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Pronunciation | /ˌsaɪləˈsaɪbɪn/ sy-lə-SY-bin, /ˌsɪl-/ |
Other names | Psilocybine; Psilocibin; Psylocybin; Psilocybinum; Psilotsibin; Psilocin phosphate; Psilocin phosphate ester; Indocybin; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine; 4-Phosphoryloxy-N,N-dimethyltryptamine; 4-Phosphoryl-N,N-dimethyltryptamine; 4-PO-DMT; 4-PO-N,N-DMT; COMP-360; COMP360, Psilocybin (USAN US) |
Dependence liability | Low[1][2][3][4][5] |
Addiction liability | Low[1][6] |
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Drug class | Serotonergic psychedelic (hallucinogen)[8] |
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Pharmacokinetic data | |
Bioavailability | Oral: 52.7 ± 20.4% (as psilocin) (n=3)[10][11][12] |
Protein binding | 66%[13] |
Metabolism | Liver, other tissues:[11][10][7][16] • Dephosphorylation (ALP ) • Demethylation and deamination (MAO ) • Oxidation (ALDH ) • Glucuronidation (UGTs) |
Metabolites | • Psilocin[11][10][7] • Psilocin-O-glucuronide[10][7] • 4-Hydroxyindole-3-acetaldehyde[10][7] • 4-Hydroxyindole-3-acetic acid (4-HIAA)[10][7] • 4-Hydroxytryptophol[10][7] |
Onset of action | Oral: 20–40 min[11] |
Elimination half-life | Oral (as psilocin): 2.1–3.7 hours (range 1.5–18.6 hours)[10] IV (as psilocin): 1.2 hours (range 1.8–4.5 hours)[10][2] |
Duration of action | Oral: 4–6 hours (range 3–12 hours)[11][14] IV : 15–30 minutes (1 mg, n=6)[2][12] |
Excretion | Urine (mainly as psilocin-O-glucuronide, 2–4% as unchanged psilocin)[10][7][15] |
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ECHA InfoCard | 100.007.542 |
Chemical and physical data | |
Formula | C12H17N2O4P |
Molar mass | 284.252 g·mol−1 |
3D model (JSmol) | |
Melting point | 220–228 °C (428–442 °F) [17] |
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Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), and formerly sold under the brand name Indocybin,[a] is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of other classical psychedelics. Effects include euphoria, hallucinations, changes in perception, a distorted sense of time,[19] and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.
Imagery in cave paintings and rock art of modern-day Algeria and Spain suggests that human use of psilocybin mushrooms predates recorded history.[20] In Mesoamerica, the mushrooms had long been consumed in spiritual and divinatory ceremonies before Spanish chroniclers first documented their use in the 16th century. In 1958, the Swiss chemist Albert Hofmann isolated psilocybin and psilocin from the mushroom Psilocybe mexicana. His employer, Sandoz, marketed and sold pure psilocybin to physicians and clinicians worldwide for use in psychedelic therapy. Increasingly restrictive drug laws of the 1960s and the 1970s curbed scientific research into the effects of psilocybin and other hallucinogens, but its popularity as an entheogen (spirituality-enhancing agent) grew in the next decade, owing largely to the increased availability of information on how to cultivate psilocybin mushrooms.
The intensity and duration of psilocybin's effects vary, depending on species or cultivar of mushrooms, dosage, individual physiology, and set and setting, as shown in experiments led by Timothy Leary at Harvard University in the early 1960s. Once ingested, psilocybin is rapidly metabolized to psilocin, which then acts on serotonin receptors in the brain. Psilocybin's mind-altering effects typically last two to six hours, although to people under the influence of psilocybin, they may seem to last much longer, since the drug can distort the perception of time. Possession of psilocybin-containing mushrooms has been outlawed in most countries, and psilocybin has been classified as a Schedule I controlled substance under the 1971 United Nations Convention on Psychotropic Substances.
Passie2002
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was invoked but never defined (see the help page).With a logS value of −3.009 and a plasma protein binding of 0.66, respectively, psilocybin has poor water solubility and is moderately bound to plasma proteins.
When selecting adverse event profile rates, the shortest time period available was selected and analyzed (eg, day 1 instead of day 30) since the half-life of psilocin is 3 ± 1.1 hours when taken orally and the duration of action can range between 3 to 12 hours.12,13
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