LSZ

Lysergic acid 2,4-dimethylazetidide

Clinical data
Routes of administration	Oral
Legal status
Legal status	UK: Class A Illegal in Sweden and Switzerland
Identifiers
IUPAC name [(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
Synonyms	Lysergic acid 2,4-dimethylazetidine, Diazedine, Lambda, LSZ
​	freebase: (S,S)-isomer, freebase tartrate salt: (S,S)-isomer, tartrate salt
CAS Number	freebase: 470666-31-0 Y tartrate salt: 470666-32-1 N
PubChem CID	freebase: 71301249
ChemSpider	freebase: 30773535 N
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.442 g/mol
3D model (Jmol)	freebase: Interactive image
SMILES freebase: C[C@H]1C[C@@H](N1C(=O)[C@H]2CN([C@@H]3CC4=CNC5=CC=CC(=C45)C3=C2)C)C
InChI 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?)

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-HT_2A 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".

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.

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. 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 and in Sweden as of January 26, 2016.