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N-Methyl-3-piperidyl benzilate

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Chemical compound
Pharmaceutical compound
N-Methyl-3-piperidyl benzilate
Legal status
Legal status
Identifiers
  • (1-Methylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.020.031Edit this at Wikidata
Chemical and physical data
FormulaC20H23NO3
Molar mass325.408 g·mol−1
3D model (JSmol)
  • O=C(OC1CCCN(C)C1)C(O)(c2ccccc2)c3ccccc3
  • 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 checkY
  • Key:ZBEILXWHVSVDBN-UHFFFAOYSA-N checkY
  (verify)

N-Methyl-3-piperidyl benzilate (JB-336 orLBJ) is ananticholinergic drug related to thechemical warfare agent3-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 producesdeliriant andhallucinogenic effects similar to those of plants such asdatura and may be used recreationally at low doses; however, unpleasant side effects such asdysphoria,nausea and vomiting,dizziness and extremedry 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 ofmuscarinicacetylcholine receptors in the brain.[1]

Reaction of JB-336 withmethyl bromide gives the gastrointestinal drugMepenzolate bromide.

See also

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References

[edit]
  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.
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