LSZ

LSZ
	Structure of LA-SS-Az (trans-(S,S)-LSZ), the most active and commonly used isomer of LSZ
	Ball-and-stick model of LSZ
Clinical data
Other names	Lysergic acid 2,4-dimethylazetidine; Lysergic acid 2S,4S-dimethylazetidine; LSZ; LA-Azetidide; LSD-Azetidide; LA-SS-Az; SS-LSZ; (S,S)-LSZ; Diazedine; λ; Lambda
Routes of; administration	Oral
Drug class	Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A; Illegal in Denmark, France, Sweden, and Switzerland;
Pharmacokinetic data
Duration of action	3–11 hours (median 8 hours)
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;
DrugBank	freebase: DB15196;
ChemSpider	freebase: 30773535 ;
UNII	freebase: 8SWJ525W4R;
CompTox Dashboard (EPA)	freebase: DTXSID201026958 ;
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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LSZ, also known as lysergic acid 2,4-dimethylazetidide or as LA-Azetidide (LA-Az), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is taken orally.

The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT_2A receptor. It also interacts with dopamine receptors. The compound is a close analogue of LSD that has been modified at the amide to be more rigid and to have three diastereomers. LA-SS-Az, the (S,S)- isomer, is the most potent and similar isomer to LSD, and is the typically employed form of LSZ. LA-SS-Az and the other isomers of LSZ produce psychedelic-like effects in animals.

LSZ was first described in the scientific literature by David E. Nichols and colleagues in 2002. It was developed as a tool for studying psychedelic interactions with the serotonin 5-HT_2A receptor and followed the earlier unstable compound LA-Aziridine developed by Nichols and Robert Oberlender. LSZ, under the name "diazedine", may have been produced on a small scale by the LSD manufacturers William Leonard Pickard and Gordon Todd Skinner around the year 2000. It was first definitely encountered as a novel designer drug in 2013 and then became a popular psychedelic. LSZ is a controlled substance in several European countries.