Adafenoxate

Adafenoxate
Names
	Preferred IUPAC name 2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate
Identifiers
CAS Number	82168-26-1 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2104053 ;
ChemSpider	58080 ;
PubChem CID	64517;
UNII	B8VQU4C05J ;
CompTox Dashboard (EPA)	DTXSID4046280 ;
	InChI InChI=1S/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2 Key: PLSMXIQMWYSHIV-UHFFFAOYSA-N ; InChI=1/C20H26ClNO3/c21-17-1-3-18(4-2-17)25-13-19(23)24-6-5-22-20-10-14-7-15(11-20)9-16(8-14)12-20/h1-4,14-16,22H,5-13H2 Key: PLSMXIQMWYSHIV-UHFFFAOYAK;
	SMILES Clc4ccc(cc4)OCC(=O)OCCNC12CC3CC(C1)CC(C2)C3;
Properties
Chemical formula	C20H26ClNO3
Molar mass	363.88 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.^[1]

Synthesis

Adafenoxate can be prepared starting with 4-chlorophenoxyacetic acid (pCPA) by converting it to its acid chloride to give 4-chlorophenoxyacetyl chloride (1).^[2] Esterification with 2-(1-adamantylamino)ethanol (2) gives adafenoxate (3).

Alternatives, the final step can be accomplished via Fischer–Speier esterification using a Dean-Stark trap.

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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[pmid2896427-1] 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.

[2] Romeo R. Andreoli, Xavier D. Cirera, U.S. patent 4,476,319 (1984 to Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A.).

[1]