Talk:Ergine

Untitled

Article LSA listed on Wikipedia:Votes for deletion Apr 27 to May 3 2004, consensus was not reached. Discussion:

Page exists due to a persistent myth that LSA is the active hallucinogen in seeds of certain Convolvulaceae species. Actually the active agent of these seeds has not been determined, and it is probably not LSA, but one or more of the related ergolines (see that entry for discussion). Since the topic covers multiple chemicals and multiple plant species, it should live either in the chemical family entry (ergolines) or the plant family entry (Convolvulaceae). I opted for the former, made the page with general info including info on the hallucinogenic seeds, and ended up not copying over any text from the LSA entry because it is mostly not worth keeping. For example, sentence 1 is false (see ergoline). Sentence 3 talks about species of a species (???) and fails to note that Heavenly Blues etc are varieties of I. tricolor, or that many other species are known to contain ergolines. Sentence 4 is irrelavant and untrue (isolating it from all the other stuff is complicated). Sentence 5 is false. Sentence 6 is irrelevant and will potentially attract criticism of wikipedia for inciting illegal activities. That leaves sentence 2 which is neither here nor there after considering the fact that LSA is probably not of interest anyway. So I vote deleting all the text and replacing the page with a redirect to ergoline. -- Rkundalini 13:28, 27 Apr 2004 (UTC)

• Keep, with edits. Never heard of this before. Although, if what you say is true, thats no reason to delete an article on such a significant chemical as lysergic acid amide. If the myth is so persistent (as it is noted on the Lycaeum and Erowid both as LSA being the active psychoactive ingredient is Morning glory seeds), then people are going to come here and not ergolines for information. I propose not a redirect, but rather a massive rewrite of the article. With sources that back up your data. DryGrain 13:54, 27 Apr 2004 (UTC)
  • If LSA was a redirect to ergoline, that wouldn't be a problem. But still if you (& others?) think a page especially for LSA (in addition to the coverage it gets in ergoline, seeing it is one) is worth doing to dispel the misinformation, I can go with that. --Rkundalini 09:05, 29 Apr 2004 (UTC)

• You mean the morning glory thing is just a myth? Well, I've been had. Keep the page, though, since it is a real chemical. Right? By the way, I'd type in ololiuqui if I were searching for morning glory seeds. Don't tell me that's different from ergoline . . . or is it? Wiwaxia 04:32, 29 Apr 2004 (UTC)
  • It is a real chemical, but it is no more special (in fact, less special) than many of the other ergoline derivatives (of which it is a member) that are covered under ergoline and do not need to command their own page. Re "I've been had" maybe I've not been clear enough... the seeds are indeed hallucinogenic, they do indeed contain LSA, but LSA is seemingly not hallucinogenic, so one or more of the many other ergoline derivatives present is likely responsible for the hallucinogenic effect. Do I need to make this issue a bit clearer in the ergoline entry? -- Rkundalini 09:05, 29 Apr 2004 (UTC)
    • So LSA is in the morning glory seeds after all? Oh, you should definitely clarify this in the article. Looks like the "correlation implies causation" attitude has been active in this myth. If you write that in, people will understand EXACTLY whether the myth is true and what the actual circumstances are. Wiwaxia 12:01, 29 Apr 2004 (UTC)

• Since the voting period has elapsed without much interest, I'll go with DryGrain's suggestion. Rkundalini 11:47, 3 May 2004 (UTC)

End discussion

VasoConstricion

Meaning the constriction of veins. I read somewhere that ergine can cause this, mkaing your balls turn brown, and your lips turn blue. Anyone can confirm this? —Preceding unsigned comment added by 86.83.121.172 (talk) 13:16, 12 November 2007 (UTC)

Page Moved

I moved the page to ergine, since this is the name most frequently used in literature. I could be wrong but I think the term LSA was cooked up somewhere along the line in internet / amateur literature since it sounds like "LSD". The name used by Sandoz (who named LSD) was LA-111, not LAA. The name ergine was switched to when it was first found in nature. Rkundalini 12:12, 4 May 2004 (UTC)

Yes! All instances of "LSA" should be removed from the article. — Preceding unsigned comment added by 96.232.159.249 (talk) 13:29, 26 November 2012 (UTC)

A myth? Please!

