Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD).

Animals Behavior, Animal / drug effects Binding, Competitive / drug effects Biotransformation Calcium Signaling / drug effects Drug Evaluation, Preclinical Hallucinogens / pharmacokinetics Lysergic Acid Diethylamide / analogs & derivatives Male Mice Mice, Inbred C57BL Prodrugs / chemical synthesis Rats Rats, Sprague-Dawley Receptors, Serotonin, 5-HT2 / drug effects Serotonin 5-HT2 Receptor Agonists / pharmacology Serotonin 5-HT2 Receptor Antagonists / pharmacology
5-HT(2A) receptor LSD Lysergamides New psychoactive substances Psychedelics

Journal

Neuropharmacology
ISSN: 1873-7064
Titre abrégé: Neuropharmacology
Pays: England
ID NLM: 0236217

Informations de publication

Date de publication:
01 08 2020
Historique:
received: 07 07 2019
revised: 11 11 2019
accepted: 16 11 2019
pubmed: 23 11 2019
medline: 22 6 2021
entrez: 23 11 2019
Statut: ppublish

Résumé

The ergoline d-lysergic acid diethylamide (LSD) is one of the most potent psychedelic drugs. 1-Acetyl-LSD (ALD-52), a derivative of LSD containing an acetyl group on the indole nitrogen, also produces psychedelic effects in humans and has about the same potency as LSD. Recently, several other 1-acyl-substitued LSD derivatives, including 1-propanoyl-LSD (1P-LSD) and 1-butanoyl-LSD (1B-LSD), have appeared as designer drugs. Although these compounds are assumed to act as prodrugs for LSD, studies have not specifically tested this prediction. The present investigation was conducted to address the gap of information about the pharmacological effects and mechanism-of-action of 1-acyl-substituted LSD derivatives. Competitive binding studies and calcium mobilization assays were performed to assess the interaction of ALD-52, 1P-LSD, and 1B-LSD with serotonin 5-HT

Identifiants

DOI: 10.1016/j.neuropharm.2019.107856 PMID: 31756337 PMC: PMC9191647
pubmed: 31756337
pii: S0028-3908(19)30422-8
doi: 10.1016/j.neuropharm.2019.107856
pmc: PMC9191647
mid: NIHMS1802266
pii:
doi:

Substances chimiques

Hallucinogens 0
Prodrugs 0
Receptors, Serotonin, 5-HT2 0
Serotonin 5-HT2 Receptor Agonists 0
Serotonin 5-HT2 Receptor Antagonists 0
Lysergic Acid Diethylamide 8NA5SWF92O

Types de publication

Journal Article Research Support, N.I.H., Extramural Research Support, U.S. Gov't, Non-P.H.S.

Langues

eng

Sous-ensembles de citation

IM

Pagination

107856

Subventions

Organisme : NIDA NIH HHS
ID : R01 DA041336
Pays : United States
Organisme : NIMH NIH HHS
ID : HHSN271200800025C
Pays : United States

Informations de copyright

Copyright © 2019. Published by Elsevier Ltd.

Déclaration de conflit d'intérêts

Declaration of competing interest None.

