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

Drug Test Anal. 2020 Jun;12(6):812-826. doi: 10.1002/dta.2789. Epub 2020 Apr 20.

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.

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

MeSH terms

  • Animals
  • Behavior, Animal / drug effects
  • Chromatography, Liquid
  • Designer Drugs / chemistry
  • Designer Drugs / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Hallucinogens / blood
  • Hallucinogens / chemistry
  • Hallucinogens / pharmacology*
  • Lysergic Acid Diethylamide / analogs & derivatives*
  • Lysergic Acid Diethylamide / blood
  • Lysergic Acid Diethylamide / chemistry
  • Lysergic Acid Diethylamide / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Mice, Inbred C57BL
  • Prodrugs
  • Quinolines / blood
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Spectrophotometry, Infrared
  • Tandem Mass Spectrometry

Substances

  • Designer Drugs
  • Hallucinogens
  • N1-(cyclopropylmethanoyl)-lysergic acid diethylamide
  • Prodrugs
  • Quinolines
  • Lysergic Acid Diethylamide