• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio | someguyontheinternet

More on D-lysergic acid hydroxyethylamide

Morninggloryseed

Morninggloryseed

Bluelight Crew
Joined
Aug 22, 2000
Messages
13,772
Location
Semi Retired
So I am finding literally dozens of papers on the biosynthesis of various lysergamides, including my favorite one, alpha-hydroxyethyl-d-lysergamide (d-lysergic acid hydroxyethylamine, LAH). A trend I see is this alkaloid is that LAH is usually the primary amide formed by C. Paspali, and ergine are secondary alkaloids formed, or are usually the produce of degradation of LAH. This is a neat thing for me to discover, because it would offer some reason why older morning glory and baby woodrose seeds seem to be much less psychedelic, and more narcotic in action.

One thing I can seemingly not find is any papers on the biosynthesis of ergolines in the various morning glory species.

Does anyone know of any, or even have a paper handy?

Also, I am going to specifically request a few papers as I do not have university access at this time….

(1) New aspects of submerged fermentation of Claviceps paspali. Bumbova-Linhartova, Renata; Flieger, Miroslav; Sedmera, Petr; Zima, Jiri. Inst. Microbiol., Czech. Acad. Sci., Prague, Czech. Applied Microbiology and Biotechnology (1991), 34(6), 703-6. CODEN: AMBIDG ISSN: 0175-7598. Journal written in English. CAN 114:225434 AN 1991:225434

(2) Separation of four isomers of lysergic acid -hydroxyethylamide by liquid chromatography and their spectroscopic identification. Flieger, M.; Sedmera, P.; Vokoun, J.; Ricicova, A.; Rehacek, Z. Inst. Microbiol., Czech. Acad. Sci., Prague, Czech. Journal of Chromatography (1982), 236(2), 453-9. CODEN: JOCRAM ISSN: 0021-9673. Journal written in English. CAN 97:68737 AN 1982:468737 CAPLUS

(3) Ergot alkaloids. IV. Biosynthesis of lysergie acid amides. Kleinerova, E.; Kybal, J. Res. Inst. Antibiot. Biotransform., Roztoky/Prague, Czech. Folia Microbiologica (Prague, Czech Republic) (1973), 18(5), 390-2. CODEN: FOMIAZ ISSN: 0015-5632. Journal written in English. CAN 79:124641 AN 1973:524641 CAPLUS



These three are very important to me, as I wish to better understand the stereochemistry of LAH. Getting them would be like a holy grail to me, as it would probably answer all of my questions as far as which isomer is likely to be in the plants

And last, can anyone produce

(1) Identification of ergoline alkaloids in the genus Argyreia and related genera and their chemotaxonomic implications in the Convolvulaceae. Chao, Jew-Ming; DerMarderosian, Ara H. Philadelphia Coll. Pharm. Sci., Philadelphia, PA, USA. Phytochemistry (Elsevier) (1973), 12(10), 2435-40. CODEN: PYTCAS ISSN: 0031-9422. Journal written in English. CAN 79:144182 AN 1973:544182 CAPLUS (Copyright 2005 ACS on SciFinder (R))

(2) Ergoline alkaloidal constituents of Hawaiian baby wood rose, Argyreia nervosa. Chao, Jew-Ming; Der Marderosian, Ara H. Philadelphia Coll. Pharm. Sci., Philadelphia, PA, USA. Journal of Pharmaceutical Sciences (1973), 62(4), 588-91. CODEN: JPMSAE ISSN: 0022-3549. Journal written in English. CAN 78:156668 AN 1973:156668 CAPLUS (Copyright 2005 ACS on SciFinder (R))
Biosynthesis of lysergic acid alpha-hydroxyethylamide. I. Natural selection of Claviceps paspali Stev and Hall. Yue D C; Yang Y P; Huo Z M; Yang Y C; He L Y Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae (1983 Aug), 5(4), 259-61. Journal code: 8006230. ISSN:1000-503X. Journal; Article; (JOURNAL ARTICLE) written in Chinese. PubMed ID 6228324 AN 84082366




I have had a number of very, very good psychedelic trips on morning glory and baby woodrose and intuition tells me LAH is responsible for a large part. The fact that C. Paspali is so easy to grow, and some strains only seem to produce the psychedelic ergolines, means that this fungus may be something very special.

Any help is so appreciated.
 
Every paper you mention is pretty old. Therefore someone would have to copy them from a journal and mail/fax them to you. I have access to a few. PM me if you are unable to obtain them.
 
You are awsome. Have you ever done any analysis on Stipa robusta?

