Metacetamol

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Structural formula
Metacetamol structural formula
General
Non-proprietary name Metacetamol
other names
  • N -acetyl-3-aminophenol
  • N -acetyl- m -aminophenol
  • 3-acetaminophenol
  • AMAP
  • 3'-hydroxyacetanilide
  • m -hydroxyacetanilide
  • N - (3-hydroxyphenyl) acetamide ( IUPAC )
  • med. Abbr . : MCM
Molecular formula C 8 H 9 NO 2
Brief description

beige solid

External identifiers / databases
CAS number 621-42-1
EC number 210-687-0
ECHA InfoCard 100.009.717
PubChem 12124
Wikidata Q27146503
Drug information
Drug class
properties
Molar mass 151.16 g · mol -1
Melting point

145-148 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319
P: 305 + 351 + 338
Toxicological data

1025 mg kg −1 ( LD 50 ,  mouse ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Metacetamol is a non-toxic regioisomer of paracetamol with analgesic and antipyretic properties, but never as a drug has been marketed.

A 1980 scientific study suggested that metacetamol might be a safer analgesic and antipyretic than paracetamol .

The compound has a monoclinic crystal structure with space group P 2 1 (space group no. 4) . Two other orthorhombic crystal structures are known. Template: room group / 4

Extraction and presentation

Metacetamol can be obtained by reacting m -aminophenol with acetic acid.

Individual evidence

  1. ↑ a b c d e Data sheet 3-Acetamidophenol, 97% from Sigma-Aldrich , accessed on January 4, 2019 ( PDF ).
  2. ↑ CHEBI: 76987 - metacetamol. Retrieved December 29, 2018 .
  3. ^ Edward B Nelson: The pharmacology and toxicology of meta-substituted acetanilide I: acute toxicity of 3-hydroxyacetanilide in mice In: Research communications in chemical pathology and pharmacology 1980
  4. ↑ Lindsay McGregor, Denis A. Rychkov u. a .: A new polymorph of metacetamol. In: CrystEngComm. 17, 2015, p. 6183, doi : 10.1039 / c5ce00910c .
  5. ↑ VA Drebushchak, L. McGregor, DA Rychkov: . Cooling rate "window" in the crystallization of form II metacetamol In: Journal of Thermal Analysis and Calorimetry. 127, 2017, p. 1807, doi : 10.1007 / s10973-016-5954-0 .
  6. ↑ Sumana T., Pushpa Iyengar, Sanjeevarayappa C., Manoj Kumar KE, Vijay K .: Synthesis, Characterization and Pharmacological study of Metacetamol derivatives