Ergine

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Ergine
Systematic (IUPAC) name
(8β)-9,10-didehydro-6-methyl-
ergoline-8-carboxamide
Identifiers
CAS number 478-94-4
ATC code  ?
PubChem 442072
Chemical data
Formula C16H17N3O 
Mol. mass 267.326 g/mol
Synonyms LSA, d-lysergic acid amide, d-lysergamide, Ergine, and LA-111
Pharmacokinetic data
Bioavailability  ?
Metabolism hepatic
Half life  ?
Excretion renal
Therapeutic considerations
Pregnancy cat.

X [1]
Legal status

Schedule III(US)
Routes Oral, 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 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 DEA schedule III drug in the United States.

Contents

[edit] History

A traditional use of morning glory seeds by Mexican Native Americans was first described by 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 sacraments by certain Zapotecs, 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 was recovered within five hours.[2] .

[edit] 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 endophytic fungus together with other ergot alkaloids [3].

It is also found in the seeds of several varieties of Morning Glories in doses of approximately 1 µg per seed.

[edit] Extraction

LSA can be extracted from morning glory (Ipomoea spp.) seeds[4] or Hawaiian baby woodrose[5].

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.[1] 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.

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 [2] to remove nauseatic effects from sources of LSA such as I. Tricolor seeds.

[edit] References

Smith, Sydney; Timmis, Geoffrey M. (1932). "98. The Alkaloids of Ergot. Part III. Ergine, a New Base obtained by the Degradation of Ergotoxine and Ergotinine.". J. Chem. Soc. 1932: 763-766. doi:10.1039/JR9320000763. 

Powell, William (2002). The Anarchist Cookbook. Ozark Press,LLC, 44. 

[edit] References

 This article needs additional citations for verification.
Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (July 2007)
  1. ^ Erowid (04-15-07). Erowid Morning Glory Basics.
  2. ^ Alexander Shulgin. TiHKAL #26.
  3. ^ Petroski RJ, Powell RG, Clay K (1992). "Alkaloids of Stipa robusta (sleepygrass) infected with an Acremonium endophyte". Nat. Toxins 1 (2): 84-88. doi:10.1002/nt.2620010205. PMID 1344912. 
  4. ^ Ask Erowid.
  5. ^ LSA Extraction.

[edit] See also

[edit] External links

v • d • e
Ergolines
Lysergic acid derivatives
Hallucinogenic lysergamides
Other ergolines
Natural sources