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Metacetamol

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Chemical compound Pharmaceutical compound
Metacetamol
Clinical data
Other namesN-Acetyl-meta-aminophenol; AMAP; meta-acetyl-aminophenol; 3-hydroxyacetanilide
Identifiers
IUPAC name
  • N-(3-Hydroxyphenyl)acetamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.009.717 Edit this at Wikidata
Chemical and physical data
FormulaC8H9NO2
Molar mass151.165 g·mol
3D model (JSmol)
Melting point146 to 149 °C (295 to 300 °F)
SMILES
  • CC(=O)NC1=CC(=CC=C1)O
InChI
  • InChI=InChI=InChI=1S/C8H9NO2/c1-6(10)9-7-3-2-4-8(11)5-7/h2-5,11H,1H3,(H,9,10)
  • Key:QLNWXBAGRTUKKI-UHFFFAOYSA-N

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.

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

References

  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 67–. ISBN 978-1-4757-2085-3.
  2. "CHEBI:76987 - metacetamol".
  3. ^ McGregor L, Rychkov DA, Coster PL, Day S, Drebushchak VA, Achkasov AF, et al. (2015). "A new polymorph of metacetamol" (PDF). CrystEngComm. 17 (32): 6183–6192. doi:10.1039/C5CE00910C. ISSN 1466-8033.
  4. Drebushchak VA, McGregor L, Rychkov DA (February 2017). "Cooling rate "window" in the crystallization of metacetamol form II". Journal of Thermal Analysis and Calorimetry. 127 (2): 1807–1814. doi:10.1007/s10973-016-5954-0. ISSN 1388-6150. S2CID 99391719.


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