N-Methyl-3-piperidyl benzilate

N-Methyl-3-piperidyl benzilate (JB-336 or LBJ) is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate.

N-Methyl-3-piperidyl benzilate

Legal status
Legal status	DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (1-Methylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
CAS Number	3321-80-0 Y
PubChem CID	62495
ChemSpider	56274 Y
UNII	3A5HM769QX
ChEMBL	ChEMBL139948 Y
CompTox Dashboard (EPA)	DTXSID2046258
ECHA InfoCard	100.020.031
Chemical and physical data
Formula	C20H23NO3
Molar mass	325.408 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC1CCCN(C)C1)C(O)(c2ccccc2)c3ccccc3
InChI InChI=1S/C20H23NO3/c1-21-14-8-13-18(15-21)24-19(22)20(23,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2-7,9-12,18,23H,8,13-15H2,1H3 Y Key:ZBEILXWHVSVDBN-UHFFFAOYSA-N Y
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N-methyl-3-piperidyl benzilate is less potent and shorter acting than 3-quinuclidyl benzilate, but like 3-QNB its effects on the central nervous system predominate over peripheral effects. It produces deliriant and hallucinogenic effects similar to those of plants such as datura and may be used recreationally at low doses; however, unpleasant side effects such as dysphoria, nausea and vomiting, dizziness and extreme dry mouth tend to make abuse of drugs of this kind uncommon. Both the N-methyl and N-ethyl analogues of 3-piperidyl benzilate are, however, Schedule I controlled drugs.

Radiolabelled versions of this drug are used in scientific research to map the distribution of muscarinic acetylcholine receptors in the brain.^[1]

Methylation of JB-336 gives the quat salt, a Mepenzolate halide.

See also

• N-ethyl-3-piperidyl benzilate
• 3-Quinuclidinyl benzilate
• Ditran

References

1. Takahashi K, Murakami M, Miura S, Iida H, Kanno I, Uemura K (March 1999). "Synthesis and autoradiographic localization of muscarinic cholinergic antagonist (+)N-[11C]methyl-3-piperidyl benzilate as a potent radioligand for positron emission tomography". Applied Radiation and Isotopes. 50 (3): 521–5. doi:10.1016/S0969-8043(97)10155-5. PMID 10070712.