Metacetamol

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Metacetamol
File:Metacetamol-skeletal.svg
Clinical data
Other namesN-Acetyl-meta-aminophenol; AMAP; meta-acetyl-aminophenol; 3-hydroxyacetanilide
Identifiers
  • N-(3-Hydroxyphenyl)acetamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC8H9NO2
Molar mass151.165 g·mol−1
3D model (JSmol)
Melting point146 to 149 °C (295 to 300 °F)
  • CC(=O)NC1=CC(=CC=C1)O
  • InChI=InChI=InChI=1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10) checkY
  • Key:QLNWXBAGRTUKKI-UHFFFAOYSA-N checkY

Metacetamol (developmental code name BS-749), also known as 3-hydroxyacetanilide and AMAP, is a non-toxic regioisomer of paracetamol with analgesic and antipyretic properties, but has never been marketed as a drug.[1][2]

Metacetamol is known to have several polymorphs.[3] Form II is metastable, while form I is stable.[3] Metacetamol polymorph II transforms to form I upon water moisture or direct contact with water and other popular solvents.[3] Metacetamol II form may be obtained on cooling in narrow temperature regime.[4]

References

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