Article · Wikipedia archive · Last revised Jul 25, 2026

Parapropamol

Parapropamol is a non-narcotic analgesic and impurity found in samples of the related and widely used analgesic paracetamol (acetaminophen).

Last revised
Jul 25, 2026
Read time
≈ 1 min
Length
330 w
Citations
9
Source
Wikipedia ↗
Parapropamol
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Names
IUPAC name
N-(4-Hydroxyphenyl)propanamide
Other names
  • Acetaminophen impurity B
  • para-hydroxypropionanilide
Identifiers
ChemSpider
ECHA InfoCard 100.015.359
UNII
Properties
C9H11NO2
Molar mass 165.192 g·mol−1
Appearance Pale purple solid
Melting point 170–172 °C (338–342 °F; 443–445 K)
Boiling point 389.9 °C (733.8 °F; 663.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Parapropamol is a non-narcotic analgesic and impurity found in samples of the related and widely used analgesic paracetamol (acetaminophen).123

Appearance

Parapropamol is a pale purple solid at room temperature.2

Structure

Parapropamol is a small molecule drug.4 Parapropamol is a structural analogue of paracetamol, containing an extra carbon in its chain. In the solid state, the compound assembles into multiple entangled 3-dimensional, hydrogen-bonded networks, like intertwined nets, called a 3D-interpenetrated supramolecular network. These networks have been reported for inorganic compounds such as SrAl2 and CeCu2,56 but parapropamol may be the first reported instance of an organic compound to exhibit this structure.17

References

References

  1. Li, Lin; Fei, Zhuan; Meng, Xiang-gao; Cao, Li-ping; Cai, Qun; Sun, Ren-qiang; Wu, An-xin (2013). "Organic hydrogen-bonded assembly of asymmetric phenol amide molecules". Structural Chemistry. 24 (5): 1419–1428. doi:10.1007/s11224-012-0168-y. ISSN 1040-0400.
  2. GHS, UN (2019). "N-(4-Hydroxyphenyl)propanamide Safety Data Sheets". Echemi. Retrieved 2026-01-11.
  3. "Acetaminophen Related Compound B (30 mg) (N-(4-hydroxyphenyl)propanamide)". store.usp.org. Retrieved 2026-01-11.
  4. "N-(4-Hydroxyphenyl)propanamide".
  5. O’Keeffe, Michael; Peskov, Maxim A.; Ramsden, Stuart J.; Yaghi, Omar M. (2008-12-16). "The Reticular Chemistry Structure Resource (RCSR) Database of, and Symbols for, Crystal Nets". Accounts of Chemical Research. 41 (12): 1782–1789. doi:10.1021/ar800124u. ISSN 0001-4842.
  6. Nuspl, Gerhard; Polborn, Kurt; Evers, Jürgen; Landrum, Gregory A.; Hoffmann, Roald (1996-11-20). "The Four-Connected Net in the CeCu(2) Structure and Its Ternary Derivatives. Its Electronic and Structural Properties". Inorganic Chemistry. 35 (24): 6922–6932. doi:10.1021/ic9602557. ISSN 1520-510X. PMID 11666868.
  7. Batten, Stuart R. (2010). Metal-Organic Frameworks: Design and Application. Hoboken, New Jersey: John Wiley & Sons, Inc. pp. 100–103. ISBN 978-0-470-19556-7.