Structure via PubChem · Public domain (PubChem)
ergine
Sign in to saveAlso known as LSA, d-lysergic acid amide, d-lysergamide
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.
Key facts
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 443731816
- Drug.image
- Ergine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 175px
- Drug.image2
- Ergine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.pregnancy_category
- X
- Drug.routes_of_administration
- Oral, intramuscular injection, subcutaneous injection
- Drug.class
- Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen; Sedative
- Drug.ATC_prefix
- None
- Drug.legal_BR
- F2
- Drug.legal_DE
- NpSG
- Drug.legal_UK
- Class A
- Drug.legal_US
- Schedule III
- Drug.legal_status
- Illegal in France
- Drug.metabolism
- Hepatic
via Wikipedia infobox
Chemical data
- Formula
- C16H17N3O
- Molecular weight
- 267.33 g/mol
- IUPAC name
- (6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
- SMILES
- CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N
- InChIKey
- GENAHGKEFJLNJB-QMTHXVAHSA-N
- XLogP
- 1.6
- Polar surface area
- 62.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 267.137162
Show 4 more facts
- chemical formula
- C₁₆H₁₇N₃O
- canonical SMILES
- CN1CC(C=C2C1CC3=CNC4=CC=CC2=C34)C(=O)N
- isomeric SMILES
- CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)N
- Commons category
- Ergines
Sources (2)
via Wikidata · CC0
~24 min read
Article
24 sectionsContents
- Use
- Effects
- Subjective effects
- Physiological effects
- Side effects
- Chemical coatings on seeds
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Chemistry
- Natural occurrence
- Biosynthesis
- History
- Society and culture
- Legal status
- Australia
- Canada
- New Zealand
- United Kingdom
- United States
- See also
- References
- External links
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.