N -Methyl-3-piperidyl benzilateLegal status
DE : Anlage I (Authorized scientific use only)
US : Schedule I
(1-Methylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
CAS Number PubChem CID ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.020.031 Formula C 20 H 23 N O 3 Molar mass 325.408 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
Y Key:ZBEILXWHVSVDBN-UHFFFAOYSA-N
Y
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 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, Mepenzolate bromide .
See also [ ]
N-ethyl-3-piperidyl benzilate
3-Quinuclidinyl benzilate
Ditran
References [ ]
^ 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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See also: Receptor/signaling modulators • Nicotinic acetylcholine receptor modulators • Acetylcholine metabolism/transport modulators