Chemistry:Lysergic acid 2,4-dimethylazetidide

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Short description: Chemical compound


Lysergic acid 2,4-dimethylazetidide
LSD-azetidine.svg
Clinical data
Other namesLysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ
Routes of
administration		Oral
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • Illegal in Denmark, France,[1] Sweden and Switzerland
Identifiers
​
  • freebase: (S,S)-isomer, freebase
  • tartrate salt: (S,S)-isomer, tartrate salt
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H25N3O
Molar mass335.451 g·mol−1
3D model (JSmol)
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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.[2][3] 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.[4]

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".[5][6]

In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.[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]

See also

References

  1. ↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" (in fr). 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554. 
  2. ↑ "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. January 2017. doi:10.1002/dta.1985. PMID 27265891. 
  3. ↑ "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. Springer International Publishing. June 2016. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. https://link.springer.com/bookseries/7854. 
  4. ↑ "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. doi:10.1021/jm020153s. PMID 12213075. 
  5. ↑ "Life Is a Cosmic Giggle on the Breath of the Universe". Vice Magazine. 1 May 2011. https://www.vice.com/en_ca/read/life-is-a-cosmic-giggle-803-v18n5/page/3. 
  6. ↑ Lysergic. Indianapolis: Dog Ear Publishing. 2005. ISBN 978-1598580075. 
  7. ↑ 7.0 7.1 ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office. p. 12. https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf. 
  8. ↑ "The Drug Revolution That No One Can Stop". 2014-01-29. https://medium.com/matter/the-drug-revolution-that-no-one-can-stop-19f753fb15e0. 
  9. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  10. ↑ "Bekendtgørelse om euforiserende stoffer - ni nye stoffer tilføjet" (in Danish). Lægemiddelstyrelsen. 31 August 2015. https://laegemiddelstyrelsen.dk/da/nyheder/2015/bekendtgoerelse-om-euforiserende-stoffer-ni-nye-stoffer-tilfoejet/. 
  11. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2015/november/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/. 



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