Home > Compound List > Compound details
520-52-5 molecular structure
click picture or here to close

({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

ChemBase ID: 129168
Molecular Formular: C12H17N2O4P
Molecular Mass: 284.248141
Monoisotopic Mass: 284.09259366
SMILES and InChIs

SMILES:
CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12
Canonical SMILES:
CN(CCc1c[nH]c2c1c(ccc2)OP(=O)(O)O)C
InChI:
InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)
InChIKey:
QVDSEJDULKLHCG-UHFFFAOYSA-N

Cite this record

CBID:129168 http://www.chembase.cn/molecule-129168.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
({3-[2-(dimethylamino)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
IUPAC Traditional name
psilocybin
Synonyms
Psilocybin
3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester
4-Phosphoryl-N,N-dimethyltryptamine
Cy 39
Indocybin
Psilocybine
O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine
Psilocine Phosphate
3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl phosphate
Psilocybin
CAS Number
520-52-5
EC Number
208-294-4
MDL Number
MFCD01310431
Beilstein Number
273158
PubChem SID
162223465
PubChem CID
10624
CHEBI ID
8614
CHEMBL
194378
Chemspider ID
10178
KEGG ID
C07576
MeSH Name
Psilocybine
Wikipedia Title
Psilocybin

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.7443777  H Acceptors
H Donor LogD (pH = 5.5) -0.15883611 
LogD (pH = 7.4) -0.89353734  Log P -0.13636683 
Molar Refractivity 73.296 cm3 Polarizability 29.192675 Å3
Polar Surface Area 85.79 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
H2O: >20 mg/mL expand Show data source
Methanol (Hot), expand Show data source
soluble in methanol
slightly soluble in ethanol
negligible in chloroform, benzene
expand Show data source
soluble in water expand Show data source
Water expand Show data source
Apperance
solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
226-2280C expand Show data source
Storage Condition
Controlled Substance, -20°C Freezer expand Show data source
RTECS
NM3150000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
LD50
285 mg/kg (mouse, i.v.)
280 mg/kg (rat, i.v.)
12.5 mg/kg (rabbit, i.v.)
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Drug Control
USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada expand Show data source
Storage Temperature
-20°C expand Show data source
Admin Routes
Oral, intravenous expand Show data source
Dependency Liability
Low expand Show data source
Excretion
Renal expand Show data source
Half Life
oral: 163±64 min
intravenous: 74.1±19.6 min
expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Class A (UK) expand Show data source
S9 (Australia) expand Show data source
Schedule I (US) expand Show data source
Schedule III (Canada) expand Show data source
Purity
≥98% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C12H17N2O4P expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - P0100 external link
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 external link
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 IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle 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)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle