NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
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IUPAC Traditional name
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Synonyms
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Psilocybin
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3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester
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4-Phosphoryl-N,N-dimethyltryptamine
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Cy 39
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Indocybin
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Psilocybine
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O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine
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Psilocine Phosphate
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3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl phosphate
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Psilocybin
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CAS Number
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EC Number
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MDL Number
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Beilstein Number
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PubChem SID
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PubChem CID
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CHEBI ID
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CHEMBL
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Chemspider ID
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KEGG ID
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MeSH Name
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Wikipedia Title
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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1.7443777
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H Acceptors
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4
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H Donor
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3
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LogD (pH = 5.5)
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-0.15883611
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LogD (pH = 7.4)
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-0.89353734
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Log P
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-0.13636683
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Molar Refractivity
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73.296 cm3
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Polarizability
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29.192675 Å3
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Polar Surface Area
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85.79 Å2
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Rotatable Bonds
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5
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Lipinski's Rule of Five
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true
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PROPERTIES
PROPERTIES
Physical Property
Safety Information
Pharmacology Properties
Product Information
Bioassay(PubChem)
Solubility
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H2O: >20 mg/mL
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Methanol (Hot),
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soluble in methanol slightly soluble in ethanol negligible in chloroform, benzene
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soluble in water
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Water
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Apperance
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solid
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White to Off-White Solid
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Melting Point
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226-2280C
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Storage Condition
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Controlled Substance, -20°C Freezer
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RTECS
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NM3150000
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MSDS Link
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German water hazard class
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3
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LD50
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285 mg/kg (mouse, i.v.) 280 mg/kg (rat, i.v.) 12.5 mg/kg (rabbit, i.v.)
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Personal Protective Equipment
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Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
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Drug Control
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USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada
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Storage Temperature
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-20°C
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Admin Routes
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Oral, intravenous
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Dependency Liability
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Low
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Excretion
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Renal
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Half Life
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oral: 163±64 min intravenous: 74.1±19.6 min
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Metabolism
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Hepatic
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Legal Status
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Class A (UK)
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S9 (Australia)
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Schedule I (US)
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Schedule III (Canada)
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Purity
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≥98% (HPLC)
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Certificate of Analysis
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Empirical Formula (Hill Notation)
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C12H17N2O4P
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DETAILS
DETAILS
Wikipedia
Sigma Aldrich
TRC
Sigma Aldrich -
P0100
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Biochem/physiol Actions Psilocybin is a hallucinogenic serotonin 1A and 2A agonist and psychotomimetic. It is the minor hallucinogenic component of Teonanácatl, the sacred mushroom of Mexico. Psilocybin produces muscle relaxation, dilation of pupils, vivid visual and auditory distortions, and emotional disturbances. |
Toronto Research Chemicals -
P839650
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The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being Psilocin. Psychomimetic.Controlled substance (hallucinogen). |
REFERENCES
REFERENCES
From Suppliers
Google Scholar
PubMed
Google Books
- • Hofmann, et al.: Experientia, 14, 397 (1958)
- • Callahan, P., et al.: J. Pharmacol. Exp. Ther., 246, 866 (1958)
- • Appel, J., et al.: Eur. J. Pharmacol., 159, 41 (1958)
- • Blair, J., et al.: J. Med. Chem., 43, 4701 (1958)
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PATENTS
PATENTS
PubChem Patent
Google Patent