LSD optical isomers & racemer reclamation

[timnickbear]

SWIM was wondering if anyone knew a link to any possible information regarding lysergic acid sec-butylamide and iso-lysergic acid sec-butylamide or 1-acetyl-LSD and or their respective emetic acitivities, and SWIM knows ALD-52 to be @ 91%.  Any experimental data would be useful also. Also any Bees who know a bit about Nick that woould know the way in which he accomlished the epimerization of iso-LSD by dissolving potassium metal in anhydrous ether and then refluxed with anhydrous methanol. After returning to room temperature the iso-LSD was added to the potassium solution and allowed to sit 24 hours at room temperature in the dark, providing a "98.5%" conversion. Swim would be very appreciative for this information.

[Rhodium]

Distinction of Some Dialkyl Amides of Lysergic and iso-Lysergic Acids from LSD
K. Bailey, D. Verner, D. Legault

Journal of the Association of Official Analytical Chemists, 56(1), 88-99 (1973)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/lysergamide.distinction.pdf)

Abstract
The 10 lysergic and iso-lysergic acid amides described are N,N-dimethyl, N,N-diethyl-, N-Methyl-N-Propyl, N-Ethyl-N-Propyl and N,N-dipropyl. Their ultraviolet spectra are insufficiently different for distinction. Mass spectra do not readily differentiate between isomers. Proton Magnetic Resonance Spectra are distinct and provide a positive structural identification of the amide. Their infrared spectra are similar, but suitable for distinguishing these compounds from LSD. Various reference spectra are provided. Thin layer and gas-liquid chromatographic systems suitable for distinguishing these compounds from LSD are described.

[Rhodium]

Isolation and Identification of Lysergic Acid Amide and Isolysergic Acid Amide as the Principal Ergoline Alkaloids in Argyreia nervosa, a Tropical Wood Rose
Michael D. Miller

Journal of the Association of Official Analyical Chemists, Vol. 53, No. 1, 123-127 (1970)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/forensic/lsa.hbwr.jaoac.pdf)

Abstract
Lysergic acid amide and isolysergic acid amide have been extracted and isolated from the seed of Hawaiian baby wood rose. The ergoline alkaloids were identified by TLC, melting point determination, and UV and IR spectrophotometry.