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 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]

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