(2E)-but-2-enedioic acid 3-[2-(dimethylamino)(2H4)ethyl]-1H-indol-4-yl acetate

• ChemBase编号: 159118
• 分子式: C18H22N2O6
• 平均质量: 362.37708
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2E)-but-2-enedioic acid 3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-4-yl acetate
• IUPAC传统名: fumaric acid 3-[2-(dimethylamino)(^2H₄)ethyl]-1H-indol-4-yl acetate
• 别名: 3-[2-(Dimethylamino)ethyl-d4]-1H-indol-4-ol 4-Acetate Fumarate; O-Acetyl Psilocin-d4 Fumarate

登记号

• PubChem SID: 162253253
• PubChem CID: 71312812

理论计算性质

• Acid pKa: 17.055525
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): -1.477355
• LogD (pH = 7.4): -0.19701119
• Log P: 1.9093268
• 摩尔折射率: 71.5746 cm^3
• 极化性: 28.87168 Å^3
• 极化表面积: 45.33 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: true

详细说明

Toronto Research Chemicals - A187522

Labelled O-Acetyl Psilocin (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

参考文献

• 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)