CS-27349

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 ; 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;

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]

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 alterntives to epibatidine, which was too toxic for clinical use.

References

^ Ball JC (2015). "Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate". Military Medical Science Letters. 84 (1): 2–41. doi:10.31482/mmsl.2015.001.
^ Assessment of Potential Long-Term Health Effects on Army Human Test Subjects of Relevant Biological and Chemical Agents, Drugs, Medications and Substances (PDF) (Report). Ho-Chunk Technical Solutions Healthcare Division. February 29, 2016. Archived (PDF) from the original on December 25, 2020.
^ Atkinson ER, McRitchie-Ticknor DD, Harris LS, Archer S, Aceto MD, Pearl J, et al. (December 1983). "Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates". Journal of Medicinal Chemistry. 26 (12): 1772–1775. doi:10.1021/jm00366a023. PMID 6644747.
^ US 3145210, Archer S, Bell MR, "Esters of 2-tropanol", issued 18 August 1964, assigned to Sterling Drug Inc.
^ Zhang C, Lomenzo SA, Ballay CJ, Trudell ML (1 October 1997). "An Improved Synthesis of (+)-2-Tropinone". The Journal of Organic Chemistry. 62 (22): 7888–7889. doi:10.1021/jo9710083.
^ Zhang C, Gyermek L, Trudell ML (August 1997). "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". Tetrahedron Letters. 38 (32): 5619–5622. doi:10.1016/S0040-4039(97)01276-8.
^ Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1775–1778. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.

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[1] Ball JC (2015). "Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate". Military Medical Science Letters. 84 (1): 2–41. doi:10.31482/mmsl.2015.001.

[2] Assessment of Potential Long-Term Health Effects on Army Human Test Subjects of Relevant Biological and Chemical Agents, Drugs, Medications and Substances (PDF) (Report). Ho-Chunk Technical Solutions Healthcare Division. February 29, 2016. Archived (PDF) from the original on December 25, 2020.

[3] Atkinson ER, McRitchie-Ticknor DD, Harris LS, Archer S, Aceto MD, Pearl J, et al. (December 1983). "Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates". Journal of Medicinal Chemistry. 26 (12): 1772–1775. doi:10.1021/jm00366a023. PMID 6644747.

[4] US 3145210, Archer S, Bell MR, "Esters of 2-tropanol", issued 18 August 1964, assigned to Sterling Drug Inc.

[5] Zhang C, Lomenzo SA, Ballay CJ, Trudell ML (1 October 1997). "An Improved Synthesis of (+)-2-Tropinone". The Journal of Organic Chemistry. 62 (22): 7888–7889. doi:10.1021/jo9710083.

[6] Zhang C, Gyermek L, Trudell ML (August 1997). "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". Tetrahedron Letters. 38 (32): 5619–5622. doi:10.1016/S0040-4039(97)01276-8.

[7] Cheng J, Izenwasser S, Zhang C, Zhang S, Wade D, Trudell ML (April 2004). "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters. 14 (7): 1775–1778. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.

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