Analytical and behavioral characterization of 1-hexanoyl-LSD (1H-LSD).
LSD
head‐twitch response
new psychoactive substances
psychedelics
Journal
Drug testing and analysis
ISSN: 1942-7611
Titre abrégé: Drug Test Anal
Pays: England
ID NLM: 101483449
Informations de publication
Date de publication:
04 Jul 2024
04 Jul 2024
Historique:
revised:
24
06
2024
received:
01
06
2024
accepted:
25
06
2024
medline:
5
7
2024
pubmed:
5
7
2024
entrez:
5
7
2024
Statut:
aheadofprint
Résumé
The development of lysergic acid diethylamide (LSD) derivatives and analogs continues to inform the design of novel receptor probes and potentially new medicines. On the other hand, a number of newly developed LSD derivatives have also emerged as recreational drugs, leading to reports of their detection in some countries. One position in the ergoline scaffold of LSD that is frequently targeted is the N
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Veteran's Administration VISN 22 Mental Illness Research, Education, and Clinical Center (MIRECC)
Informations de copyright
© 2024 The Author(s). Drug Testing and Analysis published by John Wiley & Sons Ltd.
Références
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). EMCDDA‐Europol 2015 Annual report on the implementation of Council Decision 2005/387/JHA. EMCDDA, 2016. Available at: http://www.emcdda.europa.eu/system/files/publications/2880/TDAS16001ENN.pdf [Accessed 21 January 2024].
Brandt SD, Kavanagh PV, Westphal F, et al. Return of the lysergamides. Part I: analytical and behavioural characterization of 1‐propionyl‐d‐lysergic acid diethylamide (1P‐LSD). Drug Test Anal. 2016;8(9):891‐902. doi:10.1002/dta.1884
Troxler F, Hofmann A. Substitutionen am Ringsystem der Lysergsäure I. Substitutionen am Indol‐Stickstoff. 43. Mitteilung über Mutterkornalkaloide. Helv Chim Acta. 1957;40(6):1706‐1720. doi:10.1002/hlca.19570400619
European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). EMCDDA‐Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA. EMCDDA, 2017. Available at: http://www.emcdda.europa.eu/system/files/publications/4724/TDAN17001ENN_PDFWEB.pdf [21 January 2024].
Halberstadt AL, Klein LM, Chatha M, et al. Pharmacological characterization of the LSD analog N‐ethyl‐N‐cyclopropyl lysergamide (ECPLA). Psychopharmacology (Berl). 2019;236(2):799‐808. doi:10.1007/s00213‐018‐5055‐9
Halberstadt AL, Chatha M, Klein AK, et al. Pharmacological and biotransformation studies of 1‐acyl‐substituted derivatives of d‐lysergic acid diethylamide (LSD). Neuropharmacology. 2020;172:107856. doi:10.1016/j.neuropharm.2019.107856
Wagmann L, Richter LHJ, Kehl T, et al. In vitro metabolic fate of nine LSD‐based new psychoactive substances and their analytical detectability in different urinary screening procedures. Anal Bioanal Chem. 2019;411(19):4751‐4763. doi:10.1007/s00216‐018‐1558‐9
Grumann C, Henkel K, Stratford A, et al. Validation of an LC‐MS/MS method for the quantitative analysis of 1P‐LSD and its tentative metabolite LSD in fortified urine and serum samples including stability tests for 1P‐LSD under different storage conditions. J Pharm Biomed Anal. 2019;174:270‐276. doi:10.1016/j.jpba.2019.05.062
Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter V. Pharmacokinetics and subjective effects of 1P‐LSD in humans after oral and intravenous administration. Drug Test Anal. 2020;12(8):1144‐1153. doi:10.1002/dta.2821
Stratford A, Williamson JPB. Prodrugs of substituted ergolines. WO2024/028495A1. Synex Holdings BV; 2024.
Brandt SD, Kavanagh PV, Westphal F, et al. Return of the lysergamides. Part V: analytical and behavioural characterization of 1‐butanoyl‐d‐lysergic acid diethylamide (1B‐LSD). Drug Test Anal. 2019;11(8):1122‐1133. doi:10.1002/dta.2613
Tanaka R, Kawamura M, Hakamatsuka T, Kikura‐Hanajiri R. Identification of LSD derivatives, 1cP‐LSD, MIPLA and 1B‐LSD in illegal products as paper sheet. Yakugaku Zasshi. 2020;140(11):1405‐1413. doi:10.1248/yakushi.20‐00124
Tsochatzis E, Lopes AJ, Reniero F, Holland M, Åberg J, Guillou C. Identification of 1‐butyl‐lysergic acid diethylamide (1B‐LSD) in seized blotter paper using an integrated workflow of analytical techniques and chemo‐informatics. Molecules. 2020;25(3):E712. doi:10.3390/molecules25030712
Brandt SD, Kavanagh PV, Westphal F, et al. Return of the lysergamides. Part VII: analytical and behavioural characterization of 1‐valeroyl‐d‐lysergic acid diethylamide (1V‐LSD). Drug Test Anal. 2022;14(4):733‐740. doi:10.1002/dta.3205
Tanaka R, Kawamura M, Mizutani S, Kikura‐Hanajiri R. Identification of LSD analogs, 1cP‐AL‐LAD, 1cP‐MIPLA, 1V‐LSD and LSZ in sheet products. Forensic Toxicol. 2023;41(2):294‐303. doi:10.1007/s11419‐023‐00661‐1
Kavanagh PV, Westphal F, Pulver B, et al. Analytical and behavioral characterization of 1‐dodecanoyl‐LSD (1DD‐LSD). Drug Test Anal. 2024. doi:10.1002/dta.3691
Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD. Correlation between the potency of hallucinogens in the mouse head‐twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology. 2020;167:107933. doi:10.1016/j.neuropharm.2019.107933
Canal CE, Morgan D. Head‐twitch response in rodents induced by the hallucinogen 2,5‐dimethoxy‐4‐iodoamphetamine: a comprehensive history, a re‐evaluation of mechanisms, and its utility as a model. Drug Test Anal. 2012;4(7–8):556‐576. doi:10.1002/dta.1333
Halberstadt AL, Geyer MA. Effect of hallucinogens on unconditioned behavior. Curr Top Behav Neurosci. 2018;36:159‐199. doi:10.1007/7854_2016_466
Halberstadt AL, Geyer MA. Characterization of the head‐twitch response induced by hallucinogens in mice: detection of the behavior based on the dynamics of head movement. Psychopharmacology (Berl). 2013;227(4):727‐739. doi:10.1007/s00213‐013‐3006‐z
Halberstadt AL. Automated detection of the head‐twitch response using wavelet scalograms and a deep convolutional neural network. Sci Rep. 2020;10(1):8344. doi:10.1038/s41598‐020‐65264‐x
Fantegrossi WE, Simoneau J, Cohen MS, et al. Interaction of 5‐HT2A and 5‐HT2C receptors in R(−)‐2,5‐dimethoxy‐4‐iodoamphetamine‐elicited head twitch behavior in mice. J Pharmacol Exp Ther. 2010;335(3):728‐734. doi:10.1124/jpet.110.172247
Brandt SD, Kavanagh PV, Westphal F, et al. Return of the lysergamides. Part VI: analytical and behavioural characterization of 1‐cyclopropanoyl‐d‐lysergic acid diethylamide (1CP‐LSD). Drug Test Anal. 2020;12(6):812‐826. doi:10.1002/dta.2789