Sparteine structural properties

Wiewiorowski, M., Pieczonka, G. and Skolik, J. 1977. Futher smdies on the stereochemistry of sparteine, its isomers and derivatives. Part 1. Synthesis, structure and properties of 16,17-endo-methylene-lupaninium perchlorate, 17 3-methyllupanine and 17(3-methyl sparteine. Journal of Molecular Structure, 40 233. 

Marion and Fenton found that its properties were closely related to those of sparteine, from which it was difficult to separate the alkaloid. In common with sparteine, pusilline formed a monoperchlorate which crystallized from aqueous solution only after the addition of a little ammonia. Pusilline was found to contain one methylimino group, and it formed a methiodide which did not undergo the Hofmann degradation but was reconverted to the original base. On the basis of these facts, one probable structural formula for pusilline would be CXIV. It appears that two compounds previously described as the alkaloids nonalupine (90) and spathulatine (90, 108) are in essence derivatives of pusilline (309). 

Sparteine is an alkaloid obtained from lupin beans with antiarrhythmic and oxytocic properties. It has a tetracyclic aliphatic structure with two tertiary alicyclic nitrogens. Since sparteine does not contain a chromophore, it cannot be detected with UV or FL. Therefore, Moncrieff (1990) developed a method of detecting sparteine, and its dehydro metabolites, in urine with... 

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