Literature DB >> 32180350

Return of the lysergamides. Part VI: Analytical and behavioural characterization of 1-cyclopropanoyl-d-lysergic acid diethylamide (1CP-LSD).

Simon D Brandt1, Pierce V Kavanagh2, Folker Westphal3, Alexander Stratford4, Anna U Odland5, Adam K Klein6, Geraldine Dowling2,7, Nicola M Dempster1, Jason Wallach8, Torsten Passie9,10, Adam L Halberstadt6,11.   

Abstract

Lysergic acid diethylamide (LSD) is a prototypical serotonergic psychedelic drug and the subject of many clinical investigations. In recent years, a range of lysergamides has emerged with the production of some being inspired by the existing scientific literature. Others, for example various 1-acyl substituted lysergamides, did not exist before their appearance as research chemicals. 1-Cylopropanoyl-LSD (1CP-LSD) has recently emerged as a new addition to the group of lysergamide-based designer drugs and is believed to be psychoactive in humans. In this investigation, 1CP-LSD was subjected to detailed analytical characterizations including various mass spectrometry (MS) platforms, gas and liquid chromatography, nuclear magnetic resonance spectroscopy, solid phase and GC condensed phase infrared spectroscopy. Analysis by GC-MS also revealed the detection of artificially induced degradation products. Incubation of 1CP-LSD with human serum led to the formation of LSD, indicating that it may act as a prodrug for LSD in vivo, similar to other 1-acyl substituted lysergamides. The analysis of blotters and pellets is also included. 1CP-LSD also induces the head-twitch response (HTR) in C57BL/6 J mice, indicating that it produces an LSD-like behavioural profile. 1CP-LSD induced the HTR with an ED50 = 430.0 nmol/kg which was comparable to 1P-LSD (ED50 = 349.6 nmol/kg) investigated previously. Clinical studies are required to determine the potency and profile of the effects produced by 1CP-LSD in humans.
© 2020 John Wiley & Sons, Ltd.

Entities:  

Keywords:  5-HT2A receptor; LSD; lysergamides; new psychoactive substances; psychedelics

Mesh:

Substances:

Year:  2020        PMID: 32180350      PMCID: PMC9191646          DOI: 10.1002/dta.2789

Source DB:  PubMed          Journal:  Drug Test Anal        ISSN: 1942-7603            Impact factor:   3.234


  27 in total

1.  Pharmacology of lysergic acid diethylamide and some of its related compounds.

Authors:  E ROTHLIN
Journal:  J Pharm Pharmacol       Date:  1957-09       Impact factor: 3.765

2.  Hallucinogens recruit specific cortical 5-HT(2A) receptor-mediated signaling pathways to affect behavior.

Authors:  Javier González-Maeso; Noelia V Weisstaub; Mingming Zhou; Pokman Chan; Lidija Ivic; Rosalind Ang; Alena Lira; Maria Bradley-Moore; Yongchao Ge; Qiang Zhou; Stuart C Sealfon; Jay A Gingrich
Journal:  Neuron       Date:  2007-02-01       Impact factor: 17.173

Review 3.  Lysergamides revisited.

Authors:  R C Pfaff; X Huang; D Marona-Lewicka; R Oberlender; D E Nichols
Journal:  NIDA Res Monogr       Date:  1994

4.  Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response.

Authors:  Adam L Halberstadt; Mark A Geyer
Journal:  Neuropharmacology       Date:  2013-09-04       Impact factor: 5.250

5.  Species differences in hydrolysis of isocarbacyclin methyl ester (TEI-9090) by blood esterases.

Authors:  T Minagawa; Y Kohno; T Suwa; A Tsuji
Journal:  Biochem Pharmacol       Date:  1995-05-17       Impact factor: 5.858

6.  Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD).

Authors:  Simon D Brandt; Pierce V Kavanagh; Folker Westphal; Alexander Stratford; Simon P Elliott; Geraldine Dowling; Jason Wallach; Adam L Halberstadt
Journal:  Drug Test Anal       Date:  2019-06-18       Impact factor: 3.345

Review 7.  Effect of Hallucinogens on Unconditioned Behavior.

Authors:  Adam L Halberstadt; Mark A Geyer
Journal:  Curr Top Behav Neurosci       Date:  2018

8.  Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD).

Authors:  Simon D Brandt; Pierce V Kavanagh; Folker Westphal; Alexander Stratford; Simon P Elliott; Khoa Hoang; Jason Wallach; Adam L Halberstadt
Journal:  Drug Test Anal       Date:  2015-10-12       Impact factor: 3.345

9.  Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA).

Authors:  Adam L Halberstadt; Landon M Klein; Muhammad Chatha; Laura B Valenzuela; Alexander Stratford; Jason Wallach; David E Nichols; Simon D Brandt
Journal:  Psychopharmacology (Berl)       Date:  2018-10-08       Impact factor: 4.530

10.  Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species.

Authors:  Adam L Halberstadt; Muhammad Chatha; Adam K Klein; Jason Wallach; Simon D Brandt
Journal:  Neuropharmacology       Date:  2020-01-07       Impact factor: 5.273

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  5 in total

1.  Return of the lysergamides. Part VII: Analytical and behavioural characterization of 1-valeroyl-d-lysergic acid diethylamide (1V-LSD).

Authors:  Simon D Brandt; Pierce V Kavanagh; Folker Westphal; Benedikt Pulver; Kathleen Morton; Alexander Stratford; Geraldine Dowling; Adam L Halberstadt
Journal:  Drug Test Anal       Date:  2021-12-08       Impact factor: 3.234

2.  The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides.

Authors:  P Mallaroni; N L Mason; F R J Vinckenbosch; J G Ramaekers
Journal:  Psychopharmacology (Berl)       Date:  2022-04-30       Impact factor: 4.415

Review 3.  1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

Authors:  Sylvana Vilca-Melendez; Malin V Uthaug; Julian L Griffin
Journal:  Front Psychiatry       Date:  2021-12-13       Impact factor: 4.157

4.  Analytical profile of N-ethyl-N-cyclopropyl lysergamide (ECPLA), an isomer of lysergic acid 2,4-dimethylazetidide (LSZ).

Authors:  Simon D Brandt; Pierce V Kavanagh; Folker Westphal; Alexander Stratford; Simon P Elliott; Geraldine Dowling; Adam L Halberstadt
Journal:  Drug Test Anal       Date:  2020-09-17       Impact factor: 3.234

5.  Analytical profile, in vitro metabolism and behavioral properties of the lysergamide 1P-AL-LAD.

Authors:  Simon D Brandt; Pierce V Kavanagh; Folker Westphal; Benedikt Pulver; Hannes M Schwelm; Kyla Whitelock; Alexander Stratford; Volker Auwärter; Adam L Halberstadt
Journal:  Drug Test Anal       Date:  2022-05-29       Impact factor: 3.234

  5 in total

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