EA-3167

EA-3167
Identifiers
	IUPAC name 1-Azabicyclo[2.2.2]octan-8-yl 2-cyclopentyl-2-hydroxy-2-phenylethanoate;
CAS Number	26758-53-2 ;
PubChem CID	33597;
ChemSpider	30995;
ChEMBL	ChEMBL13050;
CompTox Dashboard (EPA)	DTXSID60949567 ;
Chemical and physical data
Formula	C20H29NO3
Molar mass	331.456 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCC(C1)C(C2=CC=CC=C2)(C(=O)OC3CN4CCC3CC4)O;
	InChI InChI=1S/C20H27NO3/c22-19(24-18-14-21-12-10-15(18)11-13-21)20(23,17-8-4-5-9-17)16-6-2-1-3-7-16/h1-3,6-7,15,17-18,23H,4-5,8-14H2; Key:RFXCNPOWSCFJCD-UHFFFAOYSA-N;
	(verify)

EA-3167 is a potent and long-lasting anticholinergic deliriant drug, related to the chemical warfare agent 3-quinuclidinyl benzilate (QNB) and to the bronchodilator drug tiotropium bromide. It was developed under contract to Edgewood Arsenal during the 1960s as part of the US military chemical weapons program, in an attempt to develop non-lethal incapacitating agents. EA-3167 has identical effects to QNB, but is even more potent and longer-lasting, with an effective dose when administered by injection of as little as 2.5 μg/kg (i.e. 0.2 milligrams for an 80 kg person), and a duration of 120–240 hours (5–10 days). However unlike QNB, EA-3167 was never weaponized or manufactured in bulk.

Stereoisomers of EA-3167 have also been synthesized under the codename HL-031120.

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