Welcome to the LSZ Thread
LSD (left) ; LSZ (right)
Formula = Lysergic Acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LSz) - Usually the (S,S)-(+) isomer
Bluelight Trip Reports:
- 1 1/2 blotters - First Time - Midnight Delight
- Untitled 450 ug LSZ report by The Shadow Self
- 450 ug report on First Time - "A Bit Much"
- 150 ug LSZ with Cannabis report - "Relaxing but Powerful Psychedelia"
- 150 ug LSZ report - "A Toe in the Water of LSZ"
- 600 ug LSZ report - "Good Visuals Difficult Body Trip" (very short)
- Isomer Design LSZ page for literature / articles and structural comparisons
- Dave Nichols - Psychedelic Science presentation on lysergic azetidide chemistry
Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD).
Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM.
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, IN 47907, USA. [email protected]
Lysergic acid amides were prepared from (R,R)-(-)-, (S,S)-(+)-, and cis-2,4-dimethyl azetidine. The dimethylazetidine moiety is considered here to be a rigid analogue of diethylamine, and thus, the target compounds are all conformationally constrained analogues of the potent hallucinogenic agent, N,N-diethyllysergamide, LSD-25. Pharmacological evaluation showed that (S,S)-(+)-2,4-dimethylazetidine gave a lysergamide with the highest LSD-like behavioral activity in the rat two lever drug discrimination model that was slightly more potent than LSD itself. This same diastereomer also had the highest affinity and functional potency at the rat serotonin 5-HT(2A) receptor, the presumed target for hallucinogenic agents, and a receptor affinity profile in a panel of screens that was most similar to that of LSD itself. Both cis- and the (R,R)-trans-dimethylazetidines gave lysergamides that were less potent in all relevant assays. The finding that the S,S-dimethylazetidine gave a lysergamide with pharmacology most similar to LSD indicates that the N,N-diethyl groups of LSD optimally bind when they are oriented in a conformation distinct from that observed in the solid state by X-ray crystallography. The incorporation of isomeric dialkylazetidines into other biologically active molecules may be a useful strategy to model the active conformations of dialkylamines and dialkylamides.
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