Return of the lysergamides. Part II: Analytical and behavioural characterization of N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ)
Simon D. Brandt, Pierce V. Kavanagh, Folker Westphal, S. Elliott, Jason Wallach, Tristan Colestock, T. Burrow, S. J. Chapman, Alexander Stratford, D. Nichols, Adam L. Halberstadt
Drug Testing and Analysis June 6, 2016 DOI: 10.1002/dta.1985 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Population | Male C57BL/6J mice |
| Interventions | AL-LAD LSZ LSD |
| Dose | 200 µg/kg (maximal response); ED50 values: LSZ 114.2 nmol/kg, LSD 132.8 nmol/kg, AL-LAD 174.9 nmol/kg |
| Topics | LSD |
| Citations | 62 |
| Key findings | LSZ was equipotent to LSD and AL-LAD slightly less potent in eliciting head-twitch responses in mice. |
Abstract
Lysergic N,N-diethylamide (LSD) is perhaps one of the most intriguing psychoactive substances known and numerous analogs have been explored to a varying extent in previous decades. In 2013, N6-allyl-6-norlysergic acid diethylamide (AL-LAD) and (2’S,4’S)-lysergic acid 2,4-dimethylazetidide (LSZ) have appeared on the ‘research chemicals’ / new psychoactive substances (NPS) market in both powdered and blotter form. This study reports the analytical characterization of powdered AL-LAD and LSZ tartrate samples and their semi-quantitative determination on blotter paper. Included in this study was the use of nuclear magnetic resonance spectroscopy, gas chromatography mass spectrometry (MS), low and high-resolution electrospray MS(/MS), high performance liquid chromatography diode array detection and GC solid-state infrared analysis. One feature shared by serotonergic psychedelics, such as LSD, is the ability to mediate behavioral responses via activation of 5-HT2A receptors. Both AL-LAD and LSZ displayed LSD-like responses in male C57BL/6J mice when employing the head-twitch response (HTR) assay. AL-LAD and LSZ produced nearly identical inverted-U-shaped dose-dependent effects, with the maximal responses occurring at 200 µg/kg. Analysis of the dose-responses by nonlinear regression confirmed that LSZ (ED50 = 114.2 nmol/kg) was equipotent to LSD (ED50 = 132.8 nmol/kg) in mice, whereas AL-LAD was slightly less potent (ED50 = 174.9 nmol/kg). The extent to which a comparison in potency can be translated directly to humans requires further investigation. Availability of both chemical and pharmacological data obtained from NPS as they appear on the market provides important data to research communities that are interested in various aspects related substance use and forensic identification.
Comparable studies
Other preclinical and animal studies on LSD, most cited first.
Citations in the library
Cited by 41
- Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology May 1, 2020
- Designer drugs: mechanism of action and adverse effects Archives of Toxicology April 1, 2020
- Chronic pain and psychedelics: a review and proposed mechanism of action Regional Anesthesia & Pain Medicine May 4, 2020
- Effect of Hallucinogens on Unconditioned Behavior Current Topics in Behavioral Neurosciences 2016
- Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens. Current Topics in Behavioral Neurosciences 2017
and 36 more in the library
Cites 13
- Psychedelics and the Human Receptorome PLoS One 2010
- The new drug phenomenon Drug Testing and Analysis July 1, 2014
- Lysergamides of Isomeric 2,4-Dimethylazetidines Map the Binding Orientation of the Diethylamide Moiety in the Potent Hallucinogenic Agent N,N-Diethyllysergamide (LSD) Journal of Medicinal Chemistry September 1, 2002
- Structure–activity relationships of serotonin 5‐HT2Aagonists Wiley Interdisciplinary Reviews Membrane Transport and Signalling February 28, 2012
- Return of the lysergamides. Part I: Analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD) Drug Testing and Analysis October 12, 2015
and 8 more in the library