EA-3580

EA-3580
Identifiers
	IUPAC name (1-methylpiperidin-4-yl) 2-cyclobutyl-2-hydroxy-2-phenylacetate;
CAS Number	54390-94-2 ;
PubChem CID	171342;
ChemSpider	149791;
UNII	RF3SNA5PA2;
CompTox Dashboard (EPA)	DTXSID30969510 ;
Chemical and physical data
Formula	C18H25NO3
Molar mass	303.402 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c3ccccc3C(O)(C2CCC2)C(=O)OC1CCN(C)CC1;
	InChI InChI=1S/C18H25NO3/c1-19-12-10-16(11-13-19)22-17(20)18(21,15-8-5-9-15)14-6-3-2-4-7-14/h2-4,6-7,15-16,21H,5,8-13H2,1H3; Key:LOBGXFLATZQVKC-UHFFFAOYSA-N;
	(verify)

EA-3580 is a potent anticholinergic deliriant drug with a fairly long duration of action, related to the chemical warfare agent 3-Quinuclidinyl benzilate (QNB). It was developed under contract to Edgewood Arsenal during the 1960s as part of the US military chemical weapons program, during research to improve upon the properties of earlier agents such as QNB.

EA-3580 is closely related to the similar compound EA-3443, and has similar potency and high central to peripheral effects ratio, but with a duration of action around half as long, although effects of EA-3580 can still persist for 24 hours or more following high doses.^[1]^[2]

References

^ National Research Council (US) Panel on Anticholinesterase Chemicals; National Research Council (US) Panel on Anticholinergic Chemicals (1982). Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents. Vol. 1. The National Academies Press. pp. 207–211. doi:10.17226/740. ISBN 978-0-309-07759-0. PMID 25032448. {{cite book}}: |work= ignored (help)
^ Ketchum JS (2006). Chemical Warfare Secrets Almost Forgotten. A Personal Story of Medical Testing of Army Volunteers with Incapacitating Chemical Agents During the Cold War. ChemBooks Inc. ISBN 978-1-4243-0080-8.