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Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens.

  • Rickli A Psychopharmacology Research, Division of Clinical Pharmacology and Toxicology, Department of Biomedicine, University Hospital Basel and University of Basel, Basel, Switzerland.
  • Moning OD Psychopharmacology Research, Division of Clinical Pharmacology and Toxicology, Department of Biomedicine, University Hospital Basel and University of Basel, Basel, Switzerland.
  • Hoener MC Neuroscience Research, pRED, Roche Innovation Center Basel, F. Hoffmann-La Roche Ltd., Basel, Switzerland.
  • Liechti ME Psychopharmacology Research, Division of Clinical Pharmacology and Toxicology, Department of Biomedicine, University Hospital Basel and University of Basel, Basel, Switzerland. Electronic address: matthias.liechti@usb.ch.
  • 2016-05-25
Published in:
  • European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology. - 2016
DMT
Hallucinogens
LSD
Mescaline
Psilocybin
Tryptamines
Animals
Biogenic Monoamines
Cell Survival
HEK293 Cells
Hallucinogens
Humans
Kinetics
Ligands
Membrane Transport Modulators
Mice
Molecular Structure
NIH 3T3 Cells
Psychotropic Drugs
Radioligand Assay
Receptor, Serotonin, 5-HT2A
Receptor, Serotonin, 5-HT2B
Receptor, Serotonin, 5-HT2C
Recombinant Proteins
Serotonin 5-HT2 Receptor Agonists
Structure-Activity Relationship
Tryptamines
Vesicular Monoamine Transport Proteins
English The present study investigated interactions between the novel psychoactive tryptamines DiPT, 4-OH-DiPT, 4-OH-MET, 5-MeO-AMT, and 5-MeO-MiPT at monoamine receptors and transporters compared with the classic hallucinogens lysergic acid diethylamide (LSD), psilocin, N,N-dimethyltryptamine (DMT), and mescaline. We investigated binding affinities at human monoamine receptors and determined functional serotonin (5-hydroxytryptamine [5-HT]) 5-HT2A and 5-HT2B receptor activation. Binding at and the inhibition of human monoamine uptake transporters and transporter-mediated monoamine release were also determined. All of the novel tryptamines interacted with 5-HT2A receptors and were partial or full 5-HT2A agonists. Binding affinity to the 5-HT2A receptor was lower for all of the tryptamines, including psilocin and DMT, compared with LSD and correlated with the reported psychoactive doses in humans. Several tryptamines, including psilocin, DMT, DiPT, 4-OH-DiPT, and 4-OH-MET, interacted with the serotonin transporter and partially the norepinephrine transporter, similar to 3,4-methylenedioxymethamphetamine but in contrast to LSD and mescaline. LSD but not the tryptamines interacted with adrenergic and dopaminergic receptors. In conclusion, the receptor interaction profiles of the tryptamines predict hallucinogenic effects that are similar to classic serotonergic hallucinogens but also MDMA-like psychoactive properties.
Language
  • English
Open access status
green
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Persistent URL
https://sonar.ch/global/documents/18182
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