Return of the lysergamides. Part III: Analytical characterization of N6-ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD).
The psychoactive properties of lysergic acid diethylamide (LSD) have fascinated scientists across disciplines and the exploration of other analogues and derivatives has been motivated by deepening the understanding of ligand-receptor interactions at the molecular level as well as by the search for new therapeutics. Several LSD congeners have appeared on the new psychoactive substances (NPS) market in the form of blotters or powders. Examples include 1-propionyl-LSD (1P-LSD), AL-LAD, and LSZ. The absence of analytical data for novel compounds is a frequent challenge encountered in clinical and toxicological investigations. Two newly emerging lysergamides, namely N6-ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1P-ETH-LAD, were characterized by gas chromatography-mass spectrometry (GC-MS), low and high mass accuracy electrospray MS(/MS), GC solid-state infrared analysis, high performance liquid chromatography diode array detection as well as nuclear magnetic resonance spectroscopy. Limited analytical data for ETH-LAD were previously available, whereas information about 1P-ETH-LAD has not previously been encountered in the scientific literature. This study extends the characterization of lysergamides distributed on the NPS market, which will help to make analytical data available to clinicians, toxicologists, and other stakeholders who are likely to encounter these substances. The analysis of a test incubation of 1P-ETH-LAD with human serum at 37°C by LC single quadrupole MS at various time points (0-6 h, once per hour and one measurement after 24 h) revealed the formation of ETH-LAD, suggesting that 1P-ETH-LAD might serve as a pro-drug. 1P-ETH-LAD was still detectable in serum after 24 h. Copyright © 2017 John Wiley & Sons, Ltd.
School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.
Simon D
http://orcid.org/0000-0001-8632-5372
SD
Brandt
Department of Pharmacology and Therapeutics, School of Medicine, Trinity Centre for Health Sciences, St James's Hospital, Dublin 8, D08W9RT, Ireland.
Pierce V
PV
Kavanagh
State Bureau of Criminal Investigation Schleswig-Holstein, Section Narcotics/Toxicology, Mühlenweg 166, D-24116, Kiel, Germany.
Folker
F
Westphal
Alere Forensics (Forensics Ltd), Malvern Hills Science Park, Geraldine Road, WR14 3SZ, UK.
Simon P
SP
Elliott
Department of Pharmaceutical Sciences, Philadelphia College of Pharmacy, University of the Sciences, 600 South 43rd Street, Philadelphia, PA, 19104, USA.
Jason
J
Wallach
Synex Synthetics BV, Poortweg 4, 2612 PA, Delft, the Netherlands.
Alexander
A
Stratford
Division of Chemical Biology and Medicinal Chemistry, University of North Carolina, Genetic Medicine Building, 120 Mason Farm Road, Chapel Hill, NC, 27599, USA.
David E
DE
Nichols
Department of Psychiatry, University of California San Diego, 9500 Gilman Drive, La Jolla, CA, 92093-0804, USA.
Adam L
AL
Halberstadt
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D015198:Designer Drugs / Q000032:analysis* / Q000493:pharmacokinetics; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods; D006801:Humans; D008238:Lysergic Acid Diethylamide / Q000031:analogs & derivatives* / Q000032:analysis / Q000097:blood; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D011619:Psychotropic Drugs / Q000032:analysis* / Q000097:blood; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D015813:Substance Abuse Detection / Q000379:methods
D015198:Designer Drugs; D011619:Psychotropic Drugs; C016543:lysergamide; D008238:Lysergic Acid Diethylamide
LSD; chemical analysis; lysergamides; new psychoactive substances; psychedelics