The molecular structure of psilocybin is C12H17N2O4P and its chemical name is [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate.
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What is Psilocybin?
Psilocybin is a tryptamine that occurs naturally in almost 300 species of mushrooms around the world (Rush et al., 2022).
Psilocybin’s molecular structure bears similarities to serotonin which is also a tryptamine (Hasler et al., 1997; Horita & Weber, 1961).
What is Psilocybin?
Although psilocybin is widely referred to as a psychedelic substance, it is in fact the metabolite, psilocin, that produces the psychedelic effects. Psilocybin is broken down to create psilocin in human intestinal mucosa (Horita, 1963). As a result, psilocybin is considered a prodrug.
Molecular Structure of Psilocybin
It is important to note that, in psilocybin-assisted therapy, doses of pure psilocybin are typically given, not the actual mushroom. The exact content of psilocybin in mushrooms varies based on species, growth conditions, part of the organism being used, and other variables (Andersson et al., 2008; Kamata et al., 2005; Stríbrný et al., 2003; van Amsterdam et al., 2011). As a result, synthetic psilocybin can be more accurately dosed within a Western Scientific context.
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Did You Know?
As with all living organisms, Psilocybe and other psilocybin-containing mushrooms contain many other substances in addition to psilocybin and its related compounds. Unsurprisingly, genetic research has displayed that we indeed know startling little about the metabolism of other substances in these mushrooms (Dörner et al., 2022). Some Psilocybe species, for example, also produce b-carbolines that work as MAOIs, thus blocking the degradation of psilocybin and related substances in the human digestive system (Blei et al., 2018; Lenz et al., 2020). As such, these, as well as other psychoactive and non-psychoactive components in the mushrooms, may play a crucial role in the mushrooms' effects, fundamentally underlining the difference between mushrooms and pure psilocybin.
An interesting area for future research will be in comparing the effects and effectiveness of full-bodied mushrooms containing psilocybin and various other constituents to pure psilocybin.
References
Andersson, C., Kristinsson, J., & Gry, J. (2008). Occurrence and Use of Hallucinogenic Mushrooms Containing Psilocybin Alkaloids. Nordic Council of Ministers.
Blei, F., Baldeweg, F., Fricke, J., & Hoffmeister, D. (2018). Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions. Chemistry. https://doi.org/10.1002/chem.201801047
Dörner, S., Rogge, K., Fricke, J., Schäfer, T., Wurlitzer, J. M., Gressler, M., . . . Hoffmeister, D. (2022). Genetic survey of Psilocybe natural products. Chembiochem. https://doi.org/10.1002/cbic.202200249
Hasler, F., Bourquin, D., Brenneisen, R., Bär, T., & Vollenweider, F. X. (1997). Determination of psilocin and 4-hydroxyindole-3-acetic acid in plasma by HPLC-ECD and pharmacokinetic profiles of oral and intravenous psilocybin in man. Pharm Acta Helv, 72(3), 175-184. https://doi.org/10.1016/s0031-6865(97)00014-9
Horita, A. (1963). Some biochemical studies on psilocybin and psilogin. J Neuropsychiatr, 4, 270-273.
Horita, A., & Weber, L. J. (1961). Dephosphorylation of psilocybin to psilocin by alkaline phosphatase. Proc Soc Exp Biol Med, 106, 32-34. https://doi.org/10.3181/00379727-106-26228
Kamata, T., Nishikawa, M., Katagi, M., & Tsuchihashi, H. (2005). Liquid chromatography-mass spectrometric and liquid chromatography-tandem mass spectrometric determination of hallucinogenic indoles psilocin and psilocybin in "magic mushroom" samples. J Forensic Sci, 50(2), 336-340.
Lenz, C., Wick, J., Braga, D., García-Altares, M., Lackner, G., Hertweck, C., . . . Hoffmeister, D. (2020). Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms. Angew Chem Int Ed Engl, 59(4), 1450-1454. https://doi.org/10.1002/anie.201910175
PubChem (N.d.). Psilocin. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/4980
PubChem (N.d.). Psilocybin. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/10624
Rush, B., Marcus, O., Shore, R., Cunningham, L., Thomson, N., and Rideout, K. (2022). Psychedelic Medicine: A Rapid Review of Therapeutic Applications and Implications for Future Research. Homewood Research Institute. https://hriresearch.com/research/exploratory- research/research-reports/
Stríbrný, J., Borovicka, J., & Sokol, M. (2003). [Levels of psilocybin and psilocin in various types of mushrooms]. Soud Lek, 48(3), 45-49.
van Amsterdam, J., Opperhuizen, A., & van den Brink, W. (2011). Harm potential of magic mushroom use: a review. Regul Toxicol Pharmacol, 59(3), 423-429. https://doi.org/10.1016/j.yrtph.2011.01.006