Cocaine Stereoisomers List of cocaine analogues

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there 8 stereoisomers of cocaine (with internal portion of tropane ring unchanged). not counting mesomers including 1 & 5 8 position bond bridge of tropane system having r- & s- configurations potentially, containing 4 asymmetric carbons, cocaine can counted having many sixteen stereoisomers. geometric constraints imparted bridgehead amine allow 8 created.



where 2d diagrams given structural analogs below not indicate stereochemistry, should assumed share conformation of r-cocaine, unless noted otherwise.


the natural isomerism of cocaine unstable in several ways besides having high degree of lability; instance: c2 carbmethoxy in biosynthesis end-product maintains axial position, can undergo epimerization via saponification obtain former in equatorial position.


the creation of following analogues of cocaine have traditionally required step has utilized 2-cmt intermediate molecular product.





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