D-Lysergic acid N-(α-hydroxyethyl)amide

D-Lysergic acid N-(α-hydroxyethyl)amide

File:D LA OH ET.gif
Clinical data
Synonyms	D-lysergic acid methyl carbinolamide
Legal status
Legal status	In general: legal
Identifiers
IUPAC name 9,10-didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide
CAS Number	3343-15-5
PubChem CID	134553
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C18H21N3O2
Molar mass	311.378 g/mol
3D model (JSmol)	Interactive image
SMILES CC(NC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C)O

D-Lysergic acid α-hydroxyethylamide, also known as D-lysergic acid methyl carbinolamide, is an alkaloid of the ergoline family, and occurs in various species of vines of the Convolvulaceae and some species of fungi.

Chemistry

The chemical name for this alkaloid is 9,10-didehydro-N-(1-hydroxyethyl)-6-methylergoline-8-carboxamide. Its structure is very similar to LSD in that the N,N-diethylamide group is replaced with an N-(1-hydroxyethyl)amide in D-lysergic acid α-hydroxyethylamide.

Human Pharmacology

While animal data involving D-lysergic acid α-hydroxyethylamide exists, the physiological and pharmacological actions in humans are unknown. Animal studies do suggest the alkaloid may have some toxic effects at high levels.

Effects

The dominant alkaloids in the seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (tlitliltzin) are ergine (LSA) and isoergine (its epimer). Both are psychoactive but not psychedelic ergoline derivatives having mild sedative/vasoconstricting effects. The human activity of D-lysergic acid α-hydroxyethylamide is unknown.

Legality

D-lysergic acid α-hydroxyethylamide is unscheduled and uncontrolled in the United States, but possession and sales of it could be prosecuted under the Federal Analog Act because of its structural similarities to LSD and ergine. The legality of this drug, and other related substances, is under scrutiny as of July 2004, due to Operation Web Tryp.

See also

• Ergoline
• Ergot
• Lysergic acid
• Hallucinogenic drug
• Hawaiian baby woodrose (Argyreia nervosa)
• LSD
• Ololiuhqui (Rivea corymbosa)
• Tlitliltzin (Ipomoea violacea)

External links

• [http://research.lycaeum.org/researchpdfs/2343.pdf Ergot - A Rich Source of

Pharmacologically Active Substances] by Albert Hofmann