Chemistry: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]
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.
References
- ↑ "Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate". Military Medical Science Letters 84 (1): 2–41. 2015. 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 (Report). Ho-Chunk Technical Solutions Healthcare Division. February 29, 2016. https://apps.dtic.mil/sti/pdfs/AD1009505.pdf.
- ↑ "Parasympatholytic (anticholinergic) esters of the isomeric 2-tropanols. 2. Non-glycolates". Journal of Medicinal Chemistry 26 (12): 1772–1775. December 1983. doi:10.1021/jm00366a023. PMID 6644747.
- ↑ Archer S, Bell MR, "Esters of 2-tropanol", US patent 3145210, issued 18 August 1964
- ↑ "An Improved Synthesis of (+)-2-Tropinone". The Journal of Organic Chemistry 62 (22): 7888–7889. 1 October 1997. doi:10.1021/jo9710083.
- ↑ "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. August 1997. doi:10.1016/S0040-4039(97)01276-8.
- ↑ "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. April 2004. doi:10.1016/j.bmcl.2004.01.025. PMID 15026069.
 |  |
