Lysergic acid 2,4-dimethylazetidide

Lysergic acid 2,4-dimethylazetidide
Clinical data
Other namesLysergic acid 2,4-dimethylazetidine; LSZ; LA-SS-Az; LA-Azetidide; LSD-Azetidide; Diazedine; Lambda
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
DrugBank
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)

Lysergic acid 2,4-dimethylazetidide, also known as LSZ, LA-SS-Az, or LA-Azetidide, 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.

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".

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