Cryptopine is an opium alkaloid. The alkaloids related to cryptopine arise in nature by the oxidation of tetrahydroberberine bases. Cryptopine is one of the minor alkaloids of opium, which occurs in small quantities in certain corydalis and dicentra species. Cryptopine has the composition C21H23O5N and contains one methylenedioxy, one N-methyl, and two methoxyl groups. The reduction of cryptopine methomethylsulphate with sodium amalgam results in Emde reductive opening of the nitrogen-containing ring and a simultaneous reduction of the carbonyl group, the product being the secondary alcohol tetrahydromethylcryptopine C22H29O5N. Dehydration of this to the olefine anhydrotetrahydromethylcryptopine C22H27O4N followed by oxidation leads to a number of products. This chapter discusses the formation of these structures as determined by Hofmann degradation to trimethylamine and the olefine C11H12O.
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