Chemistry:Metacetamol

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Short description: Chemical compound
Metacetamol
Metacetamol-skeletal.svg
Clinical data
Other namesN-Acetyl-meta-aminophenol; AMAP; meta-acetyl-aminophenol; 3-hydroxyacetanilide
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC8H9NO2
Molar mass151.165 g·mol−1
3D model (JSmol)
Melting point146 to 149 °C (295 to 300 °F)

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

  1. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 67–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA67. 
  2. "CHEBI:76987 - metacetamol". http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:76987. 
  3. 3.0 3.1 3.2 "A new polymorph of metacetamol" (in en). CrystEngComm 17 (32): 6183–6192. 2015. doi:10.1039/C5CE00910C. ISSN 1466-8033. https://www.pure.ed.ac.uk/ws/files/23600768/C5CE00910C.pdf. 
  4. "Cooling rate "window" in the crystallization of metacetamol form II" (in en). Journal of Thermal Analysis and Calorimetry 127 (2): 1807–1814. February 2017. doi:10.1007/s10973-016-5954-0. ISSN 1388-6150.