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Substance Name: Phenacetin [USP:INN:JAN]
RN: 62-44-2
UNII: ER0CTH01H9
InChIKey: CPJSUEIXXCENMM-UHFFFAOYSA-N

Note

  • A phenylacetamide that was formerly used in ANALGESICS but nephropathy and METHEMOGLOBINEMIA led to its withdrawal from the market. (From Smith and Reynard, Textbook of Pharmacology,1991, p431).

Molecular Formula

  • C10-H13-N-O2

Molecular Weight

  • 179.2177
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • TSCA Flag S (Substance is Identified in a Final Significant New Use Rule)
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 2A
  • Reasonably Anticipated to be a Carcinogen
  • Reportable Quantity (RQ) = 100 lb

Names and Synonyms

Name of Substance

  • Acetamide, N-(4-ethoxyphenyl)-
  • Acetophenetidin
  • N-(4-Ethoxyphenyl)acetamide
  • Phenacetin
  • Phenacetin [USP:INN:JAN]

MeSH Heading

  • Phenacetin

Synonyms

  • 1-Acetamido-4-ethoxybenzene
  • 4-13-00-01092 (Beilstein Handbook Reference)
  • 4-Ethoxyacetanilide
  • Acet-p-phenalide
  • Acetamide, N-(4-ethoxyphenyl)-
  • Acetanilide, 4'-ethoxy-
  • Acetic acid amide, N-(4-ethoxyphenyl)-
  • Aceto-4-phenetidine
  • Aceto-para-phenalide
  • Aceto-para-phenetidide
  • Acetophenetidin
  • Acetophenetidine
  • Acetophenetin
  • Acetphenetidin
  • Acetylphenetidin
  • Achrocidin
  • AI3-00783
  • Anapac
  • BRN 1869238
  • Bromo seltzer
  • Buff-A-Comp
  • CCRIS 496
  • Citra-fort
  • Clistanol
  • Codempiral
  • Commotional
  • Contradol
  • Contradouleur
  • Coricidin
  • Coriforte
  • Coryban-D
  • Daprisal
  • Dasikon
  • Dasin
  • Dasin CH
  • Dolostop
  • Edrisal
  • EINECS 200-533-0
  • Empiral
  • Emprazil
  • Emprazil-C
  • Epragen
  • Fenacetin
  • Fenacetin [Czech]
  • Fenacetina
  • Fenacetina [INN-Spanish]
  • Fenia
  • Fenidina
  • Fenina
  • Fortacyl
  • Gelonida
  • Gewodin
  • Helvagit
  • Hjorton's powder
  • Hocophen
  • HSDB 3152
  • KAFA
  • Kalmin
  • Malex
  • Melabon
  • Melaforte
  • N-(4-Ethoxyphenyl)acetamide
  • N-Acetyl-p-phenetidine
  • N-Acetyl-para-phenetidine
  • N-para-Ethoxyphenylacetamide
  • NSC 7651
  • p-Acetophenetide
  • p-Acetophenetidide
  • p-Acetophenetidine
  • p-Acetphenetidin
  • p-Ethoxyacetanilide
  • p-Ethoxyanilid kyseliny octove
  • p-Ethoxyanilid kyseliny octove [Czech]
  • p-Phenetidine, N-acetyl-
  • Pamprin
  • para-Acetophenetidide
  • para-Acetophenetidine
  • para-Acetphenetidin
  • para-Ethoxyacetanilide
  • para-Phenacetin
  • Paracetophenetidin
  • Paramette
  • Paratodol
  • Pertonal
  • Phenacet
  • Phenacetin
  • Phenacetine
  • Phenacetine [INN-French]
  • Phenacetinum
  • Phenacetinum [INN-Latin]
  • Phenacitin
  • Phenacon
  • Phenaphen
  • Phenaphen plus
  • Phenazetin
  • Phenazetina
  • Phenedina
  • Phenidin
  • Phenin
  • Phenodyne
  • Pyraphen
  • Pyrroxate
  • Quadronal
  • RCRA waste number U187
  • Robaxisal-PH
  • Salgydal
  • Sanalgine
  • Seranex
  • Sinedal
  • Sinubid
  • Sinutab
  • Sinutabs
  • Stellacyl
  • Super anahist
  • Synalogos
  • Tacol
  • Tetracydin
  • Thephorin A-C
  • Treupel
  • UNII-ER0CTH01H9
  • Veganine
  • Viden
  • Xaril

Systematic Names

  • Acetamide, N-(4-ethoxyphenol)-
  • Acetamide, N-(4-ethoxyphenyl)-
  • p-Acetophenetidide
  • Phenacetin

Superlist Names

  • Acetamide, N-(4-ethoxyphenyl)-
  • Phenacetin
  • Phenacetin [Analgesic mixtures containing phenacetin]
  • RCRA waste no. U187

Mixture Names

  • P-A-C Compound
  • Phensal

Registry Numbers

CAS Registry Number

  • 62-44-2

FDA UNII

  • ER0CTH01H9

System Generated Number

  • 0000062442

Structure Descriptors

InChI

InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)

InChIKey

CPJSUEIXXCENMM-UHFFFAOYSA-N

Smiles

CCOc1ccc(NC(=O)C)cc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 260mg/kg (260mg/kg)   National Technical Information Service. Vol. PB282-666,
guinea pig LD50 oral 1870mg/kg (1870mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Toxicology and Applied Pharmacology. Vol. 2, Pg. 23, 1960.
hamster LD50 oral 1690mg/kg (1690mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: ATAXIA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Pharmazie. Vol. 8, Pg. 572, 1953.
man LDLo unreported 74mg/kg (74mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 33900mg/m3 (33900mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 34(10), Pg. 36, 1969.
mouse LD50 intraperitoneal 540mg/kg (540mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 81, Pg. 659, 1961.
mouse LD50 oral 866mg/kg (866mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1644, 1978.
mouse LD50 subcutaneous 1625mg/kg (1625mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 25, 1958.
rabbit LD50 oral 2500mg/kg (2500mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 21(9), Pg. 53, 1977.
rabbit LD50 subcutaneous 1gm/kg (1000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 719, 1971.
rat LD50 intraperitoneal 634mg/kg (634mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 62, Pg. 11, 1966.
rat LD50 oral 1650mg/kg (1650mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 240, 1959.
rat LD50 oral 1650mg/kg (1650mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Toxicology and Applied Pharmacology. Vol. 1, Pg. 240, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 137.5 deg C   EXP
log P (octanol-water) 1.58 (none)   EXP
Water Solubility 766 mg/L 25 EXP
Vapor Pressure 6.92E-07 mm Hg 25 EXP
Henry's Law Constant 2.13E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.75E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.