N-Ethyl-3-piperidyl benzilate

N-Ethyl-3-piperidyl benzilate
Legal status
Legal status	DE: Anlage I (Authorized scientific use only) ; US: Schedule I ;
Identifiers
	IUPAC name (1-ethylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate;
CAS Number	3567-12-2 ;
PubChem CID	62504;
ChemSpider	56281 ;
UNII	02J52696MZ;
ChEMBL	ChEMBL342669 ;
Chemical and physical data
Formula	C21H25NO3
Molar mass	339.43 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OC1CCCN(CC)C1)C(O)(c2ccccc2)c3ccccc3;
	InChI InChI=1S/C21H25NO3/c1-2-22-15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,2,9,14-16H2,1H3 ; Key:OJYOTLHNSMYONM-UHFFFAOYSA-N ;
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N-Ethyl-3-piperidyl benzilate (JB-318) is an anticholinergic drug related to the chemical warfare agent 3-Quinuclidinyl benzilate.

N-Ethyl-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 have been used in scientific research to map the distribution of muscarinic acetylcholine receptors in the brain, however this drug has slightly lower binding affinity than the N-methyl analogue and so is less potent and not so widely used for this application.[1]

References

Nishiyama S, Tsukada H, Sato K, Kakiuchi T, Ohba H, Harada N, Takahashi K (2001). "Evaluation of PET ligands (+)N-[¹¹C]ethyl-3-piperidyl benzilate and (+)N-[¹¹C]propyl-3-piperidyl benzilate for muscarinic cholinergic receptors: a PET study with microdialysis in comparison with (+)N-[¹¹C]methyl-3-piperidyl benzilate in the conscious monkey brain". Synapse. 40 (3): 159–169. doi:10.1002/syn.1038. PMID 11304753.

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[1] Nishiyama S, Tsukada H, Sato K, Kakiuchi T, Ohba H, Harada N, Takahashi K (2001). "Evaluation of PET ligands (+)N-[¹¹C]ethyl-3-piperidyl benzilate and (+)N-[¹¹C]propyl-3-piperidyl benzilate for muscarinic cholinergic receptors: a PET study with microdialysis in comparison with (+)N-[¹¹C]methyl-3-piperidyl benzilate in the conscious monkey brain". Synapse. 40 (3): 159–169. doi:10.1002/syn.1038. PMID 11304753.

N-Ethyl-3-piperidyl benzilate

See also

References