Lysergic acid 2,4-dimethylazetidide
|Systematic (IUPAC) name|
|Trade names||diazedine, lambda, LSZ|
|Legal status||Legal (UK) Unregulated for non human use (US)|
(S,S) isomer, freebase|
470666-32-1 (S,S) isomer, tartrate salt
|Synonyms||Lysergic acid 2,4-dimethylazetidine|
|Mol. mass||335.442 g/mol|
|(what is this?)|
Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.
There have been several unconfirmed reports of lysergic acid 2,4-dimethylazetidide being synthesized in illicit laboratories and distributed on blotter paper or in liquid solution under names such as "diazedine" and "λ".
- Nichols, D. E.; Frescas, S.; Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M. (Sep 2002). "Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent N,N-Diethyllysergamide (LSD)" (PDF). Journal of Medicinal Chemistry 45 (19): 4344–4349. doi:10.1021/jm020153s. PMID 12213075.
- Morris, H. (1 May 2011). "A Tour of Gordon Todd Skinner’s Subterranean LSD Palace". Vice Magazine. Retrieved 2011-06-15.
- Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 1-59858-007-8.
- LSZ Thread. UKChemicalResearch.org[unreliable source?]
- ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office. Retrieved 10 June 2014.