Lysergic acid 2,4-dimethylazetidide

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"LSZ" redirects here. For other uses, see LSZ (disambiguation).
Lysergic acid 2,4-dimethylazetidide
LSD-azetidine.svg
Systematic (IUPAC) name
[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]-[(2S,4S)-2,4-dimethylazetidin-1-yl]methanone
Clinical data
Trade names diazedine, lambda, LSZ
Routes of
administration
oral
Legal status
Legal status
  • UK: Class A
  • Illegal in Sweden and Switzerland
Identifiers
CAS Number 470666-31-0 YesY (S,S) isomer, freebase
(S,S) isomer, tartrate salt: 470666-32-1
PubChem CID 71301249
ChemSpider 30773535 YesY
Synonyms Lysergic acid 2,4-dimethylazetidine
Chemical data
Formula C21H25N3O
Molar mass 335.442 g/mol
 NYesY (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.[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]

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][unreliable source?][7] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[8]

Legal Status[edit]

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] and in Sweden as of 26. January 2016.[10]

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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. 
  4. ^ Morris, H. (1 May 2011). "Life Is a Cosmic Giggle on the Breath of the Universe". Vice Magazine. Retrieved 2011-06-15. 
  5. ^ Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 978-1598580075. 
  6. ^ LSZ Thread. UKChemicalResearch.org[unreliable source?]
  7. ^ a b ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014. 
  8. ^ Mike Power. "The Drug Revolution That No One Can Stop". 
  9. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. 
  10. ^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.