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Ergine

Ergine
Clinical data
Other namesLysergic acid amide; LSA; LAA;[1][2][3][4][5] ᴅ-Lysergic acid amide; ᴅ-Lysergamide, d-Lysergamide; LA-111; "Lacy"; 6-Methyl-9,10-didehydroergoline-8β-carboxamide
Pregnancy
category
Routes of
administration		Oral, intramuscular injection, subcutaneous injection
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen; Sedative
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
MetabolismHepatic
Onset of action0.3–3 h (morn. glory seeds)[9][10]
Duration of action4–10 h (morn. glory seeds)[9][10]
ExcretionUrine[11]
Identifiers
  • (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.841 Edit this at Wikidata
Chemical and physical data
FormulaC16H17N3O
Molar mass267.332 g·mol−1
3D model (JSmol)
Melting point135 °C (275 °F) Decomposes[12]
  • O=C(N)[C@@H]1C=C2C3=CC=CC4=C3C(C[C@@]2([H])N(C1)C)=CN4
  • InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1 checkY
  • Key:GENAHGKEFJLNJB-QMTHXVAHSA-N checkY
  (verify)

Ergine, also known as lysergic acid amide (LSA or LAA) as well as LA-111, is a psychoactive compound of the ergoline and lysergamide families related to lysergic acid diethylamide (LSD).[10][13][9][14] It is an alkaloid and is found in certain plants such as morning glory seeds and in certain fungi such as Claviceps purpurea (ergot) and Periglandula species.[13] The latter fungi have a symbiotic relationship with morning glories and are the source of the ergine in their seeds.[13] Ergine is orally active and produces relatively mild hallucinogenic effects as well as pronounced sedative effects.[10][15][16][17][18][19][20]

The most common sources of ergine for use as a drug are the seeds of morning glory species including Ipomoea tricolor (tlitliltzin), Ipomoea corymbosa (ololiuhqui), and Argyreia nervosa (Hawaiian baby woodrose).[13][21][15][22] Morning glory seeds have a history of entheogenic use in Mesoamerica dating back at least hundreds of years.[13][17][23] They have also since been used by many Westerners.[24] In addition to ergine, morning glory seeds contain other ergolines such as lysergic acid hydroxyethylamide (LSH), lysergic acid propanolamide (ergonovine), and isoergine.[16][17][13] Some of these compounds are pharmacologically active and are thought to contribute to the effects of the seeds as well.[16][17][13][25][26] There has been debate about the role of ergine in causing the psychedelic effects of morning glory seeds.[15][27][28][19]

Ergine was first described by Sidney Smith and Geoffrey Timmis after they isolated it from ergot in 1932.[12] It was first synthesized subsequent to its isolation in the 1930s.[16][29] Albert Hofmann, the discoverer of LSD's psychedelic effects in 1943, evaluated the effects of ergine in humans in 1947 and described the results many years later.[15][16][26][30] He and his colleagues also isolated ergine from morning glory seeds in 1960.[31][32][16][13] Morning glory seeds started to become frequently used as a recreational drug that same year[24] and has been widely used since.[13][31][33][34] Recreational use of morning glory seeds may be increasing due to their inexpensiveness, widespread availability, and lack of legal restrictions.[10][31] Ergine has been encountered as a novel designer drug in Europe.[35] Ergine, though not morning glory seeds, has become a controlled substance in various places in the world.[36][37]

  1. ^ Oliver JW, Abney LK, Strickland JR, Linnabary RD (October 1993). "Vasoconstriction in bovine vasculature induced by the tall fescue alkaloid lysergamide". Journal of Animal Science. 71 (10): 2708–2713. doi:10.2527/1993.71102708x. PMID 7901191.
  2. ^ Genest K, Sahasrabudhe MR (1966). "Alkaloids and Lipids of Ipomoea, Rivea and Convolvulus and Their Application to Chemotaxonomy". Economic Botany. 20 (4): 416–428. Bibcode:1966EcBot..20..416G. doi:10.1007/BF02904064. ISSN 0013-0001. JSTOR 4252802.
  3. ^ Genest K (November 1966). "Changes in ergoline alkaloids in seeds during ontogeny of Ipomoea violacea". Journal of Pharmaceutical Sciences. 55 (11): 1284–1288. doi:10.1002/jps.2600551123. PMID 5969787.
  4. ^ Genest K (September 1965). "A direct densitometric method on thin-layer plates for the determination of lysergic acid amide, isolysergic acid amide and clavine alkaloids in morning glory seeds". Journal of Chromatography. 19 (3): 531–539. doi:10.1016/S0021-9673(01)99495-6. PMID 5864081.