Références

Biol Signals. 1994 Sep-Oct;3(5):217-22
pubmed: 7704102
Neuron. 2007 Feb 1;53(3):439-52
pubmed: 17270739
Psychopharmacology (Berl). 2019 Feb;236(2):799-808
pubmed: 30298278
J Psychopharmacol. 2019 Mar;33(3):406-414
pubmed: 30789291
Int J Legal Med. 2007 Jul;121(4):259-65
pubmed: 16496170
Eur J Clin Pharmacol. 1986;30(1):75-7
pubmed: 3709634
ACS Chem Neurosci. 2015 Jul 15;6(7):1165-75
pubmed: 25547199
J Pharmacol Exp Ther. 1993 Jun;265(3):1272-9
pubmed: 8510008
Neuropharmacology. 2014 Feb;77:200-7
pubmed: 24012658
J Psychedelic Drugs. 1979 Jan-Jun;11(1-2):53-60
pubmed: 392118
J Chromatogr B Biomed Sci Appl. 1999 Mar 5;724(1):23-33
pubmed: 10202954
Curr Top Behav Neurosci. 2018;36:159-199
pubmed: 28224459
Behav Brain Res. 2015 Jan 15;277:99-120
pubmed: 25036425
Drug Test Anal. 2019 Aug;11(8):1122-1133
pubmed: 31083768
Cell. 2017 Jan 26;168(3):377-389.e12
pubmed: 28129538
Mol Pharmacol. 1992 Nov;42(5):826-30
pubmed: 1359397
Cephalalgia. 1986 Mar;6(1):35-41
pubmed: 3698092
Int J Neuropsychopharmacol. 2015 Jun 24;19(1):
pubmed: 26108222
J Pharm Biomed Anal. 2019 Sep 10;174:270-276
pubmed: 31181490
Psychiatr Q. 1960 Apr;34:333-45
pubmed: 13765819
Biochem Pharmacol. 1979 Oct 15;28(20):3093-101
pubmed: 117811
Drug Test Anal. 2017 May;9(5):788-797
pubmed: 27422082
Eur Neuropsychopharmacol. 2016 Jul;26(7):1161-75
pubmed: 27039035
J Pharm Pharmacol. 1957 Sep;9(9):569-87
pubmed: 13463749
J Neural Transm. 1984;60(3-4):225-38
pubmed: 6527137
Mol Pharmacol. 1992 Aug;42(2):328-35
pubmed: 1355262
Anal Chem. 1988 Jul 15;60(14):1420-5
pubmed: 3218752
Curr Biol. 2017 Feb 6;27(3):451-457
pubmed: 28132813
Neuropharmacology. 2019 Jan;144:368-376
pubmed: 30385253
Neuropharmacology. 2015 Dec;99:546-53
pubmed: 26318099
Anal Bioanal Chem. 2019 Jul;411(19):4751-4763
pubmed: 30617391
Front Pharmacol. 2017 Nov 08;8:814
pubmed: 29167644
Life Sci. 1974 Dec 1;15(11):1935-44
pubmed: 4620998
Pharmacol Biochem Behav. 2001 Jul-Aug;69(3-4):643-52
pubmed: 11509227
Drug Test Anal. 2016 Sep;8(9):891-902
pubmed: 26456305
J Psychopharmacol. 2011 Nov;25(11):1548-61
pubmed: 21148021
Psychopharmacology (Berl). 1998 Apr;136(4):409-14
pubmed: 9600588
Clin Pharmacol Ther. 1964 Sep-Oct;5:611-4
pubmed: 14209776
Mol Pharmacol. 2003 Dec;64(6):1295-308
pubmed: 14645659
Neuroreport. 1998 Dec 1;9(17):3897-902
pubmed: 9875725
Psychopharmacology (Berl). 2017 Jul;234(13):2031-2046
pubmed: 28386699
Synapse. 2000 Feb;35(2):144-50
pubmed: 10611640
Mol Pharmacol. 1996 Jul;50(1):34-42
pubmed: 8700116
Drug Metab Dispos. 1990 May-Jun;18(3):338-43
pubmed: 1974196
Psychol Med. 2018 Jul;48(9):1464-1473
pubmed: 28967351
J Clin Lab Anal. 2018 Feb;32(2):
pubmed: 28548305
J Anal Toxicol. 1996 Jan-Feb;20(1):27-37
pubmed: 8837948
J Psychopharmacol. 2012 Jul;26(7):994-1002
pubmed: 22406913
Biochem Pharmacol. 1979 Oct 15;28(20):3081-91
pubmed: 518707
Drug Test Anal. 2012 Jul-Aug;4(7-8):556-76
pubmed: 22517680
Elife. 2018 Oct 25;7:
pubmed: 30355445
Neuropharmacology. 2016 Aug;107:364-375
pubmed: 27020041
Ann N Y Acad Sci. 1957 Mar 14;66(3):435-44
pubmed: 13425233
Science. 2013 May 3;340(6132):615-9
pubmed: 23519215
Mol Pharmacol. 1994 Feb;45(2):277-86
pubmed: 8114677
J Anal Toxicol. 1996 Sep;20(5):323-9
pubmed: 8872243
Eur J Pharmacol. 1993 Aug 3;239(1-3):111-8
pubmed: 8223886
Forensic Sci Int. 1985 Aug;28(3-4):229-37
pubmed: 4065782
Neuropharmacology. 2018 Nov;142:231-239
pubmed: 29499272
Psychopharmacologia. 1967;11(1):65-78
pubmed: 5302272
Psychopharmacology (Berl). 2013 Jun;227(4):727-39
pubmed: 23407781
Drug Test Anal. 2017 Jan;9(1):38-50
pubmed: 27265891
J Chromatogr B Biomed Sci Appl. 2001 Dec 5;765(1):15-27
pubmed: 11817305
Transl Psychiatry. 2017 Apr 4;7(4):e1084
pubmed: 28375205
Biochem Pharmacol. 1973 Dec 1;22(23):3099-108
pubmed: 4202581
Psychopharmacologia. 1959;1:20-8
pubmed: 14405872
Biochem Soc Trans. 1975;3(2):290-2
pubmed: 1132562
Drug Test Anal. 2018 Feb;10(2):310-322
pubmed: 28585392
Neuropsychopharmacology. 2019 Jun;44(7):1328-1334
pubmed: 30685771
Anesth Analg. 1964 May-Jun;43:285-91
pubmed: 14169837
Nat Struct Mol Biol. 2018 Sep;25(9):787-796
pubmed: 30127358
J Med Chem. 2002 Sep 12;45(19):4344-9
pubmed: 12213075
J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Oct 15;825(1):21-8
pubmed: 16154519
Drug Test Anal. 2017 Oct;9(10):1641-1649
pubmed: 28342178
Biochem Pharmacol. 1974 Mar 15;23(6):1073-8
pubmed: 4151050
Cereb Cortex. 2018 Nov 1;28(11):3939-3950
pubmed: 29028939
Curr Top Behav Neurosci. 2018;36:1-43
pubmed: 28401524
Psychopharmacology (Berl). 1996 Nov;128(2):198-205
pubmed: 8956381
J Neurosci. 2018 Apr 4;38(14):3603-3611
pubmed: 29555857
Curr Psychiatr Ther. 1969;9:144-52
pubmed: 5348915
J Psychopharmacol. 2015 Jan;29(1):57-68
pubmed: 25389218

