Lysergic acid 2,4-dimethylazetidide

"LSZ" redirects here. For other uses, see LSZ (disambiguation).
Lysergic acid 2,4-dimethylazetidide
Systematic (IUPAC) name
(8β)-8-{[(2S,4S)-2,4-Dimethylazetidin-1-yl]carbonyl}-6-methyl-9,10-didehydroergoline
Clinical data
Trade names diazedine, lambda, LSZ
Routes of
administration		 oral
Legal status
Legal status
Identifiers
CAS Number 470666-31-0 YesY (S,S) isomer, freebase
470666-32-1 (S,S) isomer, tartrate salt
PubChem CID 10472143
ChemSpider 30773535 N
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. 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.[1]

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".[2][3]

In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.[4][5] 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.[5] 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.[7] and in Sweden as of 26. January 2016.[8]

See also

References

  1. ↑ Nichols, D. E.; Frescas, S.; Marona-Lewicka, D.; Kurrasch-Orbaugh, D. M. (Sep 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.
  2. ↑ Morris, H. (1 May 2011). "A Tour of Gordon Todd Skinner’s Subterranean LSD Palace". Vice Magazine. Retrieved 2011-06-15.
  3. ↑ Cole, Krystle (2005). Lysergic. Indianapolis: Dog Ear Publishing. ISBN 1-59858-007-8.
  4. ↑ LSZ Thread. UKChemicalResearch.org
  5. 1 2 ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Retrieved 10 June 2014.
  6. ↑ Mike Power. "The Drug Revolution That No One Can Stop".
  7. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien". Der Bundesrat.
  8. ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.
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