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Metacetamol

Metacetamol
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
CompTox Dashboard (EPA)
ECHA InfoCard100.009.717 Edit this at Wikidata
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 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

  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. ^ a b c 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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