N-Ethyl-3-piperidyl benzilate

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 YesY
ChEMBL CHEMBL342669 YesY
Chemical data
Formula C20H23NO3 
Mol. mass 339.43 g/mol
SMILES eMolecules & PubChem
 YesY(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.[1]

See also

References

  1. ^ Nishiyama S, Tsukada H, Sato K, Kakiuchi T, Ohba H, Harada N, Takahashi K. Evaluation of PET ligands (+)N-[(11)C]ethyl-3-piperidyl benzilate and (+)N-[(11)C]propyl-3-piperidyl benzilate for muscarinic cholinergic receptors: a PET study with microdialysis in comparison with (+)N-[(11)C]methyl-3-piperidyl benzilate in the conscious monkey brain. Synapse. 2001 Jun 1;40(3):159-69.


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