Lysergic acid 2,4-dimethylazetidide

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.

"LSZ" redirects here. For other uses, see LSZ (disambiguation).
Lysergic acid 2,4-dimethylazetidide
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, Sweden and Switzerland
Identifiers
  • [(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]-[(2S,4S)-2,4-dimethylazetidin-1-yl]methanone
​
  • 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)
  • freebase: C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C
  • freebase: 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
 NY (what is this?)  (verify)

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".

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.

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