N-Methyl-3-piperidyl benzilate

N-Methyl-3-piperidyl benzilate

Systematic (IUPAC) name
(1-Methylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
Clinical data
Legal status
Legal status	DE: Anlage I (Controlled) US: Schedule I
Identifiers
CAS Number	3321-80-0
PubChem	CID 62495
ChemSpider	56274
ChEMBL	CHEMBL139948
Chemical data
Formula	C20H23NO3
Molar mass	325.40 g/mol
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 Key:ZBEILXWHVSVDBN-UHFFFAOYSA-N
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N-Methyl-3-piperidyl benzilate (JB-336) is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate.

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]

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. (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): 521–525. doi:10.1016/S0969-8043(97)10155-5. PMID 10070712.