Metacetamol

Metacetamol

Clinical data
Other names	N-Acetyl-meta-aminophenol; AMAP; meta-acetyl-aminophenol; 3-hydroxyacetanilide
Identifiers
IUPAC name N-(3-Hydroxyphenyl)acetamide
CAS Number	621-42-1  Y
PubChem CID	12124
ChemSpider	11626  Y
UNII	V942ZCN81H
ChEBI	CHEBI:76987  Y
ChEMBL	ChEMBL9419  Y
CompTox Dashboard (EPA)	DTXSID3022089
ECHA InfoCard	100.009.717
Chemical and physical data
Formula	C8H9NO2
Molar mass	151.165 g·mol−1
3D model (JSmol)	Interactive image
Melting point	146 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) Y Key:QLNWXBAGRTUKKI-UHFFFAOYSA-N Y

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. 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.