N-Methyl-3-piperidyl 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 ;
PubChem CID	62495;
ChemSpider	56274 ;
ChEMBL	ChEMBL139948 ;
CompTox Dashboard (EPA)	DTXSID2046258 ;
ECHA InfoCard	100.020.031
Chemical and physical data
Formula	C20H23NO3
Molar mass	325.40 g/mol 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 ; 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]

Methylation of JB-336 gives the Quat salt, Mepenzolate bromide.

References

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.

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[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.

N-Methyl-3-piperidyl benzilate

See also

References