How did the experimental conditions of Smith and Timmis (ST), in which ergine was
produced from ergotinine, differ from those of Jacobs and Craig (JC), in which lysergic acid
was produced from ergotinine? Fundamentally, the difference was a matter of concentration
and temperature. ST refluxed ergotinine for one hour in a 1.0 M solution of potassium
hydroxide (KOH) in methanol, which boils at 65° C, while JC refluxed ergotinine for an hour
in a 1.4 M solution of KOH in water, which of course boils at 100° C. The reason that ST
used methanol is that pure crystalline ergotinine
21
is insoluble in water and unreactive even in
boiling aqueous KOH. JC found that the resinous material remaining after ergotinine was
rapidly dissolved in methanolic KOH and then evaporated would slowly dissolve with
liberation of ammonia in boiling aqueous 1.4 M KOH. Martínková, Kren, et al. have been
able to maximize the production of ergine/isoergine from ergotamine by using a less
concentrated solution of KOH. They produce a mixture consisting principally of ergine and
isoergine (total: 10.3 g) with relatively small amounts of lysergic acid/isolysergic acids (total:
1.65 g) from 30 g of ergotamine by refluxing for two hours in a 0.60 M solution of KOH, the
solvent being a 1:3 mixture of water:ethyl alcohol.
22
These results can be compared to a
standard procedure for producing lysergic acid from ergotamine as given in Shulgin’s
TIHKAL, where 3.5 g lysergic acid is obtained by stirring 10 g ergotamine in a 1.2 M aqueous
KOH at 70° C for 3 hours.
23
We suggest that conditions of solubility, pH, and temperature which would be equivalent
in effect to ST’s process, and result in the conversion of ergot to ergine, could be readily
obtained by boiling crude ergot for several hours in water to which the ashes of wood or
other plant material, perhaps barley, had been added. These are, of course, conditions easily
achieved by the hierophants of Eleusis. Why would these conditions produce ergine? Wood
ash contains potassium carbonate (pearlash), a strong base which for millennia was the usual
material used to produce soap from animal or vegetable fats — an hydrolysis process
(saponification) almost identical to the hydrolysis of the amide bonds of ergot. Wood ash has
a pH of about 12, while the 0.60 M KOH used by MK has a pH of almost 14. But the Greek
priests would have employed water as a solvent, since distilled methanol or ethanol was then
unknown, and the resulting higher temperatures (and quite likely longer cooking times, which
would tend to concentrate both product and alkali reagent) would compensate for the less
concentrated base. As for the solubility problem encountered by ST and JC, we suggest that it
would not obtain when crude ergot was used instead of crystalline ergotinine. This is because
crude ergot contains from 30-35% fatty acids
24
which would both solubilize the ergot
alkaloids of their own accord and even more so by virtue of the micelles formed when these
fats were saponified by the hot pearlash.
25
Why would the hierophants consider ashes as a suitable ingredient in a sacred potion?
We suggest the possibility that some sort of symbolism involving the resurgence of life from
inanimate ashes may be involved. Kerényi points to a symbolic cluster of images surrounding
birth in death, birth in fire, the ashes of the cremated votaries — all linked to the hope of life
after death.
26
Persephone herself was looked upon as the goddess of fire, for “through her
power the evil element was transformed into a kindly one.”
27
Perhaps also the ashes
symbolized the immortality which Demeter wished to bestow on the little prince Demophoön,
who was able to thrive and grow without food as long as she secretly placed him each night in
the fire like a log. When Demophoön’s mother, Metaneira, observes Demeter’s strange actionMixing the Kykeon
15
and protests it, Demeter takes the boy from the fire — but now he is doomed with the rest of
mankind to death. “Unknowing are ye mortals and thoughtless: ye know not whether good or
evil approaches.”
28
An augmenting motive to any of the preceding is simply the reverence
naturally felt towards the ashes remaining after a whole-burnt offering to the gods on a sacred
altar. These are not ashes to be simply disposed of as one would ordinary hearth ashes; they
partake of the sacral nature of the offering, and it is natural to attempt to incorporate them in
some further sacral function. The same instinct can be seen at work in the custom, observed to
this day in the Roman Catholic tradition, of reserving the ashes of the palms blessed on Palm
Sunday to be used on Ash Wednesday of the following liturgical season.
Would a potion containing enough ashes to hydrolyze ergot alkaloids be too basic and
caustic to drink? We suggest several possibilities: most simply, a solution of potassium
carbonate, if allowed to stand exposed to the air for a few days, would absorb enough carbon
dioxide from the air to be turned into the relatively harmless potassium bicarbonate.
Alternatively, as we have suggested earlier, a final addition of wine to the kykeon would
neutralize the ashes, and this seems reasonable since in Homer the kykeon always contains
wine. But in the Eleusinian myth, Demeter pointedly refuses to accept any wine to assuage
her grief, since it would be “contrary to themis,” against nature. This is thought to be more
than just an expression of her unwillingness to drink a beverage of joy while still in grief for
her daughter; rather, she declines because wine comes from Dionysus, and the rape of
Demeter’s daughter occurred on the Nysan Plain, where the Dionysian ground opened.
29
Indeed, the kykeon is possibly the Eleusinian drink in part because it stood as an alternative in
opposition to Dionysian wine. A third possibility, then, is that the final mixture was
neutralized (more effectively in any case since it is more acidic) by the addition of vinegar,
which as spoiled wine, might not offend Demeter and/or might even be symbolic of
participation in her grief.
We've had a little misunderstanding here.