Phenacetin

Phenacetin
Clinical data
ATC code	N02BE03 (WHO) ;
Identifiers
	IUPAC name N-(4-Ethoxyphenyl)acetamide;
CAS Number	62-44-2 ;
PubChem CID	4754;
IUPHAR/BPS	7402;
DrugBank	DB03783 ;
ChemSpider	4590 ;
UNII	ER0CTH01H9;
KEGG	D00569 ;
ChEBI	CHEBI:8050 ;
ChEMBL	ChEMBL16073 ;
CompTox Dashboard (EPA)	DTXSID1021116 ;
ECHA InfoCard	100.000.485
Chemical and physical data
Formula	C10H13NO2
Molar mass	179.219 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.24 g/cm3
Melting point	134 to 137.5 °C (273.2 to 279.5 °F)
Solubility in water	0.766 g/L (25 °C (77 °F))
	SMILES O=C(Nc1ccc(OCC)cc1)C;
	InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12) ; Key:CPJSUEIXXCENMM-UHFFFAOYSA-N ;
	(verify)

Phenacetin (/fɪˈnæsɪtɪn/ ^ⓘ; acetophenetidin, N-(4-ethoxyphenyl)acetamide) is a pain-relieving and fever-reducing drug, which was widely used following its introduction in 1887. It was withdrawn from medicinal use as dangerous from the 1970s (e.g., withdrawn in Canada in 1973, and by the U.S. Food and Drug Administration in 1983).

Clinical data


ATC code	N02BE03 (WHO)
Identifiers
IUPAC name N-(4-Ethoxyphenyl)acetamide
CAS Number	62-44-2^Y
PubChem CID	4754
IUPHAR/BPS	7402
DrugBank	DB03783^Y
ChemSpider	4590^Y
UNII	ER0CTH01H9
KEGG	D00569^Y
ChEBI	CHEBI:8050^Y
ChEMBL	ChEMBL16073^Y
CompTox Dashboard (EPA)	DTXSID1021116
ECHA InfoCard	100.000.485
Chemical and physical data
Formula	C₁₀H₁₃NO₂
Molar mass	179.219 g·mol⁻¹
3D model (JSmol)	Interactive image
Density	1.24 g/cm³
Melting point	134 to 137.5 °C (273.2 to 279.5 °F)
Solubility in water	0.766 g/L (25 °C (77 °F))
SMILES O=C(Nc1ccc(OCC)cc1)C
InChI InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)^Y Key:CPJSUEIXXCENMM-UHFFFAOYSA-N^Y
(verify)