NOTE: Pregnant Women must NEVER use any morning glory, Hawaiian Woodrose or ergot sourced products or preparations. Besides some compounds being very toxic to the liver and kidneys, many of these substances can also cause uteral contractions. There are other contraindications you should be aware of if you're new to the idea of eating these seeds or preparing an extract.
Stomach discomfort with morning glory is common. Many years ago, it was common for the seeds to be coated with strychnine to prevent rats from eating them. A good scrubbing with a brush was supposed to fix that, but one night in a fit of wild abandon, we hastily prepared 14 pkts of seeds between 2 of us by quickly scrubbing them in water. It didn't work and we both got mild (which is still VERY painful) strychnine poisoning. However, a search in attempt to explain the stomach upsets experienced with untainted seeds, reveals that strychnine and closely related chemicals are actually naturally present in the seeds themselves (although strychnine itself is listed only under "Sliver Morning Glory" or Woodrose).
Before that time, at ~ age 17, I once extracted the resins and alkaloids for the purpose of making a (then) legal drug for self administration. To be the only drug making I was ever was involved in, it was a simple exercise, although for some reason I could never remember the solvent I used for extracting other nasties (responsible for the tummy pain).
After reading the
FAQ from Erowid I decided it must have simply been water. It would explain a lot as I didn't have a great variety of solvents to choose from. I did keep good notes from that period (like any aspiring scientist) but I lost the lot (and many books) in a flood in 83 - a year after retrieving them from my mums garage
The procedure was to soak the seeds in Pet ether for a couple of hours, drain and keep the solvent, dry off and keep the goo. The seeds are dried and further soaked in Methanol for a week, shaking the jar each day. This is evaporated and the 2 extracts combined. The added extracts are then soaked in water overnight. The result was an ~ 1cm cube of gummy resin. It worked a treat and no stomach was noticed, although, a while later I was to try acid and found the trip to be quite different. After the seeds fiasco I could never be bothered again, and my stomach goes funny at the mere thought
There are several other alkaloids of interest in Morning Glory, explaining perhaps why the trip is considered so unique, although as Shulgin mentions, some are not thought to be contributing to the effects.
Although there are many other chemical treasures in the ergot fungal world, I would like to wrap this commentary up with a return to the topic of morning glory seeds. Four additional alkaloids of the ergot world must be acknowledged as being potentially participating factors in the MGS story. With each of these, the primary ergoline ring system is largely intact but the amide function is completely gone. The carboxyl group has been reduced to the alcohol to give elymoclavine. There is the related molecule present which is the isomer with the double bond moved to be conjugated with the aromatic ring; it is called lysergol. There is the same molecule but with a hydroxy group attached to the 8-position carbon atom (an ethyleneglycol!) ; it is called penniclavine. And lastly, that D-ring can actually be opened between the 5 and 6 positions, to give us a secondary amine tryptamine derivative, chanoclavine. To be completely anally retentive in this Ipomoea inventory, mention must be made of five alkaloids that are present in truly trace amounts, all of which have no oxygen atoms present whatsoever on that substitution on the ergoline 8-position. These are the 8-methyl isomers agroclavine, setoclavine, festuclavine and cycloclavine, and the methylene analogue lysergene. These structures in effect define absolute obscurity, and most probably do not contribute to the morning glory intoxication state. But the others, some present is sizable amounts, may someday help explain why the pharmacology of these seeds is so different than that of the major isolates, the ergines.
From
Tihkal 26 - Erowid
Here's a rather deep (chemistry) but excellent paper on the
Progress and Prospects of Ergot Alkaloid Research
Other refs:
Dr Dukes Phytochemical and Ethnobotanical Database:
Chemicals in: Ipomoea violacea L. (Convolvulaceae) -- Ololiuqui, Tlitlitzen
Chemicals in: Argyreia nervosa (BURM.) BOJER (Convolvulaceae) -- Silver Morning Glory, Wood Rose
