Fluorine in psychedelic phenethylamines
Drug Testing and Analysis February 28, 2012 DOI: 10.1002/dta.413 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Review Peer reviewed |
|---|---|
| Topics | Mescaline |
| Keywords | Phenethylamines Designer drug Pharmacology Potency Amphetamine Hallucinogen |
| Citations | 32 |
| Key findings | Fluorination of phenethylamines can greatly alter psychoactivity, with effects ranging from loss to enhancement and prolongation, as seen in comparisons of fluorinated escaline and mescaline analogues. |
Abstract
The so‐called psychedelic phenethylamines represent a class of drugs with a large range of psychoactive properties in humans, ranging from naturally occurring mescaline to amphetamine analogues and homologues. The interest in many of these compounds, occasionally referred to as designer‐drugs, is widely dispersed across popular culture and political and scientific communities. In recent decades, fluorine has become a powerful and important tool in medicinal chemistry. In addition, fluorine‐containing compounds and medicines can be found in numerous commercially successful pharmaceuticals that have gained a market share of some 5–15%. One might anticipate this trend to increase in the future. As far as fluorinated phenethylamines are concerned, much less is known about their chemistry and pharmacology. This paper provides an overview regarding the biological properties of over 60 fluorinated phenethylamines and discusses both historical and recent chemistry‐related developments. It was shown that the introduction of fluorine into the phenethylamine nucleus can impact greatly on psychoactivity of these compounds, ranging from marked loss to enhancement and prolongation of effects. For example, in contrast to the psychoactive escaline (70), it was observed that its fluoroescaline (76) counterpart was almost devoid of psychoactive effects. Difluoroescaline (77), on the other hand, retained, and trifluoroescaline (78) showed increased human potency of escaline (70). Difluoromescaline (72) and trifluoromescaline (73) increasingly surpassed human potency and duration of mescaline (22) effects. Copyright © 2012 John Wiley & Sons, Ltd.
Comparable studies
Other narrative reviews on mescaline, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Study of a New Schizophrenomimetic Drug—Sernyl | 1959 | Review | |
| Hallucinogens and Serotonin 5-HT2A Receptor-Mediated Signaling Pathways | 2017 | Review | |
| Hallucinogens in Mental Health: Preclinical and Clinical Studies on LSD, Psilocybin, MDMA, and Ketamine | 2020 | Review | |
| Legal highs: staying on top of the flood of novel psychoactive substances | 2015 | Review | |
| Psychedelic Drugs in Biomedicine | 2017 | Review |
Citations in the library
Cited by 11
- Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants Chemical Reviews November 30, 2023
- Monoamine receptor interaction profiles of 4-thio-substituted phenethylamines (2C-T drugs). Neuropharmacology May 15, 2018
- Olanzapine as the ideal “trip terminator”? Analysis of online reports relating to antipsychotics' use and misuse following occurrence of novel psychoactive substance‐related psychotic symptoms Human Psychopharmacology: Clinical and Experimental July 1, 2015
- Receptor Interaction Profiles of 4-Alkoxy-Substituted 2,5-Dimethoxyphenethylamines and Related Amphetamines Frontiers in Pharmacology November 28, 2019
- Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines Frontiers in Pharmacology February 9, 2022
and 6 more in the library
Cites 30
- Pilot Study of Psilocybin Treatment for Anxiety in Patients With Advanced-Stage Cancer Archives of General Psychiatry September 7, 2010
- Psychedelics and the Human Receptorome PLoS One 2010
- Which neuroreceptors mediate the subjective effects of MDMA in humans? A summary of mechanistic studies Human Psychopharmacology: Clinical and Experimental December 1, 2001
- Derivatives of 1-(1,3-benzodioxol-5-yl)-2-butanamine: representatives of a novel therapeutic class Journal of Medicinal Chemistry October 1, 1986
- The Norepinephrine Transporter Inhibitor Reboxetine Reduces Stimulant Effects of MDMA (“Ecstasy”) in Humans Clinical Pharmacology & Therapeutics June 15, 2011
and 25 more in the library