Lysergic acid 2,4-dimethylazetidide explained

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. LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[6]

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,[8] in Denmark as of May 2015,[9] and in Sweden as of January 26, 2016.[10]

See also

Notes and References

  1. Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL . 6 . 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) . Drug Testing and Analysis . 9 . 1 . 38–50 . January 2017 . 27265891 . 5411264 . 10.1002/dta.1985 . PDF .
  2. Book: https://link.springer.com/bookseries/7854 . 10.1007/7854_2016_15 . 27272067 . 32 . Springer International Publishing . Schifano F, Orsolini L, Papanti D, Corkery J . Neuropharmacology of New Psychoactive Substances (NPS) . June 2016 . 351–380 . 643052237 . NPS: Medical Consequences Associated with Their Intake. 978-3-319-52442-9 . Current Topics in Behavioral Neurosciences .
  3. Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM . Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) . Journal of Medicinal Chemistry . 45 . 19 . 4344–4349 . September 2002 . 12213075 . 10.1021/jm020153s .
  4. Web site: Life Is a Cosmic Giggle on the Breath of the Universe . Morris H . Vice Magazine . 1 May 2011. 2011-06-15.
  5. Book: Cole K . 2005 . Lysergic . Dog Ear Publishing . Indianapolis . 978-1598580075.
  6. Web site: The Drug Revolution That No One Can Stop. Power M . 2014-01-29.
  7. Web site: Update of the Generic Definition for Tryptamines . UK Home Office . 10 June 2014 . 10 June 2014 . ACMD. 12.
  8. Web site: Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien . Der Bundesrat . German.
  9. Web site: Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet . Lægemiddelstyrelsen . Danish . 31 August 2015.
  10. Web site: 31 nya ämnen kan klassas som narkotika eller hälsofarlig vara . Folkhälsomyndigheten . Swedish . November 2015.

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