(2E)-but-2-enedioic acid 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl acetate

• ChemBase ID: 159117
• Molecular Formular: C18H22N2O6
• Molecular Mass: 362.37708
• Monoisotopic Mass: 362.14778643
• SMILES: c1cc(c2c(c1)[nH]cc2CCN(C)C)OC(=O)C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: CN(CCc1c[nH]c2c1c(ccc2)OC(=O)C)C.OC(=O)/C=C/C(=O)O
• InChI: InChI=1S/C14H18N2O2.C4H4O4/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3;5-3(6)1-2-4(7)8/h4-6,9,15H,7-8H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+
• InChIKey: QIJLOAPCCJQEEZ-WLHGVMLRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-but-2-enedioic acid 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl acetate
• IUPAC Traditional name: O-acetylpsilocin; fumaric acid
• Synonyms: 3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Acetate Fumarate; O-Acetyl Psilocin Fumarate

Database IDs

• PubChem SID: 162253252
• PubChem CID: 71312811

CALCULATED PROPERTIES

• Acid pKa: 17.055525
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.477355
• LogD (pH = 7.4): -0.19701119
• Log P: 1.9093268
• Molar Refractivity: 71.5746 cm^3
• Polarizability: 28.791378 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A187520

It is readily crystallized as the fumarate salt, and is considerably more stable than Psilocin (P839630) itself. It would seem to be an ideal prodrug to replace Psilocybin in future clinical studies, since Psilocin is the principal metabolite of Psilocibi

REFERENCES

• Migliaccio, G., et al.: J. Med. Chem., 24, 206 (1981)
• Strassman, R., et al.: Arch. Gen. Psych., 51, 85 (1981)
• Hasler, F., et al.: Pharm. Acta Helv., 72, 175 (1981)