Ergine

Ergine
Systematic (IUPAC) name
(8β)-9,10-didehydro-6-methyl-
ergoline-8-carboxamide
Clinical data
Pregnancy
category
Routes of
administration		 Oral, Intramuscular
Legal status
Legal status
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
CAS Number 478-94-4 YesY
ATC code none
PubChem CID 442072
ChemSpider 390611 YesY
ChEBI CHEBI:4819 YesY
ChEMBL CHEMBL227213 YesY
Synonyms LSA, d-lysergic acid amide, d-lysergamide, Ergine, and LA-111
Chemical data
Formula C16H17N3O
Molar mass 267.326 g/mol
Physical data
Melting point 135 °C (275 °F) Decomposes[2]
  (verify)

Ergine, also known as d-lysergic acid amide (LSA) and d-lysergamide, 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 psychedelic seeds of Turbina 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. However, this theory is debatable, as anecdotal reports suggest that the effects of synthetic LSA and iso-LSA are only slightly psychedelic, see Mixing the Kykeon below for a summary of human trials, and Chapter 17 and entry #26 of TiHKAL for further discussion.

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.[3]

In 1956, the Central Intelligence Agency conducted research on the psychedelic properties of the ergine in the seeds of Rivea corymbosa, as Subproject 22 of MKULTRA.

Shamanic stories say Ipomoea purpurea seeds, when swallowed or chewed, may incite a mild trip where synesthesia occurs and eye imagery is enhanced.[4]

Legal status

As a precursor to LSD, ergine is a DEA schedule III drug in the United States, and is considered a depressant.

Biosynthesis

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.[5]

Ergine is a component of the alkaloids contained in the Claviceps purpurea (Ergot) fungus which grows on the heads of infected rye grasses.

It is also found in the seeds of several varieties of morning glories in concentrations of approximately 10 µg per seed, as well as Hawaiian baby woodrose seeds, at a concentration of around 0.13% of dry weight.[6]

Known fatalities

There are no known deaths associated directly with pharmacological causes of ergine, but rather due to self-harm, impaired judgement, and drug interactions. One known case involves suicide after ingestion of morning glory seeds.[7] Another instance is a death due to falling off of a building after ingestion of Hawaiian baby woodrose seeds and alcohol.[8]

See also

Notes

References

  1. ↑ Erowid Morning Glory Basics, Erowid.org, retrieved 2012-02-03
  2. ↑ Smith, Sydney; Timmis, Geoffrey Millward (1932). "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): 763. doi:10.1039/jr9320000763.
  3. ↑ Alexander Shulgin, "#26. LSD-25", TiHKAL, Erowid.org, retrieved 2012-02-03
  4. ↑ Erowid Psychoactive Vaults, Erowid.org, retrieved 2012-02-03
  5. ↑ 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.
  6. ↑ Chao JM, Der Marderosian AH (1973). "Ergoline alkaloidal constituents of Hawaiian baby wood rose, Argyreia nervosa (Burmf) Bojer". J. Pharm. Sci. 62 (4): 588–91. doi:10.1002/jps.2600620409.
  7. ↑ Cohen, Sidney (1964). "SUICIDE FOLLOWING MORNING GLORY SEED INGESTION". The American Journal of Psychiatry 120 (1). Retrieved 12 April 2013.
  8. ↑ Klinke, Helene; Irene Breum Müller; Steffen Steffenrud; Rasmus Dahl-Sørensen (15 April 2010). "Two cases of lysergamide intoxication by ingestion of seeds from Hawaiian Baby Woodrose". Forensic Science International 197 (1): e1–e5. doi:10.1016/j.forsciint.2009.11.017. Retrieved 12 April 2013.

External links

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