N-Ethyl-3-piperidyl benzilate

N-Ethyl-3-piperidyl benzilate

Systematic (IUPAC) name
(1-ethylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
Clinical data
Pregnancy cat.	?
Legal status	Schedule I (US)
Identifiers
CAS number	3567-12-2
ATC code	?
PubChem	CID 62504
ChemSpider	56281 Y
ChEMBL	CHEMBL342669 Y
Chemical data
Formula	C20H23NO3
Mol. mass	339.43 g/mol
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 Y Key:OJYOTLHNSMYONM-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

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 these kind of drugs 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.

See also

• N-methyl-3-piperidyl benzilate
• 3-Quinuclidinyl benzilate
• Ditran