Lysergic acid hydroxyethylamide

LSH
Clinical data
Other namesLAH; LSH; Lysergic acid N-(α-hydroxyethyl)amide; ᴅ-Lysergic acid methyl carbinolamide; N-(1-Hydroxyethyl)lysergamide; N(HOE)-LA; Lysergic acid-α-hydroxyethylamide
Legal status
Legal status
  • Illegal in France[1]
Identifiers
IUPAC name
  • 9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.020.079
Chemical and physical data
FormulaC18H21N3O2
Molar mass311.385 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@H](NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C)O
InChI
  • InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23)/t10-,12+,16+/m0/s1 N
  • Key:WYTJZJPVCDWOOI-KANYHAFZSA-N N
 NY (what is this?)  (verify)

Lysergic acid hydroxyethylamide (LSH or LAH), also known as lysergic acid N-(α-hydroxyethyl)amide, is an ergoamide and an ergoline. It is perhaps the main constituent of the parasitic fungus, Claviceps paspali;[2][3][4] and found in trace amounts in Claviceps purpurea.[5][6] C. paspali and C. purpurea are ergot-spreading fungi. Periglandula, Clavicipitacepus fungi, are permanently symbiotically connected to an estimated 450 species of Convolvulaceae[7] and thus generate LAH in some of them (42 generate ergolines, by Eckart Eich's review[8]). The most well-known ones are Ipomoea tricolor (“morning glory”), Turbina corymbosa (coaxihuitl), and Argyreia nervosa (Hawaiian baby woodrose). LAH is structurally similar to ergonovine, which is also known as lysergic acid hydroxymethylethylamide.

The more well-known analog, lysergic acid amide (syn. ergine), is more prominent in analytical results because LAH easily decomposes to ergine.[9][10] Ergine is only present because of the decomposition of LAH (and lysergic acid hydroxymethylethylamide and ergopeptines or their ergopeptam precursors); it is not generated.[11][12][13][14][15] Indeed, a 2016 analysis found that fresher I. tricolor seeds contained more LAH than the other two batches analyzed[16] (another interesting finding is that penniclavine was the predominant ergoline.)

