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

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D-Lysergic acid N-(α-hydroxyethyl)amide
Clinical data
SynonymsD-lysergic acid methyl carbinolamide
Legal status
Legal status
  • In general: legal
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
Molar mass311.378 g/mol
3D model (JSmol)

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.


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.


The dominant alkaloids in the seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (tlitliltzin)[verification needed][citation needed] 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.


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

External links

Pharmacologically Active Substances] by Albert Hofmann