Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H16N2O |
| Molecular Weight | 204.2682 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCC1=CNC2=C1C(O)=CC=C2
InChI
InChIKey=SPCIYGNTAMCTRO-UHFFFAOYSA-N
InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25342005 | https://www.ncbi.nlm.nih.gov/pubmed/23851905 | https://www.ncbi.nlm.nih.gov/pubmed/21148021 | https://www.ncbi.nlm.nih.gov/pubmed/11101361https://www.ncbi.nlm.nih.gov/pubmed/26841800 | https://clinicaltrials.gov/ct2/show/NCT03341689 | http://onlinelibrary.wiley.com/doi/10.1002/hlca.19590420518/abstract | https://clinicaltrials.gov/ct2/show/NCT02061293 | https://clinicaltrials.gov/ct2/show/NCT03181529
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25342005 | https://www.ncbi.nlm.nih.gov/pubmed/23851905 | https://www.ncbi.nlm.nih.gov/pubmed/21148021 | https://www.ncbi.nlm.nih.gov/pubmed/11101361https://www.ncbi.nlm.nih.gov/pubmed/26841800 | https://clinicaltrials.gov/ct2/show/NCT03341689 | http://onlinelibrary.wiley.com/doi/10.1002/hlca.19590420518/abstract | https://clinicaltrials.gov/ct2/show/NCT02061293 | https://clinicaltrials.gov/ct2/show/NCT03181529
Psilocybin is a naturally occurring psychedelic prodrug compound produced by more than 200 species of mushrooms, collectively known as psilocybin mushrooms. Once ingested, psilocybin is rapidly metabolized to the psilocin, which then acts on serotonin receptors in the brain. Psilocybin was identified as the active hallucinogenic compound in magic mushrooms in 1959, but humans have used assorted psilocybin mushrooms in religious ceremonies since prehistoric times. In the 1960's psilocybin was marketed for use as a treatment for various psychoses, however, it was withdrawn from the market when the regulatory environment changed. Recently there has been as renewed interest in studying the medicinal uses of psilocybin for treatment of anxiety, depression, migraine headaches, addictions, and other neuropsychiatric conditions.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) |
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Target ID: Q64264 Gene ID: 15550.0 Gene Symbol: Htr1a Target Organism: Mus musculus (Mouse) |
49.0 nM [Ki] | ||
Target ID: P35363 Gene ID: 15558.0 Gene Symbol: Htr2a Target Organism: Mus musculus (Mouse) |
25.0 nM [Ki] | ||
Target ID: P34968 Gene ID: 15560.0 Gene Symbol: Htr2c Target Organism: Mus musculus (Mouse) |
10.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
|||
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
16 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
26 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
37.6 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
140 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
213 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
267 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.3 mg/kg single, oral dose: 0.3 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.45 mg/kg single, oral dose: 0.45 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28353056 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
PSILOCIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines. | 2000 Nov 30 |
|
| Brain mechanisms of hallucinogens and entactogens. | 2001 Dec |
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| [Hallucinogenic mushrooms]. | 2005 |
|
| [Hallucinogenic fungi (Psylocibe). Part I. Characteristics, results of consumption, recognition]. | 2005 Jul-Sep |
|
| Investigation into the temporal stability of aqueous standard solutions of psilocin and psilocybin using high performance liquid chromatography. | 2006 Apr-Jun |
|
| Psilocybin can occasion mystical-type experiences having substantial and sustained personal meaning and spiritual significance. | 2006 Aug |
|
| The determination of psilocin and psilocybin in hallucinogenic mushrooms by HPLC utilizing a dual reagent acidic potassium permanganate and tris(2,2'-bipyridyl)ruthenium(II) chemiluminescence detection system. | 2006 Jan |
|
| Psilocin identified in a DUID investigation. | 2006 Jun |
|
| Response of cluster headache to psilocybin and LSD. | 2006 Jun 27 |
|
| Safety, tolerability, and efficacy of psilocybin in 9 patients with obsessive-compulsive disorder. | 2006 Nov |
|
| Not imagining it. Research into hallucinogens cautiously resumes. | 2006 Nov |
|
| [Chronic cluster headache: Response to psilocybin]. | 2006 Nov 1-15 |
|
| Phylogenetic relationship of psychoactive fungi based on rRNA gene for a large subunit and their identification using the TaqMan assay (II). | 2006 Nov 10 |
|
| Reviving the study of hallucinogens. | 2006 Oct |
|
| Application of ion mobility spectrometry in cases of forensic interest. | 2006 Sep 12 |
|
| [Concentration of selected microelements in blood serum of rats exposed to the action of psilocin and phenylethylamine]. | 2007 |
|
| 5-Year trends in use of hallucinogens and other adjunct drugs among UK dance drug users. | 2007 |
|
| Psilocybin links binocular rivalry switch rate to attention and subjective arousal levels in humans. | 2007 Dec |