  5. ^ Brown JK, Malone MH (1978-01-01). ""Legal highs"--constituents, activity, toxicology, and herbal folklore". Clinical Toxicology. 12 (1): 1–31. doi:10.3109/15563657809149579. PMID 343978.
  6. ^ "Erowid Morning Glory Basics". Erowid.org. Retrieved 2012-02-03.
  7. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  8. ^ "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.
  9. ^ a b c Tittarelli R, Mannocchi G, Pantano F, Romolo FS (January 2015). "Recreational use, analysis and toxicity of tryptamines". Curr Neuropharmacol. 13 (1): 26–46. doi:10.2174/1570159X13666141210222409. PMC 4462041. PMID 26074742. Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].
  10. ^ a b c d e Waters K (August 2021). "Pharmacologic Similarities and Differences Among Hallucinogens". J Clin Pharmacol. 61 Suppl 2: S100 – S113. doi:10.1002/jcph.1917. PMID 34396556. A study published in 2013 suggests that there may be a resurgence in use [of morning glory seeds] in the United States following its peak in the 1960s, potentially due to the low price, widespread availability, and lack of legal restrictions.45 [...] The mechanism of action of LSA remains unclear; its binding profile has some similarities to that of LSD, but LSA has demonstrated a lower affinity for all receptors.44 Although LSA may produce similar changes in visual perception as elicited by LSD, the psychedelic effects are weaker, likely due to the significantly higher affinity of LSD for 5HT2 receptors.44,45 [...] The seeds of these plants may be ingested whole, ground up, suspended in beverages, or formulated into capsules.11,46 A hallucinogenic dose of LSA ranges from 2 to 5 mg.35 This can generally be obtained from 5 to 10 seeds of Argyreia nervosa (0.14% LSA by dry weight) or 150 to 200 seeds of Ipomoea violacea (0.02% LSA by dry weight).35,47–49 The onset of effects is rapid, and the effects typically last from 4 to 8 hours.35
  11. ^ Paulke A, Kremer C, Wunder C, Toennes SW (August 2012). "Analysis of lysergic acid amide in human serum and urine after ingestion of Argyreia nervosa seeds". Anal Bioanal Chem. 404 (2): 531–538. doi:10.1007/s00216-012-6121-5. PMID 22695498.
  12. ^ a b Cite error: The named reference SmithTimmis1932 was invoked but never defined (see the help page).
  13. ^ a b c d e f g h i Steiner U, Leistner E (July 2018). "Ergot Alkaloids and their Hallucinogenic Potential in Morning Glories" (PDF). Planta Med. 84 (11): 751–758. Bibcode:2018PlMed..84..751S. doi:10.1055/a-0577-8049. PMID 29499587.
  14. ^ Grof S, Hofmann A (Fall 2001) [1984]. "Stanislav Grof Interviews Dr. Albert Hofmann". MAPS Bulletin. 9 (2): 22–35.
  15. ^ a b c d Shulgin A. "#26. LSD-25". TiHKAL. Erowid.org. Retrieved 2012-02-03. LA-111, ergine, d-lysergamide. This is an active compound and has been established as a major component in morning glory seeds. It was assayed for human activity, by Albert Hofmann in self-trials back in 1947, well before this was known to be a natural compound. An i.m. administration of a 500 microgram dose led to a tired, dreamy state with an inability to maintain clear thoughts. After a short period of sleep, the effects were gone and normal baseline was recovered within five hours. Other observers have confirmed this clouding of consciousness leading to sleep. The epimer, inverted at C-8, is isoergine or d-isolysergamide, and is also a component of morning glory seeds. Hofmann tried a 2 milligram dose of this amide, and as with ergine, he experienced nothing but tiredness, apathy, and a feeling of emptiness. Both compounds are probably correctly dismissed as not being a contributor to the action of these seeds. It is important to note that ergine, as well as lysergic acid itself, is listed as a Schedule III drug in the Controlled Substances Act, as a depressant. This is, in all probability, a stratagem to control them as logical precursors to LSD.
  16. ^ a b c d e f Hofmann A (1963). "The Active Principles of the Seeds of Rivea Corymbosa and Ipomoea Violacea". Botanical Museum Leaflets, Harvard University. 20 (6). Harvard University Herbaria: 194–212. doi:10.5962/p.168542. ISSN 0006-8098. JSTOR 41762231. Archived from the original on 28 March 2025.
  17. ^ a b c d Hofmann A (January–March 1971). "Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico". Bulletin on Narcotics. 23 (1): 3–14. Archived from the original on 28 March 2025.
