Lysergic acid 2,4-dimethylazetidide
|Systematic (IUPAC) name|
|Trade names||diazedine, lambda, LSZ|
|CAS Number||470666-31-0 (S,S) isomer, freebase
(S,S) isomer, tartrate salt: 470666-32-1
|Synonyms||Lysergic acid 2,4-dimethylazetidine|
|Molar 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".
In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.[unreliable source?] 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.
- Simon D. Brandt; Pierce V. Kavanagh; Folker Westphal; Simon P. Elliott; Jason Wallach; Tristan Colestock; Timothy E. Burrow; Stephen J. Chapman; Alexander Stratford; David E. Nichols; Adam L. Halberstadt (June 2016). "Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ)" (PDF). Drug Testing and Analysis. doi:10.1002/dta.1985. PMID 27265891.
- Fabrizio Schifano; Laura Orsolini; Duccio Papanti; John Corkery (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. Springer International Publishing. pp. 1–30. doi:10.1007/7854_2016_15. ISSN 1866-3370. OCLC 643052237. PMID 27272067.
- Nichols, D. E.; Frescas, S.; Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M. (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): 4344–4349. doi:10.1021/jm020153s. PMID 12213075.
- Morris, H. (1 May 2011). "Life Is a Cosmic Giggle on the Breath of the Universe". Vice Magazine. Retrieved 2011-06-15.
- Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 978-1598580075.
- LSZ Thread. UKChemicalResearch.org[unreliable source?]
- ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
- Mike Power. "The Drug Revolution That No One Can Stop".
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
- "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.