I suggest you read "Practical LSD Manufacture" by Uncle Fester. Also, take a look in the Erowid Vaults under LSA. I believe that it would be impossible for it to be a myth, since crystalline LSA can be (and has been) obtained from said seeds, and used for hallucinogenic purposes. If it were really another chemical (What's your mystery chemical?), it surely would have been discovered. All of the scientific information says that LSA is a hallucinogen, refer to "Psychedelic Chemistry, Third Expanded Edition" by Peter Stafford. If you still have your doubts, I suggest you follow simple extraction methods (tried and true) to get crystalline LSA, and dose yourself.

(Above stuff apparently by "Ddhix 2002")

• Regarding your statement that ergine can and has been obtained from the seeds and used for hallucinogenic purposes, and your suggestion that I (break the law and) follow simple extraction methods to get crystalline LSA, and dose myself: both of these statements are perfect illustrations of the correlation implies causation logical fallacy pointed out by Wiwaxia above. Yes, an alkaloid extract of the seeds will be predominantly composed of ergine, yes the extract will be impressively psychedelic. This does not imply that ergine is impressively psychedelic. The fact that numerous articles, especially ones on the web (e.g. the ones in the Erowid LSA vault), say that this is true, does not make it true. Only human trials of doses of pure ergine can prove or disprove the claim, and of all the trials I know of, which are all listed in part 2 of the article Mixing the kykeon are pretty unimpressive and tend to indicate that strong somatic and soporific effects are accompanied by at best a weak psychedelic action. Unless those books provide any information on further human trials of pure ergine, they have nothing to say about the matter. If they do, could you provide us with an excerpt? The idea that ergine isn't necessarily the active agent is not some thing I have made up myself. If you need to hear it from some big names, check out chapter 17 and entry 26 of TiHKAL, and part 2 of the article Mixing the kykeon. Regarding your question of what is "my mystery chemical", it could be any of the quite a few other ergolines that have been found in the seeds in lesser amounts, or it could be a result of synergies between the various ergolines present. Or it could be, after all, that ergine really does produce impressive psychedelic effects and that the previous results were unrepresentative due to e.g. the individual response of the handful of people involved, or due to the clinical setting of the experiment (this is Peter Webster's opinion on the matter), but this is yet to be proven either way. Rkundalini 12:25, 11 May 2004 (UTC)

The Anarchist Cookbook is hardly a reputable source of information. In fact, most of the "recipes" it contains will cause severe injuries or death if attempted. This should not the primary reference for this article, and it probably shouldn't be used at all. -(User:Fuzzform - Not logged in)

Physical properties

While I am looking at the original article by Smith and Timmis from 1932, here's a few physical characteristics:

Ergine is sparingly soluble in methyl alcohol and is conveniently separated from more soluble impurities by this solvent. It crystallises in colourless prisms which decompose with frothing at about 135C; blackening with evolution of gas occurs at about 230C. The crystals contain one molecular proportion of methyl alcohol, which is retained with remarkable tenacity and is not completely removed by many hours' heating at 90C in a vacuum. Ergine is readily soluble in acetone, soluble in chloroform and ethyl acetate, sparingly soluble in methyl and ethyl alcohols, ether, benzene, and almost insoluble in light petroleum and water. It crystallises very readily from aqueuous acetone in long colourlesss plates which decompose with frothing at 115C and on further heating blacken and undergo further decomposition at about 230C. This form is a dihydrate which is stable in air but completely loses its water when kept over sulphuric acid in a vacuum desiccator.

Do what you want with it, quoting verbatim is probably a copyright violation (although, it's from year 1932 - I don't really know). Cubbi 21:53, 4 April 2007 (UTC)

Pictures?

Use these if you want: [1] [2] [3]

I hereby grant that I have taken these and that they are public domain. It's Ergine extracted from 100 seeds of [Argyreia nervosa]. For obvious reason I'm not interested in creating an account (would be a sockbaby anyway) here.

legal status

Ergine is a DEA schedule 3 drug in the United States. What does that mean? Widsith 10:31, 19 June 2007 (UTC)

legal status in other countries?

does it have any legal status in the UK, AUS, Canada? and is it illegal to possess the seeds containing Ergine? ~april 08 —Preceding unsigned comment added by 86.151.141.155 (talk) 14:09, 16 April 2008 (UTC)

• Where I live (Romania), if they sell it in head/smart shops, it IS (obviously) legal to possess. LSA is legal. 94.52.112.143 (talk) 21:07, 27 July 2009 (UTC)

Effect on Canines?

