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

D-Lysergic acid N-(α-hydroxyethyl)amide
Systematic (IUPAC) name
9,10- didehydro- N- (1-hydroxyethyl)- 6- methylergoline- 8- carboxamide
Identifiers
CAS number	3343-15-5
ATC code	?
PubChem	134553
Chemical data
Formula	C18H21N3O2
Mol. mass	311.378 g/mol
SMILES	eMolecules & PubChem
Synonyms	D-lysergic acid methyl carbinolamide
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Legal
Routes	?

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 structure is similar to LSD, with the N,N- diethylamide group replaced by 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)^{[verification needed][citation needed]} are ergine (LSA) and isoergine (its epimer). 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)^{[verification needed][citation needed]}

External links

• Ergot - A Rich Source of Pharmacologically Active Substances by Albert Hofmann