Lysergic acid 2,4-dimethylazetidide
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.[1][2] 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.[3]
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Other names | Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ |
Routes of administration | Oral |
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Formula | C21H25N3O |
Molar mass | 335.442 g/mol g·mol−1 |
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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".[4][5]
In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.[6][7] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[8]
Legal status
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.[7] 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[9], in Denmark as of May 2015 [10], and in Sweden as of January 26, 2016.[11]
References
- 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. 9 (1): 38–50. doi:10.1002/dta.1985. PMC 5411264. PMID 27265891.
- Fabrizio Schifano; Laura Orsolini; Duccio Papanti; John Corkery (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, 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
- ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
- Mike Power (2014-01-29). "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.
- "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in Danish). Lægemiddelstyrelsen. 31 August 2015.
- "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.