CS-27349

{{Short description|Chemical compound}}

{{drugbox

| drug_name = CS-27349

| image = CS-27349.svg

| index2_label=HCl

| CAS_number = 64471-12-1

| CAS_number2 = 64520-33-8

| CAS_number_Ref = {{Cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RD1A447UC0

| ChemSpiderID = 143123

| ChemSpiderID2 = 57264798

| DTXSID2 = DTXSID90983151

| PubChem = 3049185

| PubChem2 = 3049184

| ChEMBL = 298138

| SMILES = CN1C2CC[C@H](C1CC2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O.Cl

| StdInChI = 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

| StdInChIKey=LSJGAYNIIMEDLR-SOAGJPPSSA-N

| IUPAC_name = (1R,2R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-yl hydroxy(diphenyl)acetate

| smiles = CN1C2CC[C@H](C1CC2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O

| C=22 | H=25 | N=1 | O=3

}}

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.{{cite journal |journal=Military Medical Science Letters |title=Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate | vauthors = Ball JC |doi=10.31482/mmsl.2015.001 |volume=84 |issue=1 |pages=2–41 |date=2015 |doi-access=free }} It has not been in use since the 1970s, and there have been no publications about its effects or long-term toxicology since then.{{cite report |date=February 29, 2016 |publisher=Ho-Chunk Technical Solutions Healthcare Division |url=https://apps.dtic.mil/sti/pdfs/AD1009505.pdf |archive-url=https://web.archive.org/web/20201225082917/https://apps.dtic.mil/sti/pdfs/AD1009505.pdf |url-status=live |archive-date=December 25, 2020 |title=Assessment of Potential Long-Term Health Effects on Army Human Test Subjects of Relevant Biological and Chemical Agents, Drugs, Medications and Substances}}

Reference:{{cite journal | vauthors=((Atkinson, E. R.)), ((McRitchie-Ticknor, D. D.)), ((Harris, L. S.)), ((Archer, S.)), ((Aceto, M. D.)), ((Pearl, J.)), ((Luduena, F. P.)) | journal=Journal of Medicinal Chemistry | title=Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates | volume=26 | issue=12 | pages=1772–1775 | date= December 1983 | doi=10.1021/jm00366a023}} Patent:Sydney Archer, Bethlehem, and Malcoin R. Bell, US3145210 (1964 to Sterling Drug Inc.).

It is interesting to notice that 2-tropinone is made from cocaine alkaloid.{{cite journal | vauthors=((Zhang, C.)), ((Lomenzo, S. A.)), ((Ballay, C. J.)), ((Trudell, M. L.)) | journal=The Journal of Organic Chemistry | title=An Improved Synthesis of (+)-2-Tropinone | volume=62 | issue=22 | pages=7888–7889 | date=1 October 1997 | doi=10.1021/jo9710083}} On a related note, it is worthy of mention that 2-tropinone has also had use in the synthesis of isohomoepibatidine and isohomoepiboxidine.{{cite journal | vauthors=((Zhang, C.)), ((Gyermek, L.)), ((Trudell, M. L.)) | journal=Tetrahedron Letters | title=Synthesis of optically pure epibatidine analogs: (1R, 2R, 5S)-2β-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane and (1R, 2S, 5S)-2α-(2-chloro-5-pyridinyl)-8-azabicyclo[3.2.1]octane from (−)-cocaine | volume=38 | issue=32 | pages=5619–5622 | date= August 1997 | doi=10.1016/S0040-4039(97)01276-8}}{{cite journal | vauthors=((Cheng, J.)), ((Izenwasser, S.)), ((Zhang, C.)), ((Zhang, S.)), ((Wade, D.)), ((Trudell, M. L.)) | journal=Bioorganic & Medicinal Chemistry Letters | title=Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes | volume=14 | issue=7 | pages=1775–1778 | date= April 2004 | doi=10.1016/j.bmcl.2004.01.025}} These are neonicotinoids that were explored as alterntives to epibatidine, which was too toxic for clinical use.