Adafenoxate
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Names | |
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Preferred IUPAC name
2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate | |
Identifiers | |
3D model (JSmol)
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CompTox Dashboard (EPA)
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Properties | |
C20H26ClNO3 | |
Molar mass | 363.87834 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.[1]
Synthesis
Ex 1: 4-Chlorophenoxyacetic acid (pCPA) [122-88-3] is converted to its acid chloride to give 4-chlorophenoxyacetyl chloride [4122-68-3] (1). Esterification with 2-(1-adamantylamino)ethanol [3716-66-3] (2) gives Adafenoxate (3) in a single step.
Ex 2: Same as above but Fischer–Speier esterification done via a DS-trap. This gives an 88% yield.
References
- ^ Petkov VD, Getova D, Mosharrof AH (1987). "A study of nootropic drugs for anti-anxiety action". Acta Physiol Pharmacol Bulg. 13 (4): 25–30. PMID 2896427.
- ^ Romeo R. Andreoli, Xavier D. Cirera, U.S. patent 4,476,319 (1984 to Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A.).
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