CS-27349

CS-27349, or L-2-α-tropinyl benzilate, is an experimental incapacitating agent. It acts as an antagonist to muscarinic acetylcholine receptors, causing delirium. It has 37% of the potency of the related compound 3-quinuclidinyl benzilate (BZ) in producing peripheral effects, but 85% of the potency in producing central effects. The mean dose required to incapacitate subjects was 1.2 times that of BZ.^[1] It has not been in use since the 1970s, and there have been no publications about its effects or long-term toxicology since then.^[2]

CS-27349

Identifiers
IUPAC name (1R,2R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-yl hydroxy(diphenyl)acetate
CAS Number	64471-12-1 Y HCl: 64520-33-8
PubChem CID	3049185 HCl: 3049184
ChemSpider	143123 HCl: 57264798
UNII	RD1A447UC0
ChEMBL	ChEMBL298138
CompTox Dashboard (EPA)	DTXSID70983033 HCl: DTXSID90983151
Chemical and physical data
Formula	C22H25NO3
Molar mass	351.446 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C2CC[C@H](C1CC2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O.Cl
InChI InChI=1S/C22H25NO3/c1-23-18-12-14-19(23)20(15-13-18)26-21(24)22(25,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-20,25H,12-15H2,1H3/t18?,19?,20-/m1/s1 Key:LSJGAYNIIMEDLR-SOAGJPPSSA-N

Reference:^[3] Patent:^[4]

It is interesting to notice that 2-tropinone is made from cocaine alkaloid.^[5] On a related note, it is worthy of mention that 2-tropinone has also had use in the synthesis of isohomoepibatidine and isohomoepiboxidine.^[6][7] These are neonicotinoids that were explored as alternatives to epibatidine, which was too toxic for clinical use.