({3-[2-(dimethylamino)(2H4)ethyl]-1H-indol-4-yl}oxy)phosphonic acid

• ChemBase ID: 177104
• Molecular Formular: C12H17N2O4P
• Molecular Mass: 284.248141
• Monoisotopic Mass: 284.09259366
• SMILES: c1cc(c2c(c1)[nH]cc2CCN(C)C)OP(=O)(O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ({3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-4-yl}oxy)phosphonic acid
• IUPAC Traditional name: {3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-4-yl}oxyphosphonic acid
• Synonyms: 3-[2-(Dimethylamino)ethyl-d4]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester; 4-Phosphoryl-N,N-dimethyltryptamine-d4; Cy 39-d4; Indocybin-d4; Psilocybine-d4; O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine-d4; Psilocine-d4 Phosphate; Psilocybin-d4

Database IDs

• PubChem SID: 164233014
• PubChem CID: 71751874

CALCULATED PROPERTIES

• Acid pKa: 1.7443777
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.15883611
• LogD (pH = 7.4): -0.89353734
• Log P: -0.13636683
• Molar Refractivity: 73.296 cm^3
• Polarizability: 29.268513 Å^3
• Polar Surface Area: 85.79 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 215-217°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - P839652

Labelled Psilocybin. The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being Psilocin. Psychomimetic.Controlled substance (hallucinogen).

REFERENCES

• 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)