Lysergic acid 2,4-dimethylazetidide

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Lysergic acid 2,4-dimethylazetidide
LSD-azetidine.svg
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
Legal status
  • UK: Legal
  • US: Unregulated for non human use
Routes oral
Identifiers
CAS number 470666-31-0 YesY (S,S) isomer, freebase
470666-32-1 (S,S) isomer, tartrate salt
ATC code ?
PubChem CID 10472143
ChemSpider 30773535 N
Synonyms Lysergic acid 2,4-dimethylazetidine
Chemical data
Formula C21H25N3O 
Mol. mass 335.442 g/mol
 N (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][unreliable source?][5]

On June 10th 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.

References[edit]

  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[unreliable source?]
  5. ^ a b ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines". UK Home Office. p. 12. Retrieved 10 June 2014.