4-Benzylpiperidine

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

4-Benzylpiperidine

Legal status
Legal status	DE: The NpSG do not apply to this substance, because it is not a 2-Phenylethylamine derivative UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 4-(phenylmethyl)piperidine
CAS Number	31252-42-3 N
PubChem CID	31738
ChemSpider	29432 Y
UNII	JDF1T4667S
ChEMBL	ChEMBL144129 Y
CompTox Dashboard (EPA)	DTXSID3067603
ECHA InfoCard	100.045.926
Chemical and physical data
Formula	C12H17N
Molar mass	175.275 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1CNCCC1CC2=CC=CC=C2
InChI InChI=1S/C12H17N/c1-2-4-11(5-3-1)10-12-6-8-13-9-7-12/h1-5,12-13H,6-10H2 Y Key:ABGXADJDTPFFSZ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

• 2-Benzylpiperidine
• Benzylpiperazine
• Tetrahydroisoquinoline