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4-Benzylpiperidine
Chemical compound
Chemical compound
| Field | Value | |
|---|---|---|
| Verifiedfields | changed | |
| verifiedrevid | 477221136 | |
| IUPAC_name | 4-(phenylmethyl)piperidine | |
| image | 4-Benzylpiperidine Structure.svg | |
| image_class | skin-invert-image | |
| image2 | 4-benzylpiperidine.png | |
| image_class2 | bg-transparent | |
| legal_DE | The NpSG do not apply to this substance, because it is not a 2-Phenylethylamine derivative | |
| legal_UK | PSA | |
| routes_of_administration | ||
| excretion | ||
| CAS_number_Ref | ||
| CAS_number | 31252-42-3 | |
| UNII_Ref | ||
| UNII | JDF1T4667S | |
| PubChem | 31738 | |
| ChemSpiderID_Ref | ||
| ChemSpiderID | 29432 | |
| ChEMBL_Ref | ||
| ChEMBL | 144129 | |
| <!--Chemical data--> | C | 12 |
| H | 17 | |
| N | 1 | |
| smiles | C1CNCCC1CC2=CC=CC=C2 | |
| StdInChI_Ref | ||
| StdInChI | 1S/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2 | |
| StdInChIKey_Ref | ||
| StdInChIKey | ABGXADJDTPFFSZ-UHFFFAOYSA-N |
| elimination_half-life =
4-Benzylpiperidine is a drug and research chemical used in scientific studies. It has been encountered as a designer drug.
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 109nM (DA), 41.4nM (NE), and 5,246nM (5-HT).
It also functions as a weak monoamine oxidase inhibitor (MAOI) ( = 130μM for and 750μM for ).
The drug has a fast onset of action and a short duration.
Synthesis
4-Cyanopyridine can be reacted with toluene to give 4-benzylpyridine. Catalytic hydrogenation of the pyridine ring then completes the synthesis.
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.
References
References
- (2 July 2024). "EMCDDA–Europol 2011 Annual Report on the implementation of Council Decision 2005/387/JHA".
- (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.
- (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.
- (2013). "Photoinduced direct 4-pyridination of C(sp3)–H Bonds". Chemical Science.
- (2001). "e-EROS Encyclopedia of Reagents for Organic Synthesis". John Wiley & Sons.
- Rafael Foguet, et al. {{US patent. 5395841 (1995 to Ferrer Internacional SA).
- Sui Xiong Cai, et al. WO1996002250 (Cocensys Inc, Acea Pharmaceuticals Inc).
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