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CS-27349

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
CS-27349
Identifiers
  • (1R,2R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-yl hydroxy(diphenyl)acetate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H25NO3
Molar mass351.446 g·mol−1
3D model (JSmol)
  • CN1C2CC[C@H](C1CC2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O.Cl
  • 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, orL-2-α-tropinyl benzilate, is an experimentalincapacitating agent. It acts as anantagonist tomuscarinic acetylcholine receptors, causingdelirium. It has 37% of the potency of the related compound3-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 fromcocaine alkaloid.[5] On a related note, it is worthy of mention that 2-tropinone has also had use in the synthesis ofisohomoepibatidine andisohomoepiboxidine.[6][7] These are neonicotinoids that were explored as alternatives to epibatidine, which was too toxic for clinical use.

References

[edit]
  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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