Auteurs

Adam L Halberstadt (AL)

Department of Psychiatry, University of California San Diego, La Jolla, CA, 92093-0804, USA; Research Service, VA San Diego Healthcare System, 3350 La Jolla Village Dr, San Diego, CA, 92161, USA. Electronic address: ahalberstadt@ucsd.edu.

Muhammad Chatha (M)

Department of Psychiatry, University of California San Diego, La Jolla, CA, 92093-0804, USA.

Adam K Klein (AK)

Department of Psychiatry, University of California San Diego, La Jolla, CA, 92093-0804, USA.

John D McCorvy (JD)

Department of Cell Biology, Neurobiology & Anatomy, Medical College of Wisconsin, Milwaukee, WI, USA.

Markus R Meyer (MR)

Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, Center for Molecular Signaling (PZMS), Saarland University, 66421, Homburg, Germany.

Lea Wagmann (L)

Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, Center for Molecular Signaling (PZMS), Saarland University, 66421, Homburg, Germany.

Alexander Stratford (A)

Synex Synthetics BV, Karveelweg 20, 6222NH, Maastricht, the Netherlands.

Simon D Brandt (SD)

School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool, L3 3AF, UK.

Articles similaires

Smoking Cessation and Incident Cardiovascular Disease.

Jun Hwan Cho, Seung Yong Shin, Hoseob Kim et al.
1.00
Humans Male Smoking Cessation Cardiovascular Diseases Female

Evaluation of Low-Value Services Across Major Medicare Advantage Insurers and Traditional Medicare.

Ciara Duggan, Adam L Beckman, Ishani Ganguli et al.
1.00
Humans United States Aged Cross-Sectional Studies Medicare Part C

Effectiveness of Virtual Yoga for Chronic Low Back Pain: A Randomized Clinical Trial.

Hallie Tankha, Devyn Gaskins, Amanda Shallcross et al.
1.00
Humans Yoga Low Back Pain Female Male

Meal Timing and Anthropometric and Metabolic Outcomes: A Systematic Review and Meta-Analysis.

Hiu Yee Liu, Ashley A Eso, Nathan Cook et al.
1.00
Humans Meals Time Factors Female Adult

Classifications MeSH

questionsmedicales.fr › Eucaryotes › Animaux › Pharmacological and biotransformation studies...
questionsmedicales.fr › Comportement et mécanismes comportementaux › Comportement › Comportement animal › Pharmacological and biotransformation studies...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Sites de fixation › Fixation compétitive › Pharmacological and biotransformation studies...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Pharmacocinétique › Biotransformation › Pharmacological and biotransformation studies...
questionsmedicales.fr › Phénomènes physiologiques cellulaires › Transduction du signal › Systèmes de seconds messagers › Signalisation calcique › Pharmacological and biotransformation studies...
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Pharmacological and biotransformation studies...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Agents du système nerveux central › Psychoanaleptiques › Hallucinogènes › Pharmacological and biotransformation studies...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérocycliques avec 4 noyaux ou plus › Ergolines › Acide lysergique › Lysergide › Pharmacological and biotransformation studies...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Souris › Pharmacological and biotransformation studies...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Souris › Lignées consanguines de souris › Souris de lignée C57BL › Pharmacological and biotransformation studies...
questionsmedicales.fr › Préparations pharmaceutiques › Promédicaments › Pharmacological and biotransformation studies...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Rats › Pharmacological and biotransformation studies...
questionsmedicales.fr › Eucaryotes › Animaux › Chordés › Vertébrés › Mammifères › Eutheria › Rodentia › Muridae › Murinae › Rats › Rat Sprague-Dawley › Pharmacological and biotransformation studies...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines membranaires › Récepteurs de surface cellulaire › Récepteurs aux neuromédiateurs › Récepteurs sérotoninergiques › Récepteurs de la sérotonine de type 5-HT2 › Pharmacological and biotransformation studies...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Agents neuromédiateurs › Agents sérotoninergiques › Agonistes des récepteurs de la sérotonine › Agonistes des récepteurs 5-HT2 de la sérotonine › Pharmacological and biotransformation studies...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Agents neuromédiateurs › Agents sérotoninergiques › Antisérotonines › Antagonistes des récepteurs 5-HT2 de la sérotonine › Pharmacological and biotransformation studies...