I was wondering if anyone knows the effects of LSA on dogs? MattTheMan (talk) 06:22, 20 May 2008 (UTC)

Not psychedelic?

Tell that to my freind who started feeding an imaginary horse. —Preceding unsigned comment added by 71.139.192.181 (talk) 06:26, 12 November 2008 (UTC)

You can get hallucinations just by wanting them. Drugs make that easier, that doesn't mean they are psychedelic —Preceding unsigned comment added by 83.134.190.88 (talk) 14:28, 7 September 2010 (UTC)

Morning glories are certainly psychedelic, ergine is not. C6541 (T↔C) 15:11, 15 June 2012 (UTC)

there is ergine in morning glories, so they are 2A02:F6E:4B03:0:A339:AD1F:BF6D:2E80 (talk) 19:02, 21 March 2023 (UTC)

Anarchist cookbook

Anarchist Cookbook is no more reliable than uncyclopedia. Please remove it as source, and find semi-serious sources like erowid. —Preceding unsigned comment added by 83.134.190.88 (talk) 14:27, 7 September 2010 (UTC)

Routes: Oral, Intramuscular

It's silly that these two routes of administration are speciffically indicated based on what has been uncovered in the literature. This implys that ergine cannot be injected intravenously, for example, as with codeine, which causes pulmonary edema. Just because you didn't find literature where it was given intravenously, doesn't mean you go and make a fancy profile that says "oral, intramuscular." classic example of Wikipedia being overly technical and overly encompassing. — Preceding unsigned comment added by 96.232.159.249 (talk) 13:34, 26 November 2012 (UTC)

Does anyone have a copy of the Subproject 22 document?

What the title says. — Preceding unsigned comment added by PA292 (talk • contribs) 21:24, 12 February 2013 (UTC)

Ergine receptor affinities!

https://www.ncbi.nlm.nih.gov/pubmed/23665164

"

Abstract

ETHNOPHARMACOLOGICAL RELEVANCE:

The convolvulacea Argyreia nervosa (Burm. f.) is well known as an important medical plant in the traditional Ayurvedic system of medicine and it is used in numerous diseases (e.g. nervousness, bronchitis, tuberculosis, arthritis, and diabetes). Additionally, in the Indian state of Assam and in other regions Argyreia nervosa is part of the traditional tribal medicine (e.g. the Santali people, the Lodhas, and others). In the western hemisphere, Argyreia nervosa has been brought in attention as so called "legal high". In this context, the seeds are used as source of the psychoactive ergotalkaloid lysergic acid amide (LSA), which is considered as the main active ingredient.

AIM OF THE STUDY:

As the chemical structure of LSA is very similar to that of lysergic acid diethylamide (LSD), the seeds of Argyreia nervosa (Burm. f.) are often considered as natural substitute of LSD. In the present study, LSA and LSD have been compared concerning their potential pharmacological profiles based on the receptor binding affinities since our recent human study with four volunteers on p.o. application of Argyreia nervosa seeds has led to some ambiguous effects.

MATERIAL AND METHODS:

In an initial step computer-aided in silico prediction models on receptor binding were employed to screen for serotonin, norepinephrine, dopamine, muscarine, and histamine receptor subtypes as potential targets for LSA. In addition, this screening was extended to accompany ergotalkaloids of Argyreia nervosa (Burm. f.). In a verification step, selected LSA screening results were confirmed by in vitro binding assays with some extensions to LSD.

RESULTS:

In the in silico model LSA exhibited the highest affinity with a pKi of about 8.0 at α1A, and α1B. Clear affinity with pKi>7 was predicted for 5-HT1A, 5-HT1B, 5-HT1D, 5-HT6, 5-HT7, and D2. From these receptors the 5-HT1D subtype exhibited the highest pKi with 7.98 in the prediction model. From the other ergotalkaloids, agroclavine and festuclavine also seemed to be highly affine to the 5-HT1D-receptor with pKi>8. In general, the ergotalkaloids of Argyreia nervosa seem to prefer serotonin and dopamine receptors (pKi>7). However, with exception of ergometrine/ergometrinine only for 5-HT3A, and histamine H2 and H4 no affinities were predicted. Compared to LSD, LSA exhibited lower binding affinities in the in vitro binding assays for all tested receptor subtypes. However, with a pKi of 7.99, 7.56, and 7.21 a clear affinity for 5-HT1A, 5-HT2, and α2 could be demonstrated. For DA receptor subtypes and the α1-receptor the pKi ranged from 6.05 to 6.85.

