine derivative
- UK: Under Psychoactive Substances Act
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| ECHA InfoCard | 100.045.926 |
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| Formula | C12H17N |
| Molar mass | 175.275 g·mol−1 |
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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) (IC50 = 130 μM for MAO-A and 750 μM for MAO-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]