Lysergic acid 2,4-dimethylazetidide

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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.[1][2] 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.[3]

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".[4][5]

Dosage and effects

The dosage of LSZ in humans is said to be 100 to 300Script error: No such module "String".μg orally, which is higher than the listed dosage of LSD (60–200Script error: No such module "String".μg).[6][7] According to David E. Nichols, LSZ is about equipotent with LSD in humans.[8] Hence, unlike in rodents, LSZ does not appear to be more potent than LSD in humans.[6]

Pharmacology

LSZ activities
Target Affinity (Ki, nM)
5-HT1A 0.45
5-HT1B 2.4
5-HT1D 2.4
5-HT1E 276
5-HT1F ND
5-HT2A 0.54–19.2 (Ki)
0.32–957 (EC50Tooltip half-maximal effective concentration)
56–85% (EmaxTooltip maximal efficacy)
5-HT2B 27 (Ki)
0.4–58.4 (EC50)
57–74% (Emax)
5-HT2C 37 (Ki)
992 (EC50)
39% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 27.3
5-HT6 14.5
5-HT7 14.3
α1A 850.2
α1B >10,000
α1D–α2C ND
β1 75.8
β2 1,069
β3 ND
D1 292
D2 73.6–110
D3 6.0
D4 36–95.5
D5 402.2
H1 2,504
H2–H4 ND
M1–M5 ND
I1 ND
σ1, σ2 ND
TAAR1Tooltip Trace amine-associated receptor 1 ND
SERTTooltip Serotonin transporter >10,000 (Ki)
NETTooltip Norepinephrine transporter >10,000 (Ki)
DATTooltip Dopamine transporter >10,000 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [9][10][11][3][12][13][14][15][16]

LSZ produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[6] It shows about the same potency as LSD in producing this effect.[6] However, LSZ shows a weaker maximal HTR than LSD or AL-LAD in terms of magnitude.[1] The drug also substitutes for LSD in rodent drug discrimination tests.[6][3] It was about 1.8-fold more potent than LSD in this assay.[6][3]

History

In 2013, LSZ also appeared on some designer drug and research chemical markets in the United Kingdom.[17] LSZ later gained international popularity through a small cluster of mail-order novel psychedelic shops that appeared in 2012.[18]

Society and culture

Legal status

United Kingdom

On June 10, 2014, the United Kingdom 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.[17] 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.

Switzerland

LSZ is illegal in Switzerland as of December 2015,[19] in Denmark as of May 2015,[20] and in Sweden as of January 26, 2016.[21]

See also

References

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  20. ↑ Script error: No such module "citation/CS1".
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External links

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