Semisynthetic ergoamides identified in a natural product for the first time:
“On the other hand, methylergometrine, methysergide, and lysergylalanine were detected, which have not yet been reported as compounds of
Argyreia nervosa seeds.”
Paulke, A., Kremer, C., Wunder, C., Wurglics, M., Schubert-Zsilavecz, M., & Toennes, S. W. (2015). Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Forensic science international, 249, 281–293. DOI: 10.1016/j.forsciint.2015.02.011. 3. Results and Discussion, p. 283
Methylergometrine is lysergic acid butanolamide and lysergic acid hydroxymethylpropylamide. It is a methylated analog of ergometrine (lysergic acid propanolamide/lysergic acid hydroxymethylethylamide/ergonovine), a subject of interest in The Road to Eleusis (Wasson, Hofmann, Ruck, 1978), in chapter 2 (written by Hofmann). Methylergometrine was created by Hofmann, like LSD. “I used the method developed for the synthesis of ergonovine for the preparation of many chemical modifications of ergonovine. One of these partly synthetic derivatives of ergonovine was lysergic acid butanolamide. This is used today in obstetrics, replacing to a major extent ergonovine, under the brand name ‘Methergine’ to stop postpartum haemorrhage.”[1] Hofmann includes a trip report for ergometrine[2] and Owsley even said that Hofmann told him that it is “nearly identical to LSD in effect”, although that's a questionable claim, especially since Owsley also describes ergot as having “many highly psychedelic alkaloids.”[3]
Several others have also tried ergometrine in “higher-than-therapeutic” doses and also reported a psychedelic high. I added these references to
Wikipedia (2nd par. under Pharmacology).
Some individuals also tried methylergometrine and published their comments in an article called ‘Entheogenic (Hallucinogenic) Effects of Methylergonovine’.[4]
Methysergide is methylated methylergometrine, i.e., methylmethylergometrine and lysergic acid hydroxymethylpropylmethylamide.
Lysergylalanine is a biosynthetic intermediate between the simpler ergoclavine alkaloids and the more complex ergoamides and ergopeptines. The study in question did not quantify their findings (e.g., mg per gm of seed material), but I suspect it was only found in trace amounts. I don’t know if it's an ergoamide.
There's also another trace ergoamide: 8-hydroxyergine.[5][6] So in total, assuming the above study is true, there are 6 natural ergoamides: ergine (“LSA”), 8-hydroxyergine, ergonovine, methylergonovine, methylmethylergonovine, and lysergic acid hydroxyethylamide.
1. Wasson, R. G.; Hofmann, Albert; Ruck, Carl A. P.; Webster, Peter (November 25, 2008). Forte, Robert (ed.). The Road to Eleusis: Unveiling the Secret of the Mysteries (30th Anniversary ed.). Berkeley, Calif.: North Atlantic Books. ISBN 978-1-55643-752-6.
https://books.google.com/books?id=7JC7EAAAQBAJ&pg=PA38 2. A Challenging Question and my Answer, p. 38
2. Same as above. “This was an experiment performed without attention to ‘set and setting’ but it proves that ergonovine possesses a psychotropic, mood-changing, slightly hallucinogenic activity when taken in the same amount [as an] effective dose of lysergic acid amide, the main constituent of ololiuhqui. Its potency is about one twentieth of the potency of LSD and about five times that of psilocybin.” p. 41
3. Bruce Eisner: Well, people could say the same thing about LSD, they could say there’s sassafras and there’s nutmeg in nature, and there is morning glories and ergot in nature, but you have to do the chemistry in order to make something that’s effective.
Owsley: No, that’s not true. Ergot contains many natural, highly psychedelic alkaloids. [Isoergine] is one of them; hydroxy-methyl-lysergamide is another one, and in fact, is considered nearly identical to LSD in effect. Albert [Hofmann] told me so himself. They believe that it was this derivative contained in extracts of [C. paspali] that was used in the [Eleusinian] Mysteries.
Interview with an Alchemist: Bear Owsley Interview. Bruce Eisner's Writings, Jan 10, 2004
4. Ott, J., & Neely, P. (1980). Entheogenic (Hallucinogenic) Effects of Methylergonovine. Journal of Psychedelic Drugs, 12(2), 165–166. DOI: 10.1080/02791072.1980.10471568
“Unlike LSD, however, both methylergonovine and ergonovine evoke lassitude and a dreamy semi-narcotic state, effects previously ascribed by Hofmann to d-lysergic acid amide (also known as ergine or LA-111), the active principle of the Mexican entheogenic drug
ololiuhqui (
Rivea [
Turbina]
corymbosa), also found in some strains of ergot (Hofmann 1964). In profound contrast to LSD, the somatic effects of methylergonovine and ergonovine overshadow the psychic effects, with uncomfortable somatic side effects likely to supervene at doses sufficient to elicit profound entheogenic effects. Accordingly, neither drug seems at all likely to displace LSD in the recreational drug scene.”
Further reading:
https://nervewing.blogspot.com/2020/06/obscure-and-unknown-ergometrine-and.html
5. Flieger, M.; Linhartová, R.; Sedmera, P.; Zima, J.; Sajdl, P.; Stuchlík, J.; Cvak, L. (September 1, 1989). New Alkaloids of Claviceps paspali. Journal of Natural Products. 52 (5): 1003–1007. doi:10.1021/np50065a014. ISSN 0163-3864.
6. Petroski, Richard J.; Powell, Richard G.; Clay, Keith (March/April 1992). Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte. Natural Toxins. 1 (2): 84–88. doi:10.1002/nt.2620010205. ISSN 1056-9014
“8-Hydroxylysergic acid amide was isolated with difficulty as it was present as only a minor alkaloid in endophyte-infected sleepygrass (0.3 pg/g dry wt).” Results and Discussion, p. 87
I've posted a lot of info about this subject in my Shroomery Journal:
https://www.shroomery.org/forums/postlist.php/Journal/240779