APPENDIX 5: CHEMISTRY OF PEYOTE
Reading edition
Alkaloids are found in a number of cacti: Cereus peruvianus, C. pecten aboriginum, Pilocereus sargentianus Orcutt, Phyllocactus ackermanii, P. russelianus, Echinocereus mamillosus, Mammillaria cirrhifera, M. uberiformis, M. centricirrha, Anhalonium prismaticum, A. fissuratum,[1] and Lophophora williamsii. Lophophora in its mature state, however, is notable for the number of alkaloids which it contains, nine being known at present.
The long and hotly-disputed botanical question of Anhalonium williamsii versus A. lewinii, beyond its ethnographic significance in accounting the plants “male” and “female,” has a chemical aspect for a time obscuring their botanical identity. A. williamsii (young specimens of Lophophora) contains only the alkaloid Pellotine,[2] while A. lewinii (the mature Lophophora) contains at least nine, as follows:[3] Anhaline (C₁₀H₁₅ON), Anhalamine (C₁₁H₁₅O₃N), Mescaline (C₁₁H₁₇O₃N), Anhalonidine (C₁₂H₁₇O₃N), Anhalonine (C₁₂H₁₅O₃N), Lophophorine (C₁₃H₁₇O₃N), Pellotine (C₁₃H₁₉O₃N), Anhalinine and Anhalidine. Lophophorine is an oily colorless liquid; mescaline crystallizes only in the presence of atmospheric CO₂; and anhalonidine crystallizes imperfectly; the rest are crystalline. Their physiological activity appears to increase with their chemical complexity.[4]
Hordenine was first isolated from A. fissuratum by Heffter in 1894 and shown to be identical with Späth’s anhaline from Lophophora in 1920; Heffter isolated pellotine in 1894, mescaline, anhalonidine, anhalonine and lophophorine in 1896, Kauder adding anhalamine in 1899. Capellman collaborated with Heffter on mescaline in 1905. If Heffter first isolated the Lophophora alkaloids, Späth is to be largely credited with establishing their chemical constitution and synthesizing them: mescaline in 1920, anhalamine in 1921, and anhalonidine and pellotine in 1922. Röder in 1922 and Gangl in 1923 collaborated in establishing the chemical constitution of others of the alkaloids.[5]