|
| [Automutilation after consumption of hallucinogenic mushrooms]. | 2007 Dec 29 |
|
| Effects of psilocybin on time perception and temporal control of behaviour in humans. | 2007 Jan |
|
| [Hallucinogenic fungi (psilocybe). Part II. Identification of Psilocybe semilanceata by PCR]. | 2007 Jul-Sep |
|
| [Prof. Günther Hole on his self-experiments. "What did I actually endure?"]. | 2007 Mar 15 |
|
| Psilocybin-induced stimulus control in the rat. | 2007 Oct |
|
| The effects of the preferential 5-HT2A agonist psilocybin on prepulse inhibition of startle in healthy human volunteers depend on interstimulus interval. | 2007 Sep |
|
| Albert Hofmann, the father of LSD (1906-2008). | 2008 |
|
| Between prohibitions: patterns and meanings of magic mushroom use in the UK. | 2008 |
|
| Effects of varied doses of psilocybin on time interval reproduction in human subjects. | 2008 Apr 11 |
|
| Mystical-type experiences occasioned by psilocybin mediate the attribution of personal meaning and spiritual significance 14 months later. | 2008 Aug |
|
| The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists. | 2008 Aug |
|
| Hallucinogen-like effects of N,N-dipropyltryptamine (DPT): possible mediation by serotonin 5-HT1A and 5-HT2A receptors in rodents. | 2008 Jan |
|
| [Hallucinogen-induced psychological disorders]. | 2008 Jun |
|
| Unrecognized magic mushroom abuse in a 28-year-old man. | 2008 Oct |
|
| Analysis of mushroom exposures in Texas requiring hospitalization, 2005-2006. | 2009 Jun |
|
| Apical regional wall motion abnormalities reminiscent to Tako-Tsubo cardiomyopathy following consumption of psychoactive fungi. | 2009 May 1 |
|
| Return of a problem child. | 2009 Oct |
|
| Unifying electron transfer mechanism for psilocybin and psilocin. | 2009 Oct |
|
| Availability of websites offering to sell psilocybin spores and psilocybin. | 2009 Sep |
|
| Sensorimotor gating depends on polymorphisms of the serotonin-2A receptor and catechol-O-methyltransferase, but not on neuregulin-1 Arg38Gln genotype: a replication study. | 2009 Sep 15 |
|
| Micro-solid phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry for the determination of stimulants, hallucinogens, ketamine and phencyclidine in oral fluids. | 2010 Aug 24 |
|
| Psychometric evaluation of the altered states of consciousness rating scale (OAV). | 2010 Aug 31 |
|
| Hallucinogens as medicine. | 2010 Dec |
|
| Forensic analysis of hallucinogenic mushrooms and khat (Catha edulis Forsk) using cation-exchange liquid chromatography. | 2010 Feb 25 |
|
| Comparative study of ATR and transflection IR spectroscopic techniques for the analysis of hallucinogenic mushrooms. | 2010 Feb 25 |
|
| Glucuronidation of psilocin and 4-hydroxyindole by the human UDP-glucuronosyltransferases. | 2010 Mar |
|
| Timothy Leary, Richard Alpert (Ram Dass) and the changing definition of psilocybin. | 2010 May |
|
| Turn on, tune in, but don't drop out: The impact of neo-liberalism on magic mushroom users' (in)ability to imagine collectivist social worlds. | 2010 Nov |
|
| Differential contributions of serotonin receptors to the behavioral effects of indoleamine hallucinogens in mice. | 2011 Nov |
|
| Fungal hallucinogens psilocin, ibotenic acid, and muscimol: analytical methods and biologic activities. | 2013 Aug |
|
| Effect of psilocin on extracellular dopamine and serotonin levels in the mesoaccumbens and mesocortical pathway in awake rats. | 2015 |
|
| The hallucinogenic world of tryptamines: an updated review. | 2015 Aug |
Sample Use Guides
Rats were administered 5 and 10 mg/kg of Psilocin as an intraperitoneal injection. Following the dosing protocol, extracellular dopamine levels were increased in the nucleus accumbens. Psilocin did not affect the extracellular 5-HT level in the nucleus accumbens. However, systemic administration of 10 mg/kg of psilocin significantly increased extracellular 5-HT levels in the ventral tegmental area, but decreased dopamine in this area. Behaviorally, psilocin significantly increased the number of head twitches.
Route of Administration:
Intraperitoneal
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| Classification Tree | Code System | Code | ||
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DEA NO. |
7438
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WIKIPEDIA |
TiHKAL
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208-296-5
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100000085668
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8613
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SUB22051
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PSILOCIN
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CMS88KUW0G
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520-53-6
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4980
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DTXSID5048899
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m9304
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C009105
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
