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			{{Short description|Chemical compound}}
	{{DISPLAYTITLE:''N''-Ethyl-3-piperidyl benzilate}}		{{DISPLAYTITLE:''N''-Ethyl-3-piperidyl benzilate}}
	{{drugbox		{{Drugbox
			| Watchedfields = changed
⚫	| verifiedrevid = 400319455
			| drug_name = ''N''-Ethyl-3-piperidyl benzilate
⚫	| IUPAC_name = (1-ethylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
		⚫	| verifiedrevid = 415855071
⚫	| image = Ethylpiperidinylbenzilate.svg
		⚫	| IUPAC_name = (1-ethylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
⚫	| width = 200
		⚫	| image = Ethylpiperidinylbenzilate.svg
		⚫	| width = 200
			<!--Clinical data-->
			| tradename =
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| pregnancy_category =
		⚫	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
		⚫	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
		⚫	| legal_US = Schedule I
			| legal_DE = Anlage I
		⚫	| routes_of_administration =
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| protein_bound =
		⚫	| metabolism =
		⚫	| elimination_half-life =
		⚫	| excretion =
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|correct|CAS}}
		⚫	| CAS_number = 3567-12-2
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 02J52696MZ
		⚫	| ATC_prefix =
		⚫	| ATC_suffix =
		⚫	| PubChem = 62504
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
		⚫	| DrugBank =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 56281		| ChemSpiderID = 56281
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| InChI = 1/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
	| InChIKey = OJYOTLHNSMYONM-UHFFFAOYAT
⚫	| smiles = O=C(OC1CCCN(CC)C1)C(O)(c2ccccc2)c3ccccc3
	| ChEMBL = 342669		| ChEMBL = 342669
			<!--Chemical data-->
		⚫	| C=21 | H=25 | N=1 | O=3
		⚫	| smiles = O=C(OC1CCCN(CC)C1)C(O)(c2ccccc2)c3ccccc3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 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		| StdInChI = 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
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = OJYOTLHNSMYONM-UHFFFAOYSA-N		| StdInChIKey = OJYOTLHNSMYONM-UHFFFAOYSA-N
⚫	| CAS_number = 3567-12-2
⚫	| ATC_prefix =
⚫	| ATC_suffix =
⚫	| PubChem = 62504
⚫	| DrugBank =
⚫	| C=20|H=23|N=1|O=3
	| molecular_weight = 339.43 g/mol
⚫	| bioavailability =
⚫	| protein_bound =
⚫	| metabolism =
⚫	| elimination_half-life =
⚫	| excretion =
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	| pregnancy_US = <!-- A / B / C / D / X -->
⚫	| pregnancy_category=
⚫	| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
⚫	| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
⚫	| legal_US = Schedule I
	| legal_status =
⚫	| routes_of_administration =
	}}		}}
	'''''N''-Ethyl-3-piperidyl benzilate''' ('''JB-318''') is an ] drug related to the ] ].		'''''N''-Ethyl-3-piperidyl benzilate''' ('''JB-318''') is an ] drug related to the ] ].
	''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 ] and ] effects similar to those of plants such as ] and may be used recreationally at low doses, however unpleasant side effects such as ], ] and vomiting, ] and extreme ] tend to make abuse of these kind of drugs uncommon. Both the ''N''-methyl and ''N''-ethyl analogues of 3-piperidyl benzilate are however ] controlled drugs.		''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 ] and ] effects similar to those of plants such as ] and may be used recreationally at low doses; however, unpleasant side effects such as ], ] and vomiting, ] and extreme ] tend to make abuse of drugs of this kind uncommon. In 1960, it was compared to ] for its "]-like ] effects."<ref>{{cite journal | vauthors = Lebovits BZ, Visotsky HM, Ostfeld AM | title = LSD and JB 318: a comparison of two hallucinogens. I. An exploratory study | journal = A.M.A. Archives of General Psychiatry | volume = 2 | issue = 4 | pages = 390–407 | date = April 1960 | pmid = 14415046 | doi = 10.1001/archpsyc.1960.03590100030004 }}</ref>
			Both the ''N''-methyl and ''N''-ethyl analogues of 3-piperidyl benzilate are, however, ] controlled drugs.
⚫	] versions of this drug have been used in scientific research to map the distribution of ] ] 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.<ref>Nishiyama S, Tsukada H, Sato K, Kakiuchi T, Ohba H, Harada N, Takahashi K. Evaluation of PET ligands (+)N-ethyl-3-piperidyl benzilate and (+)N-propyl-3-piperidyl benzilate for muscarinic cholinergic receptors: a PET study with microdialysis in comparison with (+)N-methyl-3-piperidyl benzilate in the conscious monkey brain. ''Synapse''. 2001 Jun 1;40(3):159-69.</ref>
		⚫	] versions of this drug have been used in scientific research to map the distribution of ] ] 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.<ref>{{cite journal | vauthors = Nishiyama S, Tsukada H, Sato K, Kakiuchi T, Ohba H, Harada N, Takahashi K | title = Evaluation of PET ligands (+)N-ethyl-3-piperidyl benzilate and (+)N-propyl-3-piperidyl benzilate for muscarinic cholinergic receptors: a PET study with microdialysis in comparison with (+)N-methyl-3-piperidyl benzilate in the conscious monkey brain | journal = Synapse | volume = 40 | issue = 3 | pages = 159–169 | date = June 2001 | pmid = 11304753 | doi = 10.1002/syn.1038 | s2cid = 19768941 }}</ref>
			], in his book '']'', describes taking JB-318 as part of an experiment at ]: "I was sitting on the 3rd floor and it seemed like nothing was happening at all. And into the room walked a girl from the community with a pitcher of lemonade and she said, would I like some lemonade, and I said that would be great, and she poured the lemonade, and she poured it and she kept pouring and the lemonade went over the side of the glass and fell to the floor and it went across the floor and up the wall and over the ceiling and down the wall and under my pants which got wet and it came back up into the glass—and when it touched the glass the glass disappeared and the lemonade disappeared and the wetness in my pants disappeared and the girl disappeared and I turned around to ] and I said, “Ralph, the most extraordinary thing happened to me,” and Ralph disappeared!"<ref>{{cite book | vauthors = Dass R |title=Remember, now be here, now here be, now be nowhere, now be here, now be here |date=1978 |publisher=Hanuman Foundation |location=New York |isbn=978-0-517-54305-4 |pages=42–43 |url=https://d-pdf.com/book/946/read}}</ref>
	== See also ==		== See also ==
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	== References ==		== References ==
	{{Reflist|2}}		{{Reflist}}
	{{Hallucinogens}}		{{Hallucinogens}}
			{{Muscarinic acetylcholine receptor modulators}}
	{{Cholinergics}}
			{{DEFAULTSORT:Ethyl-3-piperidyl benzilate, N-}}
	]		]
	]		]
			]
			]
			]