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Ergine
Systematic (IUPAC) name
(8β)-9,10-didehydro-6-methyl- ergoline-8-carboxamide
Identifiers
CAS number	?
ATC code	?
PubChem	?
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.

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] .

Ergine has been found in high concentrations of 20 mg/kg dry weight in the grass Stipa robusta (sleepygrass) infected with an Acremonium endophytic fungus together with other ergot alkaloids ^[3].

LSA can be extracted from morning glory seeds^[4] or Hawaiian baby woodrose^[5].

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. 

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.

• List of Entheogens
• Lysergic acid
• Psychedelic plants
• Tlitliltzin (Ipomoea violacea)

• Hofman, A. Teonanácatl and Ololiuqui, two ancient magic drugs of Mexico Bulletin on Narcotics 1971 1 3
• Mixing the kykeon -- P. Webster, D. M. Perrine & C.A.P. Ruck
• TiHKAL (A & A Shulgin) #26
• Erowid's LSA Vault