Ergine 373974 222530278 2008-06-29T21:01:14Z DOI bot 6652755 Citation maintenance. Formatted: title. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{drugbox | | width = 117 | image = Ergine.png | IUPAC_name = (8β)-9,10-didehydro-6-methyl-<br />ergoline-8-carboxamide | CAS_number = 478-94-4 | PubChem = 442072 | C=16 | H=17 | N=3 | O=1 | molecular_weight = 267.326 g/mol | synonyms = LSA, d-lysergic acid amide, d-lysergamide, Ergine, and LA-111 | metabolism = hepatic | excretion = renal | pregnancy_category= X <ref>{{cite web|url=http://www.erowid.org/plants/morning_glory/morning_glory_basics.shtml|author=Erowid|title=Erowid Morning Glory Basics|date=04-15-07}}</ref> | legal_US = Schedule III | legal_status = | routes_of_administration = [[Wiktionary:oral|Oral]], [[Wiktionary:intramuscular|Intramuscular]]}} '''LSA''', also known as '''d-lysergic acid amide''', '''d-lysergamide''', '''ergine''', and '''LA-111''', is an [[alkaloid]] of the [[ergoline]] family that occurs in various species of vines of the [[Convolvulaceae]] and some species of [[fungi]]. As the dominant alkaloid in the [[Psychedelics, dissociatives and deliriants|hallucinogenic]] seeds of ''[[Rivea corymbosa]]'' (ololiuhqui), ''[[Argyreia nervosa]]'' (Hawaiian baby woodrose) and ''[[Ipomoea tricolor]]'' (morning glories, tlitliltzin), it is often stated that ergine and/or isoergine (its [[epimer]]) is responsible for the psychedelic activity. In fact, the effects of synthetic LSA and iso-LSA are not particularly psychedelic, see ''Mixing the Kykeon'' below for a summary of human trials, and Chapter 17 and entry #26 of [[TiHKAL]] for further discussion. As a precursor to [[LSD]], ergine is a [[Drug Enforcement Administration|DEA]] schedule III drug in the [[United States]]. == History == <!-- [[Image:DSC 0018.JPG|300px|right|thumb|A closeup opened "Heavenly Blue" Morning Glory flower.]] [this may not be an ergine-containing but simply a toxic and possibly deadly species! --> A traditional use of morning glory seeds by Mexican Native Americans was first described by [[Richard Evans Schultes|Richard Schultes]] in 1941 in a short report documenting their use going back to [[Aztec]] times (cited in [[TiHKAL]] by [[Alexander Shulgin]]). Further research was published in 1960, when Don Thomes MacDougall reported that the seeds of ''[[Ipomoea tricolor]]'' were used as [[sacrament]]s by certain [[Zapotec]]s, sometimes in conjunction with the seeds of ''[[Rivea corymbosa]]'', another species which has a similar chemical composition, with [[lysergol]] instead of [[ergometrine]]. Ergine was assayed for human activity by [[Albert Hofmann]] in self-trials in 1947, well before it was known to be a natural compound. [[Intramuscular]] 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 (pharmacology)|baseline]] was recovered within five hours.<ref>{{cite web|url=http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml|title=TiHKAL #26|author=Alexander Shulgin}}</ref> . == Natural occurrence == Ergine has been found in high concentrations of 20 µg/g dry weight in the grass ''[[Stipa robusta]]'' (sleepygrass) infected with an ''[[Acremonium]]'' [[endophyte|endophytic]] [[fungus]] together with other ergot alkaloids <ref name="">{{cite journal | author = Petroski RJ, Powell RG, Clay K | year = 1992 | title = Alkaloids of ''Stipa robusta'' (sleepygrass) infected with an ''Acremonium'' endophyte | journal = Nat. Toxins | volume = 1 | issue = 2 | pages = 84–88 | pmid = 1344912 | doi = 10.1002/nt.2620010205 | url = http://www3.interscience.wiley.com/cgi-bin/abstract/112640007/ABSTRACT }}</ref>. It is also found in the seeds of several varieties of Morning Glories in concentrations of approximately 1 µg per seed. == Extraction == LSA can be extracted from morning glory ([[Ipomoea|''Ipomoea spp.]]) seeds<ref>{{cite web|url=http://www.erowid.org/ask/ask.php?ID=121|title=Ask Erowid}}</ref> or [[Hawaiian baby woodrose]]<ref>{{cite web|url=http://nepenthes.lycaeum.org/Extraction/extract2.html|title=LSA Extraction}}</ref>. The effects of the Ipomoea seed can be noticed after ingesting 50 seeds. 200 to 400 seeds is a standard dose, and there are reports of strong hallucinogenic side effects after ingestion of 400 to 1,000 seeds.{{ref}} Seeds of the Hawaiian Baby Woodrose contain much higher concentrations and will produce similar effects with 4-6 seeds. The experience duration can range from 4 to 12 hours, with mild effects occasionally lasting about a day and is usually accompanied with gastric discomfort, including severe nausea and [[flatulence]]. Other after effects of these seeds include sensitivity to light, and impaired motor skills. The removal of the outer coating of the seeds is often recommended to reduce such effects, although there appears to be no consensus as to this practice's efficacy and it has been suggested that it may not be true. Note: the fuzzy coating on the seeds can contain cyanogenic glycosides which can cause sickness in great enough quantities. Removal of non-polar solvent soluble compounds by soaking in solvent, filtration and allowing poisonous solvent to evaporate completely (Caution - Most non-polar solvents are very toxic) before consumption is reported [http://www.erowid.org] to remove nauseatic effects from sources of LSA such as ''I. Tricolor'' seeds. == References == {{cite journal|title=98. The Alkaloids of Ergot. Part III. Ergine, a New Base obtained by the Degradation of Ergotoxine and Ergotinine|journal=[[J. Chem. Soc.]]|date=1932|first=Sydney|last=Smith|coauthors=Timmis, Geoffrey M.|volume=1932|pages=763–766|doi=10.1039/JR9320000763}} {{cite book|last=Powell |first=William |authorlink=William_Powell_%28author%29 |title=[[The Anarchist Cookbook]] |publisher=Ozark Press,LLC |date=2002 |pages=44 |}} ==References== {{Refimprove|date=July 2007}} <references/> == See also == * [[List of Entheogens]] * [[Lysergic acid]] * [[Psychedelic plants]] * [[Tlitliltzin]] (''Ipomoea violacea'') == External links == * [http://www.erowid.org/plants/mushrooms/references/other/1971_hofmann_bulletin-narcotics.shtml Hofman, A. ''Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico'' Bulletin on Narcotics 1971 1 3] * [http://www.psychedelic-library.org/Mixing%20the%20Kykeon%20Final%20Draft.pdf Mixing the kykeon -- P. Webster, D. M. Perrine & C.A.P. Ruck] * [http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml TiHKAL (A & A Shulgin) #26] * [http://www.erowid.org/chemicals/lsa/lsa.shtml Erowid's LSA Vault] {{Ergolines}} [[Category:Alkaloids]] [[Category:Amides]] [[Category:Lysergamides]] [[Category:Serotonin receptor agonists]] [[de:Ergin]] [[et:LSA]] [[es:Amida de ácido D-lisérgico]] [[fr:Ergine]] [[it:Acido lisergico]] [[lt:LSA]] [[nl:Ergine]] [[ja:リゼルグ酸アミド]] [[no:LSA]] [[pl:Ergina]] [[pt:Ergina]] [[fi:LSA]] [[sv:LSA]]