CAR-302,282

CAR-302,282
Identifiers
	IUPAC name (1-methylpiperidin-4-yl) 2-hydroxy-5-methyl-2-phenylhex-5-en-3-ynoate;
CAS Number	62869-67-4;
PubChem CID	44183;
ChemSpider	40202;
ChEMBL	ChEMBL1988426;
CompTox Dashboard (EPA)	DTXSID401337048 ;
Chemical and physical data
Formula	C19H23NO3
Molar mass	313.397 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=C)C#CC(C1=CC=CC=C1)(C(=O)OC2CCN(CC2)C)O;
	InChI 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; Key:HNFSQQPBCHYZKE-UHFFFAOYSA-N;

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]

References

^ 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. S2CID 35326203.
^ US 4465834, Baum BM, Stange H, "Anticholinergic Drugs.", issued 14 August 1984
^ 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.

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[pmid843950-1] 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. S2CID 35326203.

[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.

[1]

[2]

[3]

Identifiers

IUPAC name (1-methylpiperidin-4-yl) 2-hydroxy-5-methyl-2-phenylhex-5-en-3-ynoate
CAS Number	62869-67-4
PubChem CID	44183
ChemSpider	40202
ChEMBL	ChEMBL1988426
CompTox Dashboard (EPA)	DTXSID401337048
Chemical and physical data
Formula	C₁₉H₂₃NO₃
Molar mass	313.397 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=C)C#CC(C1=CC=CC=C1)(C(=O)OC2CCN(CC2)C)O
InChI 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 Key:HNFSQQPBCHYZKE-UHFFFAOYSA-N

CAR-302,282

See also

References