Cuscohygrine

Cuscohygrine is a bis N-methyl pyrrolidine alkaloid found in coca plants. It can also be extracted from plants of the family Solanaceae, including Atropa belladonna and various Datura species. Cuscohygrine usually occurs along with other, more potent alkaloids such as atropine or cocaine.
Cuscohygrine, along with the related metabolite hygrine, was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca leaves.
Cuscohygrine is an oil that can be distilled without decomposition only in vacuum. It is soluble in water. It also forms a crystalline trihydrate which melts at 40–41 °C.

Biosynthesis

Ornithine is methylated to N-methylornithine and when decarboxylated, becomes N-methylputrescine. 4-methylaminobutanal is yielded from the oxidation of the primary amino-group. 4-methylaminobutanal then cyclizes to an N-methyl-1-pyrrolinium salt salt. The condensation of the pyrrolinium salt with acetoacetyl coenzyme A yields hygrine. Finally, the condensation of the hygrine molecule with another molecule of pyrrolidinium salt yields cuscohygrine.