The only bioassey I know of (besides myself) is that of J. Dekorne who claims 11 of the tiny seeds is a fully effective dosage.

Over the years I've collected a number of different authenticated specimens of Stip robusta, and none of them have any activity at this level. Two were obtained from very reliable wild-plant suppliers. These guys specialize in supplying wild plant specimens. They were not entheogen vendors. And the other was from a very reliable entheogenic plant supplier and I fully trust that what I got was what is represented.

Never tried any kind of personal bioassay of the grass itself. But the seeds are inactive at the levels I have tried.
 
Apparently N-(1-hydroxyethyl)lysergamide is an adduct compound formed from lysergamide (lysergic acid amide, LSA/LAA, LA-111) and acetaldehyde. This hints towards the idea that isn't the most stable of compounds, but would be pretty easily formed by the combination of lysergamide & acetaldehyde under physiological conditions (ie a way to get much more & better psychedelic activity from any lysergamide extracted from seed sources)
 
I (of course) am not asking for a 'recipe' which would violate the rules. And I understand that you are hinting at the addition of acetaldehyde to to a lysergamide-enriched solution may result in more LAOH. However, I am not sure what you mean by 'under physiological conditions.'
 
^ Meaning you don't have to reflux them together for hours to get the product. You just mix them together at normal physilogical temp, pH etc & voila, you get an equilibruim set up between it and lysergamide/acetaldehyde. If you can preceiptate it from soln while leaving the lysergamide in soln it could be almost a quantitative production

(the original info is in TIHKAL about p320 - the chapter on ergolines)
 
would it as safe to do a simple extraction of c.paspali to get something similr in fx to hbwr/morningglory...
 
would taking a vasodilator like yohimbine counteract the ergotism effects
 
^ Not enough, Yohimbine causes vaso-constriction in some parts of the body...
 
Sleepy Grass people! This grass usually comes infected with an ergot-like fungus....only this fungus ONLY produces lysergamides and none of the ergopeptide alkaloids.

I am the only person I know of who has performed a bioassay, but results were inconclusive. Who else wants to try!
 
What plant is C. Paspali?

Oh. A species of ergot. And supposedly this species only contains LAH, and none of the other alkaloids responsible for severe vascoconstriction, gangrene and other side effects? Thats interesting. Does it only grow on sleepy grass, or does it have no relation to sleepy grass and grow on grains like the other claviceps species?

Doesnt sleepy grass have some other alkaloids that cause severe nervous system depression and incoordination?
 
Last edited:
C Paspali preys on barley, and native species of grass. LAOH (aka LAH) is not the only alkaloid found in paspali...numerous other lysergamides and clavine alkaloids are also present. But none of the ergopeptide alkaloids (the bad ones) are present.

Sleepy grass (Stipa robusta) is afflicted by a different fungus, a grass endophyte in the acremonium family. From what I can tell, LA-111 is the primary alkaloid found but there is little out there related specifically to the fungus that hits sleepygrass. Ergoline producing species of acremonium also afflict fescue species. They are quite wide-spread.

I don't know how closely they are related to ergot.

Hey check this out.

http://www.pubmedcentral.gov/articlerender.fcgi?artid=1151833#figures-tables-sec

A fungus that makes people very sick every year makes a high amount of ergot alkaloids. Seems so far, all I can find is that they produce clavine alkaloids, not lysergamides. But clavine alkaloids may be psychoactive too.

Of course, you wouldn't want to take Aspergillus in any form, as people do die from it.
 
Last edited:
That would be very interesting if the certain strains of C. Paspali that contained only the pscyhedelic and not the ergotism causing alkaloids could be isolated and cultured.

I suppose the effects of LAOH are similar to LSA's contained in the creeping vines. Do you have further information on the effects?
 
That has already been done. Do a google search for C. Paspali and you will see dozens and dozens of citations on strains bred for specific alkaloids.
 
Is it C paspali that was used to produce LSD in a submerged culture where the medium had been made up with some unnatural amino acids replacing ones that would normally be present? In light of the above, it seems a far better candidate than C. purpurea
 
morninggloryseed said:
That has already been done. Do a google search for C. Paspali and you will see dozens and dozens of citations on strains bred for specific alkaloids.
Click to expand...

Has anyone experimented with these strains for use as a viable psychedelic drug?
 
apparently adding peppermint oil to mg seeds gives you d-lysergic acid hydroxyethylamide. is this true? theres a couple threads over in the shroomery about it...

f&b tell me more about the submerged culture of the c paspali. did they really get something to grow acid?
 
Last edited:
You must log in or register to reply here.
Top