APPENDIX 5 : CHEMISTRY OF PEYOTE

Alkaloids are found in a number of cacti: Cereus peruvianus, C. pecten aboriginum, Pilocereus sargentianus Orcutt, Phyllocactus ackermanii, P. russelianus, Echinocereus mamil-losus, 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 wilhamsii 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,' while A. lewinii (the mature Lophophora) contains at least nine, as follows:3 Anhaline (CioHisON), Anhala-mine (CliF11503N), Mescaline (CiiH1703N), Anhalonidine (C12H1703N), Anhalonine (CiaH1503N), Lophophorine (Ci3I-11703N), Pellotine (Ci3F13.903N), Anhalinine and Anhali-dine. 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.'

Hordenine was first isolated from A. fissuratum by Heffter in 1894 and shown to be identical with Späth's anhaline from Lophophora in 192o; Heffter isolated pellotine in 1894, mescaline, anhalonidine, anhalonine and lophophorine in 1896, Kauder adding anhalamine is 1899. Capellman collaborated with Heffter on mescaline in 19°5. If Hefter first isolated the Lophophora alkaloids, Späth is to be largely credited with establishing their chemical constitution and synthesizing them: mescaline in 192o, anhalamine in 1921, and anhaloni-dine and pellotine in 1922. Röder in 1922 and Gangl in 1923 collaborated in establishing the chemical constitution of others of the alkaloids.'

1 Tschirsch, Handbuch, 680.

2 Henry (T. A.), The Plant Aklaloids, 194; Moureu, Review, 519; Heffter, Ueber zwei Cacteenalkalotide, 2977; Ueber Pellote, 3o9 ff.; Späth, Ober die Anhalonium; I, Anhalin und Mezcalin, 129; Kunkel, Handbuch, 836; Schumann, Ober giftige Kakteen, 106.

3 Henry (T. A.), loc. cit. The more recently discovered anhalinine and anhalidine are cited from Schultes, Peyote and Plants Used, 134.

4 Rouhier, Monographic, /96, 2o1, 205, 212.

5 Henry (T. A.), The Plant Alkaloids, 194-95; Moureu, Review, 52o; Heffter, Ueber zwei Cacteenalkalokle, 2976; Ueber Pellote, 69-73; Späth, Ueber die Anhalonium: I, Anhalin und Mezcalin, 129, 138-39; II, Die Kon, stitution, 97, /63. Anhalonine has been found in A. jourdanianum (Henry, op. cit., /94; Heffter, Ueber Pellote, 427) which is identical with Lophophora. See Heffter, Ueber zwei Cacteenalkaloicle, 2976-77, also vols. 29: 2/6, 22,3-25, 227; 34: 3oo5, 3oo8, 30/3; Heffter and Capellman, Versuch zur Synthese, 38: 3634-4o; Kauder, Ober Alkaloide, 19o-98. Späth, with Gangl and Röder, Ober de Anhalonium, IV, VI; Kunkel, Handbuch, 836.