Buy LSZ Cas-470666-31-0 Cas-470666-32-1
Buy LSZ Cas-470666-31-0 Cas-470666-32-1
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).[4][5][6][7] It is taken orally.[1][2]
The drug acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor.[4][7] It also interacts with dopamine receptors.[7][8] The compound is a close analogue of LSD that has been modified at the amide to be more rigid and to have three diastereomers.[4][6][7] LA-SS-Az, the (S,S)- isomer, is the most potent and similar isomer to LSD, and is the typically employed form of LSZ.[5][6][7] LA-SS-Az and the other isomers of LSZ produce psychedelic-like effects in animals.[7][6]
LSZ was first described in the scientific literature by David E. Nichols and colleagues in 2002.[6][7] It was developed as a tool for studying psychedelic interactions with the serotonin 5-HT2A receptor and followed the earlier unstable compound LA-Aziridine developed by Nichols and Robert Oberlender.[4][7][9][10][11] 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.[12][13][14] It was first definitely encountered as a novel designer drug in 2013 and then became a popular psychedelic.[6][15][16][2] LSZ is a controlled substance in several European countries.[17][18][19][20]
Use and effects
LSZ, as the (S,S)- isomer LA-SS-Az, has been reported to have a dose range of 100 to 200 μg or 100 to 300 μg orally, with a typical dose estimate of 150 or 200 μg.[1][2][6] This dose range is notably higher than that of LSD, which is 50 to 200 μg with a typical dose of about 100 μg.[21][22][23][24][1] According to David E. Nichols however, LSZ is approximately equipotent with LSD based on human anecdotal reports.[5] The duration of LSZ is reported to be in the range of 3 to 11 hours, with a median duration of around 8 hours.[2] This was shorter than the duration of the LSD prodrug 1P-LSD, which had a duration range of 6 to 14 hours and a median duration of about 10 hours in the same study.[2] The detailed effects of LSZ, aside from it being a psychedelic similarly to LSD, do not appear to have been reported in the published literature.[1][2][4]
Interactions
Pharmacology
Pharmacodynamics
| 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: [25][26][27][7][8][28][29][30][4] | |
LSZ has been found to bind non-selectively to serotonin, dopamine, and certain other receptors.[7][27][8][28] It shows especially high affinity for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors, among others.[7][27][8] The drug acts as a potent agonist of the serotonin 5-HT2A and 5-HT2C receptors, with potency and efficacy similar to that of LSD.[7][8][28] It may be more potent than LSD as an agonist of the serotonin 5-HT1A receptor.[7]
LSZ produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[31][1][6] It shows about the same potency as LSD and AL-LAD in producing this effect.[31][1] However, LSZ shows a weaker maximal head-twitch response than LSD or AL-LAD.[6] This might be due to lower efficacy at the serotonin 5-HT2A receptor or stronger actions at other receptors like the serotonin 5-HT1A or 5-HT2C receptor.[6] LSZ also substitutes for LSD in rodent drug discrimination tests.[1][7] It was about 1.8-fold more potent than LSD in this assay.[1][7] All three isomers of LSZ fully substituted for LSD in rodent drug discrimination tests, but the (S,S)- isomer was the most potent and was the only isomer that was more potent than LSD.[6][7] In addition, only the (S,S) isomer fully substituted for the LSD-like selective serotonin 5-HT1A receptor full agonist and partial ergoline LY-293284.[6][7] In contrast to LSZ, LSD itself does not substitute for LY-293284 in drug discrimination tests.[7]
In addition to its psychedelic effects, LSZ has been found to produce anti-inflammatory effects in preclinical research.[6][32]
Pharmacokinetics
The in-vitro metabolism of LSZ has been studied.[33]
Chemistry
LSZ, also known as lysergic acid 2,4-dimethylazetidide or as LA-Azetidine (LA-Az), is a substituted lysergamide derivative related to lysergic acid diethylamide (LSD).[34][6][7] It is the analogue of LSD in which the N,N–diethylamide moiety has been replaced with an 2,4-dimethylazetidine moiety.[34][6][7] The compound has three possible diastereomers around the azetidine ring, including the cis-(2RS,4SR)-, trans-(2R,4R)-, and trans-(2S,4S)- 2,4-dimethylazetidine isomers.[35][6][7] The (S,S)- isomer, also known as LA-SS-Az, is the most potent diastereomer and is the typically employed form of the compound.[6][7]
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