Adafenoxate

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| verifiedrevid = 477241824

| ImageFile = Adafenoxate.svg

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| ImageSize = 200

| PIN = 2-[(Adamantan-1-yl)amino]ethyl (4-chlorophenoxy)acetate

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| Section1 = {{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = B8VQU4C05J

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 58080

| 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

| InChIKey = PLSMXIQMWYSHIV-UHFFFAOYAK

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PLSMXIQMWYSHIV-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo=82168-26-1

| PubChem=64517

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104053

| SMILES = Clc4ccc(cc4)OCC(=O)OCCNC12CC3CC(C1)CC(C2)C3

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| Section2 = {{Chembox Properties

| C=20 | H=26 | Cl=1 | N=1 | O=3

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Adafenoxate is a compound related to centrophenoxine, that has been found to act as a nootropic in rats.{{cite journal |vauthors =Petkov VD, Getova D, Mosharrof AH |title=A study of nootropic drugs for anti-anxiety action |journal=Acta Physiol Pharmacol Bulg |volume=13 |issue=4 |pages=25–30 |year=1987 |pmid=2896427 }}

Synthesis

Adafenoxate can be prepared starting with 4-chlorophenoxyacetic acid (pCPA) by converting it to its acid chloride to give 4-chlorophenoxyacetyl chloride (1).Romeo R. Andreoli, Xavier D. Cirera, {{US patent|4476319}} (1984 to Sociedad Espanola De Especialidades Farmaco-Terapeuticas S.A.). Esterification with 2-(1-adamantylamino)ethanol (2) gives adafenoxate (3).

File:Adafenoxate synthesis.svg

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

References

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{{Acetylcholine receptor modulators}}

Category:Adamantanes

Category:4-Chlorophenyl compounds

Category:Cholinergics

Category:Amines

Category:Nootropics

Category:Phenoxyacetic acids

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