Lysergic acid 2,4-dimethylazetidide Clinical data Other names Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ Routes of administration Oral Legal status Legal status
[(6a R,9 R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]-[(2 S,4 S)-2,4-dimethylazetidin-1-yl]methanone freebase: ( S, S)-isomer, freebase tartrate salt: ( S, S)-isomer, tartrate salt CAS Number PubChem CID ChemSpider Chemical and physical data Formula C 21 H 25 N 3 O Molar mass 335.442 g/mol g·mol −1 3D model ( JSmol)
(what is this?) (verify) 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-HT 2A receptor. There are three possible stereoisomers around the azetidine ring, with the ( being the most active, slightly more S, S)-(+) isomer 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". 
In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.
 LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012. 
On June 10, 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.
LSZ is illegal in Switzerland as of December 2015,
in Denmark as of May 2015,  and in Sweden as of January 26, 2016. 
Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, et al. (January 2017). "6 -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ)" (PDF). Drug Testing and Analysis. 9 (1): 38–50. doi: 10.1002/dta.1985. PMC . 5411264 PMID 27265891.
Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. Springer International Publishing. pp. 351–380. doi: 10.1007/7854_2016_15. ISBN . 978-3-319-52442-9 OCLC 643052237. PMID 27272067.
Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM (September 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): 4344–9. doi: 10.1021/jm020153s. PMID 12213075.
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