Lysergic acid 2,4-dimethylazetidide
|Systematic (IUPAC) name|
|Trade names||diazedine, lambda, LSZ|
(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".
On June 10th 2014 the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that LSZ be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying any harm associated with its use. The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.
- 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. p. 12. Retrieved 10 June 2014.