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Lysergamides

Original Wikipedia articleen.wikipedia.org/wiki/Lysergamides revision used (24 October 2026)

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Overview

Lysergamides or ergoamides are amides of lysergic acid.[1] PW

Lysergamides, also known as ergoamides or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system.[2–6] WP

The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline. Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with addition of a small peptide moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include lisuride, terguride, bromerguride, and JRT.[7–19] WP

Lysergamides were first discovered and described in the 1930s.[20][21][22] WP

Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), UCD0120, and N-DEAOP-NMT, are also known.[23][24][25] WP

Drugs in this class on intoxicant.wiki

Every page on this site that a cited source puts in this class: 21 pages. A drug is listed when PsychonautWiki's "Lysergamides" page, revision 164957 lists it, or when its own PsychonautWiki, TripSit or Wikipedia entry names this class. Each name opens our page for that drug; long chemical names are shown by a shorter name the drug is also known by (hover for the full name).

Tags show who puts each drug in this class (hover for the exact wording): PW list = listed on PsychonautWiki's page for this class; PW = the drug's PsychonautWiki entry; TS = the drug's TripSit entry (drug category); WP = the drug infobox of the drug's Wikipedia article. These are classifications only, not dosage guidance.

References

  1. Other Jamieson CS, Misa J, Tang Y, Billingsley JM (2021-04-29). "Biosynthesis and synthetic biology of psychoactive natural products". Chemical Society Reviews. 50 (12): 6950–7008. DOI: 10.1039/D1CS00065A. ISSN 0306-0012. PMC 8217322. PMID 33908526. “There are three main ergot alkaloid classes, clavines, ergoamides (lysergamides), and ergopeptides, with 3 belonging to the ergoamide class.” 2.5 Lysergic acid and LSD, p. 6970
  2. Journal / agency Jamieson, Cooper S.; Misa, Joshua; Tang, Yi; Billingsley, John M. Biosynthesis and synthetic biology of psychoactive natural products. Chemical Society Reviews. doi:10.1039/D1CS00065A · PMID 33908526 · PMC8217322
  3. Journal / agency Wong, Garrett; Lim, Li Rong; Tan, Yong Quan; Go, Maybelle Kho; Bell, David J.; Freemont, Paul S.; Yew, Wen Shan. Reconstituting the complete biosynthesis of D-lysergic acid in yeast. Nature Communications. 2022-02-07. doi:10.1038/s41467-022-28386-6 · PMID 35132076 · PMC8821704
  4. Other St. Germaine, Danielle. Psychedelic Therapies Webinar Highlights. 2023-12-14
  5. Journal / agency Uhlig, Silvio; Rangel-Huerta, Oscar Daniel; Divon, Hege H.; Rolén, Elin; Pauchon, Kari; Sumarah, Mark W.; Vrålstad, Trude; Renaud, Justin B. Unraveling the Ergot Alkaloid and Indole Diterpenoid Metabolome in the Claviceps purpurea Species Complex Using LC–HRMS/MS Diagnostic Fragmentation Filtering. Journal of Agricultural and Food Chemistry. 2021-06-30. doi:10.1021/acs.jafc.1c01973
  6. Journal / agency Lee, K.; Poudel, Y. B.; Glinkerman, C. M.; Boger, D. L. Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs. Tetrahedron. 2015. doi:10.1016/j.tet.2015.05.093 · PMID 26273113 · PMC4528678
  7. Other Lysergic Acid Amides
  8. Journal / agency Hoffman AJ, Nichols DE. Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. Journal of Medicinal Chemistry. September 1985. doi:10.1021/jm00147a022 · PMID 4032428
  9. Journal / agency Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE. Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives. Pharmacology, Biochemistry, and Behavior. March 1994. doi:10.1016/0091-3057(94)90172-4 · PMID 8208787
  10. Journal / agency Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB. LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors. Psychopharmacology. April 1995. doi:10.1007/BF02245940 · PMID 7568626
  11. Journal / agency Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM. Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD). Journal of Medicinal Chemistry. September 2002. doi:10.1021/jm020153s · PMID 12213075
  12. Journal / agency Schiff PL. Ergot and its alkaloids. American Journal of Pharmaceutical Education. October 2006. doi:10.5688/aj700598 · PMID 17149427 · PMC1637017
  13. Journal / agency Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A. The pharmacology of lysergic acid diethylamide: a review. CNS Neuroscience & Therapeutics. 2008. doi:10.1111/j.1755-5949.2008.00059.x · PMID 19040555 · PMC6494066
  14. Journal / agency Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL. Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD). Drug Testing and Analysis. September 2016. doi:10.1002/dta.1884 · PMID 26456305 · PMC4829483
  15. Journal / agency Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL. Return of the lysergamides. Part II: Analytical and behavioural characterization of N⁶ -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ). Drug Testing and Analysis. January 2017. doi:10.1002/dta.1985 · PMID 27265891 · PMC5411264
  16. Journal / agency Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, Nichols DE, Halberstadt AL. Return of the lysergamides. Part III: Analytical characterization of N⁶ -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD). Drug Testing and Analysis. October 2017. doi:10.1002/dta.2196 · PMID 28342178 · PMC6230477
  17. Journal / agency Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL. Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775). Drug Testing and Analysis. February 2018. doi:10.1002/dta.2222 · PMID 28585392 · PMC6230476
  18. Journal / agency Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Wallach J, Halberstadt AL. Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD). Drug Testing and Analysis. August 2019. doi:10.1002/dta.2613 · PMID 31083768 · PMC6899222
  19. Journal / agency Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD. Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA). Psychopharmacology. February 2019. doi:10.1007/s00213-018-5055-9 · PMID 30298278 · PMC6848745
  20. Other Brimblecombe RW, Pinder RM. Hallucinogenic Agents. 1975
  21. Other Ravina E. The evolution of drug discovery: from traditional medicines to modern drugs. 2011
  22. Journal / agency Smith S, Timmis GM. 98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine. Journal of the Chemical Society (Resumed). 1932. doi:10.1039/jr9320000763
  23. Journal / agency Shulgin, Alexander T. Psychopharmacological Agents: Use, Misuse and Abuse. 1976. doi:10.1016/b978-0-12-290559-9.50011-9
  24. Other Nichols DE. Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid. May 1973
  25. Journal / agency Campaigne E, Knapp DR. Structural analogs of lysergic acid. J Pharm Sci. June 1971. doi:10.1002/jps.2600600602 · PMID 4942861

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