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Natural sources of drugs of abuse: magic mushrooms
... Psilocybin is an alkaloid zwitterion containing a positively charged amine group and a negatively charged phosphate 111 , which makes it more soluble in water but reduces its ability to penetrate cell membranes and the blood-brain barrier 111 . Psilocybin is rapidly dephosphorylated into psilocin by alkaline phosphatases and non-specific esterases 112 . ...
... Psilocybin is an alkaloid zwitterion containing a positively charged amine group and a negatively charged phosphate 111 , which makes it more soluble in water but reduces its ability to penetrate cell membranes and the blood-brain barrier 111 . Psilocybin is rapidly dephosphorylated into psilocin by alkaline phosphatases and non-specific esterases 112 . ...
Psilocybin therapy has recently emerged as a promising new treatment for depression and other mental health disorders. This chapter summarizes the most recent data on its safety and efficacy. The delivery of psilocybin therapy and its subjective effects are also presented. Furthermore, this chapter outlines our current understanding of psilocybin’s pharmacology and neurobiological effects. Other similar psychedelic substances with encouraging therapeutic potential are briefly presented.
... The pharmacokinetically relevant physicochemical properties of both chemicals were summarized in Supplement Table 1S. Psilocybin is soluble in water, whereas psilocin is more lipid-soluble (Ballesteros et al. 2006). Both are moderately soluble in ethanol and methanol (Ballesteros 2006). ...
... Psilocybin is soluble in water, whereas psilocin is more lipid-soluble (Ballesteros et al. 2006). Both are moderately soluble in ethanol and methanol (Ballesteros 2006). According to Lipinski's rule of 5 (Lipinski et al. 2001), both psilocybin and psilocin are likely to be well absorbed in the GI tract. ...
... Psilocybin has a water solubility of 2.7 g/L and a melting point of 224 • C. Psilocin has a water solubility of 4.08 g/L and a melting point of 174.5 • C [23]. Psilocybin is a zwitterion alkaloid with a highly polar phosphate group; consequently, it is more soluble in water than psilocin [24]. Contrariwise, psilocin is more lipid soluble than psilocybin. ...
... Both substances are soluble in methanol and ethanol but almost insoluble in ether, chloroform, and petroleum. In pure form, psilocybin and psilocin are white crystalline powders, unstable in light but relatively stable under an inert atmosphere, in the dark, and at low temperatures [23,24]. ...
Psychedelics extracted from plants have been used in religious, spiritual, and mystic practices for millennia. In 1957, Dr. Hofmann identified and synthesized the prodrug psilocybin, a substance present in more than 200 species of psychedelic mushrooms. Although there were limitations related to the scientific design of many studies, clinical observations performed during the 1950s and 1960s showed a potential therapeutic effect of psilocybin for patients affected by depressive symptoms, anxiety, and conversion disorder. Psilocybin was classed as a schedule I substance in 1970, but the fascination with psychedelics has remained almost unchanged over time, promoting a new scientific interest starting in the 1990s. Recent studies have provided further evidence supporting the suggestive hypothesis of the therapeutic use of psilocybin for treating various psychiatric disorders, including pathological anxiety, mood depressive disorder, and addiction.
... Notably, psilocybin, being a zwitterionic alkaloid and containing a highly polar phosphate group, exhibits higher solubility in water compared to psilocin. Both compounds have moderate solubility in ethanol and methanol [46]. Hence, psilocin demonstrates enhanced absorption within the rat jejunum and colon gastrointestinal tract, indicating greater bioavailability within the central nervous system [47]. ...
Depression, a global health concern with significant implications for suicide rates, remains challenging to treat effectively with conventional pharmacological options. The existing pharmaceutical interventions for these illnesses need daily dosing, are accompanied by various adverse effects, and may exhibit limited efficacy in certain cases. However, hope emerges from an unlikely source—Psilocybin, a natural hallucinogen found in certain mushrooms. Recently, this enigmatic compound has garnered attention for its potential therapeutic benefits in addressing various mental health issues, including depression. Psilocybin alters mood, cognition, and perception by acting on a particular subtype of serotonin receptors in the brain. It’s feasible that these shifts in consciousness will promote healing development, offering a novel approach to depression management. This comprehensive review explores psilocybin, derived from specific mushrooms, and its implications in the treatment of depression. The study examines new perspectives and therapeutic possibilities surrounding psilocybin, addressing existing gaps in academic literature. It delves into its biosynthesis, unique mechanisms of action, therapeutic applications, and anti-depressive effects. By uncovering the potential of this mind-altering substance, the review aims to advance psychiatric care, offering hope to those globally affected by depression.
Graphical Abstract
... Psilocybin and psilocin in their pure forms are white crystalline powders. While psilocybin is soluble in water, psilocin on the other hand is more lipid-soluble (Ballesteros et al., 2006). However, psilocin can be also diluted in an acidified aqueous solution and in dimethylsulfoxide (DMSO; up to 100 mM). ...
Psilocybin, a psychoactive alkaloid contained in hallucinogenic mushrooms, is nowadays given a lot of attention in the scientific community as a research tool for modeling psychosis as well as due to its potential therapeutic effects. However, it is also a very popular and frequently abused natural hallucinogen. This review summarizes all the past and recent knowledge on psilocybin. It briefly deals with its history, discusses the pharmacokinetics and pharmacodynamics, and compares its action in humans and animals. It attempts to describe the mechanism of psychedelic effects and objectify its action using modern imaging and psychometric methods. Finally, it describes its therapeutic and abuse potential.
Psychedelic compounds have shown extraordinary potential in treating a wide range of neuropsychiatric disorders. Psilocybin, for example, has now been shown in several clinical trials to induce a rapid (within days) and persistent (3-12 months) improvement in human major depressive disorder, treatment-resistant depression, and other neuropsychiatric conditions. Here we review the preclinical models and experimental approaches that have been used to study the neurobiological actions of psychedelic drugs. We further summarize the insights these studies have provided into the possible mechanisms underlying the induction of these therapeutic actions, including the receptors to which psychedelics bind and the second messenger signaling cascades that they activate. We also discuss potential biological processes that psychedelics may alter to produce the lasting amelioration of symptoms, including improvements in synaptic structure and function and suppression of inflammation. Improved mechanistic understanding of psychedelic drug actions will aid in the advancement of these promising new medicines.
Psilocybin and psilocin are controlled substances in many countries. These are the two main hallucinogenic compounds of the "magic mushrooms" and both act as agonists or partial agonists at 5-hydroxytryptamine (5-HT)2A subtype receptors. During the last few years, psilocybin and psilocin have gained therapeutic relevance but considerable physiological variability between individuals that can influence dose-response and toxicological profile has been reported. This review aims to discuss metabolism of psilocybin and psilocin, by presenting all major and minor psychoactive metabolites. Psilocybin is primarily a pro-drug that is dephosphorylated by alkaline phosphatase to active metabolite psilocin. This last is then further metabolized, psilocin-O-glucuronide being the main urinary metabolite with clinical and forensic relevance in diagnosis.
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