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
(8β)-8-{[(2S,4S)-2,4-Dimethylazetidin-1-yl]carbonyl}-6-methyl-9,10-didehydroergoline
Clinical data
Trade names diazedine, lambda, LSZ
Legal status
Routes of
administration		 oral
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
Molecular mass 335.442 g/mol
  • C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C
  • InChI=1S/C21H25N3O/c1-12-7-13(2)24(12)21(25)15-8-17-16-5-4-6-18-20(16)14(10-22-18)9-19(17)23(3)11-15/h4-6,8,10,12-13,15,19,22H,7,9,11H2,1-3H3/t12-,13-,15+,19+/m0/s1 N
  • Key:DUKNIHFTDAXJON-CTQRGLTFSA-N N
 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][unreliable source?][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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ LSZ Thread. UKChemicalResearch.org[unreliable source?]
  5. ↑ 5.0 5.1 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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