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 ;
PubChem CID	12124;
ChemSpider	11626 ;
UNII	V942ZCN81H;
ChEBI	CHEBI:76987 ;
ChEMBL	ChEMBL9419 ;
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) ; 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.[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

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.
"CHEBI:76987 - metacetamol".
McGregor, Lindsay; Rychkov, Denis A.; Coster, Paul L.; Day, Sarah; Drebushchak, Valeri A.; Achkasov, Andrei F.; Nichol, Gary S.; Pulham, Colin R.; Boldyreva, Elena V. (2015). "A new polymorph of metacetamol". CrystEngComm. 17 (32): 6183–6192. doi:10.1039/C5CE00910C. ISSN 1466-8033.
Drebushchak, V. A.; McGregor, L.; Rychkov, D. A. (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.

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[Elks2014-1] 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".

[:0-3] McGregor, Lindsay; Rychkov, Denis A.; Coster, Paul L.; Day, Sarah; Drebushchak, Valeri A.; Achkasov, Andrei F.; Nichol, Gary S.; Pulham, Colin R.; Boldyreva, Elena V. (2015). "A new polymorph of metacetamol". CrystEngComm. 17 (32): 6183–6192. doi:10.1039/C5CE00910C. ISSN 1466-8033.

[4] Drebushchak, V. A.; McGregor, L.; Rychkov, D. A. (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.