  1. ^ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  2. ^ Arcamone F, Bonino C, Chain EB, Ferretti A, Pennella P, Tonolo A, Vero L (July 1960). "Production of lysergic acid derivatives by a strain of Claviceps paspali Stevens and Hall in submerged culture". Nature. 187 (4733): 238–239. Bibcode:1960Natur.187..238A. doi:10.1038/187238a0. PMID 13794048.
  3. ^ Castagnoli N, Corbett K, Chain EB, Thomas R (April 1970). "Biosynthesis of N-(alpha-hydroxyethyl) lysergamide, a metabolite of Claviceps paspali Stevens and Hall". The Biochemical Journal. 117 (3) (published 1970-04-01): 451–455. doi:10.1042/bj1170451. PMC 1178946. PMID 5419742.
  4. ^ Basmadjian G, Floss HG, Gröger D, Erge D (1969). "Biosynthesis of ergot alkaloids. Lysergylalanine as precursor of amide-type alkaloids". J. Chem. Soc. D (8): 418–419. doi:10.1039/C29690000418. ISSN 0577-6171.
  5. ^ Schultes R (1973). "4. Plants of Hallucinogenic Use / The Fungi". The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. p. 37. ISBN 9780398064167.
    "Whereas ergine, lysergic acid hydroxyethylamide, and lysergyl L-valine methylester occur in ergot of rye only in trace amounts, ergonovine (synonyms ergometrine, ergobasin), which is the specific oxytocic factor of a ergot, is often found in remarkable quantities. In contrast, ergine and hydroxyethylamide of lysergic acid are the main constituents of certain ergot growing on wild grasses, e.g. Paspalum distichum." 4. Plants of Hallucinogenic Use / The Fungi, p. 37
  6. ^ Wasson RG, Hofmann A, Ruck CA, Webster P (November 25, 2008) [1978]. Forte R (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.
    "We analyzed ergot of wheat and ergot of barley in our laboratory and they were found to contain basically the same alkaloids as ergot of rye, viz. alkaloids of the ergotamine and ergotoxine group, ergonovine, and sometimes also traces of lysergic acid amide. As I said before, ergonovine and lysergic acid amide, both psychoactive, are soluble in water whereas the other alkaloids are not." Albert Hofmann, 2. A Challenging Question and my Answer, p. 42
  7. ^ Leistner E, Steiner U (February 3, 2018). "The Genus Periglandula and Its Symbiotum with Morning Glory Plants (Convolvulaceae)". In Anke T, Schüffler A (eds.). Physiology and Genetics. Cham: Springer International Publishing. pp. 131–147. doi:10.1007/978-3-319-71740-1_5. ISBN 978-3-319-71739-5. Retrieved 2024-11-21.
  8. ^ Eich E (January 12, 2008). "4.2 Ergolines". Solanaceae and convolvulaceae - secondary metabolites: biosynthesis, chemotaxonomy, biological and economic significance: a handbook. Berlin, Heidelberg: Springer-Verlag. doi:10.1007/978-3-540-74541-9. ISBN 978-3-540-74540-2. OCLC 195613136
    Table 4.1 Unambiguously ergoline-positive Ipomoea species (pages 225-227)
    Table 4.4 Unambiguously ergoline-positive Argyreia species (p. 236)
    Table 4.5 Unambiguously ergoline-positive Stictocardia and Turbina species (p. 238)    {{cite book}}: CS1 maint: postscript (link)
  9. ^ Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. p. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. "These compounds, although well documented as components in the Convolvulaceae, are possibly lost in several of the analyses of alkaloid composition. They are extremely unstable, and are very readily degraded into acetaldehyde and the corresponding amide, ergine or isoergine." (p. 72) [...] "Lysergic acid hydroxyethylamide appears, in uterus response studies of the guinea pig and rabbit (Glasser, 1961), to be about half as potent as its homolog ergometrine, and in mice and rabbits it shows a sympathomimetic response very similar to that described for ergine. This is indicative of potential LSD-like activity."
  10. ^ Schultes RE, Hofmann A (1973). The Botany and Chemistry of Hallucinogens. Springfield, IL: Charles Thomas. p. 246. ISBN 9780398064167.
    "Later, it was found that ergine and isoergine were present in the seeds to some extent in the form of lysergic acid N-(1-hydroxyethyl) amide and isolysergic acid N-(1-hydroxyethyl) amide, respectively, and that, during the isolation procedure, they easily hydrolize to ergine and isoergine, respectively, and acetaldehyde." 4. Plants of Hallucinogenic Use / Convolvulaceae, p. 246
  11. ^ Flieger M, Sedmera P, Vokoun J, R̆ic̄icovā A, R̆ehác̆ek Z (1982-02-19). "Separation of four isomers of lysergic acid α-hydroxyethylamide by liquid chromatography and their spectroscopic identification". Journal of Chromatography A. 236 (2): 441–452. doi:10.1016/S0021-9673(00)84895-5. ISSN 0021-9673.
  12. ^ Ramstad E (1968). "Chemistry of alkaloid formation in ergot". Lloydia. 31: 327–341.
  13. ^ Kleinerová E, Kybal J (September 1973). "Ergot alkaloids. IV. Contribution to the biosynthesis of lysergic acid amides". Folia Microbiologica. 18 (5): 390–392. doi:10.1007/BF02875934. PMID 4757982.
  14. ^ Panaccione DG, Tapper BA, Lane GA, Davies E, Fraser K (October 2003). "Biochemical outcome of blocking the ergot alkaloid pathway of a grass endophyte". Journal of Agricultural and Food Chemistry. 51 (22): 6429–6437. doi:10.1021/jf0346859. PMID 14558758.
  15. ^ Panaccione DG (2010). "Ergot alkaloids". In Hofrichter M (ed.). The Mycota, Industrial Applications. Vol. 10 (2nd ed.). Berlin-Heidelberg, Germany: Springer-Verlag. pp. 195–214.
  16. ^ Nowak J, Woźniakiewicz M, Klepacki P, Sowa A, Kościelniak P (May 2016). "Identification and determination of ergot alkaloids in Morning Glory cultivars". Analytical and Bioanalytical Chemistry. 408 (12) (published February 14, 2016): 3093–3102. doi:10.1007/s00216-016-9322-5. PMC 4830885. PMID 26873205.
    "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." (Analysis of different Ipomoea seeds)
    See Table 3 under "Analysis of different Ipomoea seeds".
    Concentration values for "LSH", "Lyzergol/isobars", penniclavine, and chanoclavine can be obtained by dividing the concentration values of ergine or ergometrine by their relative abundance values and multiplying that number by the relative abundance value of the specified chemical.
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