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62-44-2 molecular structure
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N-(4-ethoxyphenyl)acetamide

ChemBase ID: 3432
Molecular Formular: C10H13NO2
Molecular Mass: 179.21572
Monoisotopic Mass: 179.09462866
SMILES and InChIs

SMILES:
O(c1ccc(NC(=O)C)cc1)CC
Canonical SMILES:
CCOc1ccc(cc1)NC(=O)C
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

Cite this record

CBID:3432 http://www.chembase.cn/molecule-3432.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-(4-ethoxyphenyl)acetamide
IUPAC Traditional name
phenacetin
Brand Name
Contradouleur
Achrocidin
Codempiral
Commotional
Contradol
Synonyms
Acetophenetidin
Acetophenetidine
Acetophenetin
Acetphenetidin
Phenacetin
4-Acetophenetidide
Phenacetin
4'-Ethoxyacetanilide
4-(Acetylamino)phenetole
4-Ethoxy-1-acetylaminobenzene
4-Ethoxyacetanilide
4'-Ethoxyacetanilide
Aceto-4-phenetidine
Fenidina
Fenina
Kalmin
N-Acetyl-4-ethoxyaniline
N-Acetyl-p-ethoxyaniline
N-Acetyl-p-phenetidine
NSC 7651
Pertonal
Phenacetine
Phenazetin
Phenedina
Phenidin
Phenin
p-Ethoxyacetanilide
1-Acetyl-p-phenetidin
4′-Ethoxyacetanilide
N-(4-Ethoxyphenyl)acetamide
p-Acetophenetidide
Phenacetin
N-(4-ethoxyphenyl)acetamide
4'-乙氧基乙酰苯胺
N-(4-乙氧苯基)乙酰胺
乙酰乙氧基苯胺
乙酰对氨基苯乙醚
对乙氧基乙酰苯胺
对乙酰乙氧基苯胺
非那西丁
CAS Number
62-44-2
EC Number
200-533-0
MDL Number
MFCD00009094
Beilstein Number
1869238
Merck Index
147204
PubChem SID
160966871
24890660
46507394
24854118
24887192
PubChem CID
4754

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.978987  H Acceptors
H Donor LogD (pH = 5.5) 1.4100928 
LogD (pH = 7.4) 1.4100928  Log P 1.4100928 
Molar Refractivity 52.1328 cm3 Polarizability 19.564053 Å3
Polar Surface Area 38.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.62  LOG S -2.0 
Solubility (Water) 1.78e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
133-136 °C(lit.) expand Show data source
134-136°C expand Show data source
135-137°C expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Storage Warning
Hygroscopic expand Show data source
RTECS
AM4375000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
45-22 expand Show data source
Safety Statements
53-20-36-45 expand Show data source
53-45 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H350 expand Show data source
H350-H302 expand Show data source
GHS Precautionary statements
P201-P308 + P313 expand Show data source
P281-P264-P301+P312-P308+P313-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Pharmacopeia Traceability
traceable to USP 1514008 expand Show data source
Linear Formula
CH3CONHC6H4OC2H5 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB03783 external link
Item Information
Drug Groups experimental; withdrawn
Description Phenacetin was withdrawn from the Canadian market in June 1973 due to concerns regarding nephropathy (damage to or disease of the kidney).
Indication Used principally as an analgesic.
Pharmacology Phenacetin was the first NSAID and fever reducer to go on the market. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action of the heart, where it acts as a negative inotrope. It is an antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat rheumatoid arthritis (subacute type), intercostal neuralgia, and some forms of ataxia. [Wikipedia]
Affected Organisms
Humans and other mammals
References
Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. [Pubmed]
Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. [Pubmed]
TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. [Pubmed]
Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. [Pubmed]
External Links
Wikipedia
DrugBank - DB08243 external link
Drug information: experimental
Selleck Chemicals - S2577 external link
Research Area: Inflammation
Biological Activity:
Phenacetin is a non-opioid analgesic without anti-inflammatory properties. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action on the heart, where it acts as a negative inotrope. Phenacetin is an antipyretic, acting on the brain to decrease the temperature set point. Phenacetin is also used to treat rheumatoid arthritis (subacute type) and intercostal neuralgia. [1][2]References on Phenacetin[1] http://en.wikipedia.org/wiki/Phenacetin, , [2] N Engl J Med. , 1991 Jan 17, 324(3):155-60
Sigma Aldrich - A2500 external link
Biochem/physiol Actions
CYP1A2 和 CYP2D6 的底物。
Sigma Aldrich - 235830 external link
Biochem/physiol Actions
Substrate of CYP1A2 and CYP2D6.
Packaging
5, 500 g in glass bottle
Sigma Aldrich - 77440 external link
Biochem/physiol Actions
Substrate of CYP1A2 and CYP2D6.
Packaging
1 kg in poly bottle
50, 250 g in poly bottle
Sigma Aldrich - 44207 external link
Biochem/physiol Actions
Substrate of CYP1A2 and CYP2D6.
Toronto Research Chemicals - P294580 external link
Analgesic, antipyretic. Component of APC tablets, analgesic mixture also containing aspirin and caffeine. Phenacetin is reasonably anticipated to be a human carcinogen; analgesic mixtures containing Phenacetin are listed as known human carcinogens.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Dubach UC, Rosner B, Sturmer T: An epidemiologic study of abuse of analgesic drugs. Effects of phenacetin and salicylate on mortality and cardiovascular morbidity (1968 to 1987) N Engl J Med. 1991 Jan 17;324(3):155-60. Pubmed
  • • Brix AE: Renal papillary necrosis. Toxicol Pathol. 2002 Nov-Dec;30(6):672-4. Pubmed
  • • Cochran AJ, Lawson DH, Linton AL: Renal papillary necrosis following phenacetin excess. Scott Med J. 1967 Jul;12(7):246-50. Pubmed
  • • TAN GH, RABBINO MD, HOPPER J Jr: IS PHENACETIN A NEPHROTOXIN?A REPORT ON TWENTY-THREE USERS OF THE DRUG. Calif Med. 1964 Aug;101:73-7. Pubmed
  • • Boyd, et al.: Toxicol. Appl. Pharmacol., 1, 240 (1959)
  • • Dubach, C.U., et al.: N. Engl. J. Med., 308, 357 (1959)
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PATENTS

PATENTS

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