Alfileramine : A new zanthoxylum alkaloid structurally related to tetrahydrocannabinol |
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| Authors: | Mary A Caolo Frank R Stermitz |
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| Institution: | Department of Chemistry, Colorado State University, Fort Collins, CO 80523, U.S.A. |
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| Abstract: | A new alkaloid, named alfileramine, has been isolated from Zanthoxylum punctatum. It represents the first alkaloid which has a structure closely related to the tetrahydrocannabinols. The structure was assigned based upon 1H and 13C NMR, UV and mass spectroscopy and by relating alfileramine structure to that of the rearranged dihydrobromide salt. The structure of the dihydrobromide was known from X-ray diffraction. A possible biosynthetic pathway from a dehydrocitral equivalent and two molecules of hordenine is suggested. |
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