CONCLUSION:

Since the psychedelic activity of LSA in the recent human study was weak and although LSA from Argyreia nervosa is often considered as natural exchange for LSD, LSA should not be regarded as LSD-like psychedelic drug. However, vegetative side effects and psychotropic effects may be triggered by serotonin or dopamine receptor subtypes.

"

Iownutopia 10:33, 13 June 2017 (UTC)  — Preceding unsigned comment added by Iownutopia (talk • contribs)  

"First description"

How could someone writing the "first description" of ergine preparation in 1941 describe its use back to Aztec times? Wouldn't that require drawing on older written sources? 73.71.251.64 (talk) 07:00, 3 November 2019 (UTC)

Peter Webster's equilibrium hypothesis

Peter Webster is the founder of psychedelic-library.org. In 2006 he gave a lecture about the Kykeon and ergine at the 2006 LSD symposium. Motivated by a powerful experience with chemically refined morning glory seeds, little interest in ergine in the psychedelic community, and his knowledge of chemistry, Webster formulated a hypothesis that a certain form of ergine has a more LSD-like effect than others.

“So, we have the possibility that a molecule of ergine can be in one of three different states: It can be ergine in the chair or boat conformation, or it can be isoergine in the chair conformation. And in many chemical and physical situations, the three forms are constantly converting from one form to the others, and achieving a typical equilibrium distribution.” (1:06:35)

Webster had also dismissed ergonovine (lysergic acid hydroxymethylethylamide), for an undisclosed reason, and lysergic acid hydroxyethylamide, as contributors.

The hydroxyethylamide long thought to be psychoactive actually can never reach the brain, since this compound is a labile adduct of ergine and acetaldehyde. It is therefore transformed into ergine and isoergine rapidly, even by mild extraction methods.

vbest regards, peter

Quoted by tregar, 9/4/06, https://drugs-forum.com/threads/lucid-visual-morning-glory-extract-theory.30919/#post-184703

I pointed out to Webster that Gröger 1963* identified lysergic acid hydroxyethylamide in a greater quantity than ergine and I asked him if it might metabolize into the hypothetical superior form. Webster again stated that he didnit think LAH could be effectively metabolized but that yes, it may play a role in formulating the superior equilibrium.

As implied in the article, LAH and ergonovine are generated by the fungi and ergine only results when they decompose. It's rumored that LAH decomposes quickly in seeds and that fresh seeds are key to getting LSD-like effects, and indeed, the results of a recent study on these seeds provides some support for that:

“As has been demonstrated in this study, LSH is a labile compound, and therefore the variances in its concentration may be due to different age and storage conditions of the seeds rather than difference in plant metabolism. Indeed, seeds IT-HB2, which express highest concentration of LSH, were bought directly from the producer, whereas seeds IP-HB1 were purchased in retail stores.”

Identification and determination of ergot alkaloids in Morning Glory cultivars. Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P. 2016. Anal Bioanal Chem. 408(12):3093-102. doi: 10.1007/s00216-016-9322-5 (Analysis of different Ipomoea seeds)

Webster also published two written works based on his lecture, specifically, (1) the chapter, Mixing the Kykeon Anew in Sacred Mushrooms of the Goddess**, and (2) the appendix, Kykeon Chemistry in the 30ᵗʰ anniv. edition of The Road to Eleusis.†

[*] Gröger D. (1963) Über das Vorkommen von Ergolinderivaten in Ipomoea-Arten. Flora 153:373–382. DOI: 10.1016/S0367-1615(17)33310-4

[**] Sacred Mushrooms of the Goddess: The Secrets of Eleusis. Carl A.P. Ruck (ed.). 2006. Berkeley, California: Ronin Publishing, Inc. ISBN 978-1-57951-030-5. https://books.google.com/books?id=XTzlCgAAQBAJ&pg=PA171

[†] The Road to Eleusis: Unveiling the Secret of the Mysteries (30th Anniversary ed.). Wasson RG, Hofmann A, Ruck CA, Webster P, Forte R (ed.). 2008 (1978). Berkeley, Calif.: North Atlantic Books. ISBN 978-1-55643-752-6. https://books.google.com/books?id=7JC7EAAAQBAJ&pg=pa154

Wk472 (talk) 02:56, 11 December 2024 (UTC)