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Lysergic acid 2,4-dimethylazetidide
Clinical data
Other names	Lysergic 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
	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;
	freebase: (S,S)-isomer, freebase; tartrate salt: (S,S)-isomer, tartrate salt;
CAS Number	freebase: 470666-31-0 ; tartrate salt: 470666-32-1 ;
PubChem CID	freebase: 71301249;
ChemSpider	freebase: 30773535 ;
UNII	freebase: 8SWJ525W4R;
Chemical and physical data
Formula	C21H25N3O
Molar mass	335.451 g·mol−1
3D model (JSmol)	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 ; Key:DUKNIHFTDAXJON-CTQRGLTFSA-N ;
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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.^[2]^[3] 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.^[4]

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".^[5]^[6]

In 2013 LSZ also appeared on some designer drug and research chemical markets in the UK.^[7] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.^[8]

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.^[7] 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,^[9] in Denmark as of May 2015,^[10] and in Sweden as of January 26, 2016.^[11]