  18. ^ Heacock RA (1975). "Psychotomimetics of the Convolvulaceae". Prog Med Chem. Progress in Medicinal Chemistry. 11: 91–118. doi:10.1016/s0079-6468(08)70209-1. ISBN 978-0-7204-7411-4. PMID 1078534. Archived from the original on 30 March 2025. Hofmann had previously described the action of synthetic ergine (1) as being primarily of a sedative nature [33]. A subcutaneous injection of 0.5-1.0 mg of (1) has been reported to produce a powerful hypnotic action, but a relatively weak psychedelic action [52]. [...] 33. A. Hofmann, Bot. Museum Leafl. Harvard Univ., 20 (1963) 194. [...] 52. J. Soleil and L. Lalloz, Prod. Probl. Pharm., 26 (1971) 682.
  19. ^ a b Cite error: The named reference ChenDeWitBos2020 was invoked but never defined (see the help page).
  20. ^ Moukaddam N, Ruiz P (2013). "Substance Use Disorders". International Handbook of Psychiatry. World Scientific. pp. 260–290. doi:10.1142/9789814405614_0011. ISBN 978-981-4405-60-7. Hawaiian baby woodrose (Argyreia nervosa) seeds contain d-lysergic acid amide (LSA, also known as d-lysergamide), which is a substance closely related to LSD. LSA can produce mild hallucinogenic effects and is considered a controlled substance in Ireland and the United Kingdom.
  21. ^ Perrine DM (2000). "Mixing the Kykeon" (PDF). ELEUSIS: Journal of Psychoactive Plants and Compounds. New Series 4: 9. Archived from the original (PDF) on 2019-07-20. Retrieved 2008-05-05.
  22. ^ Hofmann A (2009). LSD My Problem Child: Reflections on Sacred Drugs, Mysticism, and Science (4th ed.). MAPS.org. ISBN 978-0979862229.
  23. ^ Schultes RE (January 1969). "Hallucinogens of plant origin". Science. 163 (3864): 245–254. Bibcode:1969Sci...163..245E. doi:10.1126/science.163.3864.245. PMID 4883616. Archived from the original on 28 March 2025.
  24. ^ a b Cite error: The named reference Shulgin1976 was invoked but never defined (see the help page).
  25. ^ Ripinsky-Naxon M (1993). The Nature of Shamanism: Substance and Function of a Religious Metaphor. Albany, NY: State University of New York Press. p. 146. ISBN 9781438417417.
  26. ^ a b Cite error: The named reference HeimHeimannLukács1968 was invoked but never defined (see the help page).
  27. ^ Cite error: The named reference Shulgin2003 was invoked but never defined (see the help page).
  28. ^ "More Stipa Robusta". Entheogen Review. 8 (4): 136–. Winter 1999. Archived from the original on 28 March 2025. In The Botany and Chemistry of Hallucinogens by SCHULTES and HOFMANN, lysergic acid amide (ergine) is described as a strong tranquilizer with very little psychoactivity. HOFMANN should know; he is the "father of LSD" and did extensive research on related compounds. Ergine is not useful as an entheogen, but it's great for insomnia! Yet individuals persist in trying to use it as a vision-inducing material, simply because it is structurally related to LSD. — B. GREEN [...] This letter and the previous one bring up an interesting point. It is assumed by some that ergine is the primary visionary component in Ipomoea violacea and Argyreia nervosa. However, this may not be the case. K. TROUT has found that some morning glories are very LSD-like, and others are not (both within commercially available "heavenly blue" strains for example). There may be something else at work here that has not been adequately examined. It appears that HOFMANN did not evaluate all of the different chemicals found in I. violacea, and at least one that he did evaluate may have been visionary at doses higher than he took; he evaluated isoergine only up to the 2 mg level, and found it to be predominantly sedative without visual effects. JONATHAN OTT has pointed out that this compound might be psychoptic at higher levels (OTT 1993). We simply do not know at this point. It is also worth noting that lysergic acid-L-2-propanolamide, or ergonovine, has been reported as having mild visionary effects (as well as producing lassitude and leg cramps) in doses of 2–10 mg (HOFMANN 1978; BIGWOOD et al. 1979), and this compound is found in both Argyreia nervosa and Ipomoea violacea (CHAO & DER MARDEROSIAN 1973, listed under MOIR & DUDLEY'S synonym ergometrine), as is elymoclavine, which OTT has stated is "evidently psychoptic" (OTT 1993). Other possible players include the N-(1-hydroxyethyl)-amides of ergine and/or isoergine. The Botany and Chemistry of Hallucinogens notes: [...] Ergine may not be the psychoptic agent in morning glories that are active, or if it is then it is likely not the only player involved in producing visual activity. Between 1972 and 1983, K. TROUT ate Ipomoea violacea seeds or seed-extract several dozen times with wildly varying results ranging from powerfully colorful visuals to sedative effects. [...]
