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CAR302282 structure.png
  • (1-methylpiperidin-4-yl) 2-hydroxy-5-methyl-2-phenylhex-5-en-3-ynoate
CAS Number
PubChem CID
Chemical and physical data
Molar mass313.397 g·mol−1
3D model (JSmol)
  • CC(=C)C#CC(C1=CC=CC=C1)(C(=O)OC2CCN(CC2)C)O
  • InChI=1S/C19H23NO3/c1-15(2)9-12-19(22,16-7-5-4-6-8-16)18(21)23-17-10-13-20(3)14-11-17/h4-8,17,22H,1,10-11,13-14H2,2-3H3

CAR-302,282 (302282, NSC-263548, α-(3-Methylbut-1-yn-3-enyl)mandelic acid 1-methyl-4-piperidyl ester) is an anticholinergic deliriant drug,[1][2] invented under contract to Edgewood Arsenal in the 1960s. It is a potent incapacitating agent with an ED50 of 1.2μg/kg and a high central to peripheral effects ratio, and a relatively short duration of action compared to other similar drugs of around 6-10 hours. Despite its favorable properties it was relatively little researched compared to more high profile compounds from the series such as EA-3167 and EA-3580.[3]

See also


  1. ^ Baumgold J, Abood LG, Aronstam R (March 1977). "Studies on the relationship of binding affinity to psychoactive and anticholingergic potency of a group of psychotomimetic glycolates". Brain Research. 124 (2): 331–40. doi:10.1016/0006-8993(77)90889-7. PMID 843950.
  2. ^ US 4465834, Baum BM, Stange H, "Anticholinergic Drugs.", issued 14 August 1984 
  3. ^ 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. p. 320-326. ISBN 978-1-4243-0080-8.