Ergine

Ergine
Clinical data
Other namesLysergic acid amide; LSA; LAA; ᴅ-Lysergic acid amide; ᴅ-Lysergamide, d-Lysergamide; LA-111; "Lacy"; 6-Methyl-9,10-didehydroergoline-8β-carboxamide
Pregnancy
category
  • X
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)
Duration of action4–10 h (morn. glory seeds)
ExcretionUrine
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
Chemical and physical data
FormulaC16H17N3O
Molar mass267.332 g·mol−1
3D model (JSmol)
Melting point135 °C (275 °F) Decomposes
  • 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 Y
  • Key:GENAHGKEFJLNJB-QMTHXVAHSA-N Y
  (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). Ergine is an ergoline alkaloid found in fungi such as Claviceps paspali (ergot) and Periglandula species such as Periglandula clandestina, which are permanently connected with many morning glory vines. Ergine induces relatively mild psychedelic effects as well as pronounced sedative effects.

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). Morning glory seeds have a history of entheogenic use in Mesoamerica dating back at least hundreds of years. They have also since been used by many Westerners. In addition to ergine, morning glory seeds contain other ergolines such as lysergic acid hydroxyethylamide (LSH), lysergic acid propanolamide (ergonovine), and isoergine. Some of these compounds are pharmacologically active and are thought to contribute to the effects of the seeds as well. There has been debate about the role of ergine in causing the psychedelic effects of morning glory seeds.

Ergine was first described by Sidney Smith and Geoffrey Timmis after they isolated it from ergot in 1932. It was first synthesized subsequent to its isolation in the 1930s. 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. He and his colleagues also isolated ergine from morning glory seeds in 1960. Morning glory seeds started to become frequently used as a recreational drug that same year and has been widely used since. Recreational use of morning glory seeds may be increasing due to their inexpensiveness, widespread availability, and lack of legal restrictions. Ergine has been encountered as a novel designer drug in Europe. Ergine, though not morning glory seeds, has become a controlled substance in various places in the world.