  29. ^ Stoll A, Hofmann A (1955). "Amide der stereoisomeren Lysergsäuren und Dihydro-lysergsäuren. 38. Mitteilung über Mutterkornalkaloide" [Amides of the stereoisomeric lysergic acids and dihydrolysergic acids. 38. Report on ergot alkaloids]. Helvetica Chimica Acta. 38 (2): 421–433. doi:10.1002/hlca.19550380207. ISSN 0018-019X. Archived from the original on 28 March 2025.
  30. ^ Cite error: The named reference Hofmann1980 was invoked but never defined (see the help page).
  31. ^ a b c Hoffer A, Osmond H (1967). "Chapter II A d-Lysergic Acid Diethylamide". The Hallucinogens. Academic Press. pp. 83–236. ISBN 9780123518507. OCLC 332437. OL 26708656M. The psychological properties of lysergic acid amide (LA) were compared to LSD and to lysergic acid monoethylamide (LAE) by Solms (1956). About 0.1-1.0 mg of LA given to male subjects, chiefly physicians and chemists, were required to produce a typical LA response. This dose was similar to the dose of LAE required. But LA produced more indifference, a decrease in motor activity and more sleepiness than LAE. The subjects fell asleep after 1 hour and if not aroused they slept about 2 hours. Higher doses caused autonomic changes, emesis, diarrhea and dizziness but no hallucinations. Subjects were sometimes irritable and depressed. Thus, when the methyl groups were removed and LA produced instead of LSD, the alkaloid had much less hallucinogenic and psychomotor activity and more sedative activity. [...] R. corymbosa is only one of a large number of morning glory varieties. After it was shown that LA and other ergot alkaloids were present, it became apparent to many investigators and to many more curious nonprofessionals that morning glory plants native to North America might also be active. Before long many varieties were sampled and it became generally known that certain varieties aptly named "Heavenly Blue," "Pearly Gates" and "Wedding Bells" were especially active psychologically. According to Cohen (1963) these discoveries initiated a wave of purchases of seeds from feed and seed stores. Federal agents seized many pounds of seeds in single raids. Psychotherapists who had used LSD for psychotherapy turned to the morning glory seeds when cut off from their normal sources. Stories appeared in the daily press and before long it became widely known how to obtain LSD-like experiences cheaply without having to get LSD.
  32. ^ Hofmann A, Tscherter H (1960). "Isolierung von Lysergsäure-Alkaloiden aus der mexikanischen Zauberdroge Ololiuqui (Rivea corymbosa (L.) Hall. f.)" [Isolation of lysergic acid alkaloids from the Mexican magic drug Ololiuqui (Rivea corymbosa (L.) Hall. f.)] (PDF). Experientia (in German). 16 (9): 414. doi:10.1007/BF02178840. ISSN 0014-4754. PMID 13715089. Retrieved 28 March 2025.
  33. ^ Juszczak GR, Swiergiel AH (2013-01-01). "Recreational use of D-lysergamide from the seeds of Argyreia nervosa, Ipomoea tricolor, Ipomoea violacea, and Ipomoea purpurea in Poland". Journal of Psychoactive Drugs. 45 (1): 79–93. doi:10.1080/02791072.2013.763570. PMID 23662334. S2CID 22086799.
  34. ^ Burillo-Putze G, López Briz E, Climent Díaz B, Munné Mas P, Nogue Xarau S, Pinillos MA, et al. (2013-09-01). "Drogas emergentes (III): plantas y hongos alucinógenos" [Emergent drugs (III): hallucinogenic plants and mushrooms]. Anales del Sistema Sanitario de Navarra. 36 (3): 505–518. doi:10.4321/s1137-66272013000300015. PMID 24406363.
  35. ^ "EMCDDA–Europol 2008 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). Europol. 2008. Retrieved 28 March 2025. 9. LSA ((8β)-9,10-didehydro-6-methyl-ergoline-8-carboxamide) – 29 October 2008 – Bulgaria
  36. ^ Cite error: The named reference Erowid-LSA was invoked but never defined (see the help page).
  37. ^ Cite error: The named reference USDOJ2021 was invoked but never defined (see the help page).
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