Basic information
- Standard SMILES
CC(=O)Nc1ccc(O)cc1- InChIKey
RZVAJINKPMORJF-UHFFFAOYSA-N- Molecular formula
- C8H9NO2
- Average molar mass
- 151.16 g/mol
- Monoisotopic mass
- 151.06332853
Names & identifiers
- Preferred name
- Acetaminophen
- IUPAC
- N-(4-hydroxyphenyl)acetamide
- English name
- Acetaminophen
- Molecular formula
- C8H9NO2
- Molecular weight
- 151.16
Names & synonyms
Show more names
Database identifiers
- CAS
103-90-2- PubChem CID
- 1983
- DTXSID
DTXSID2020006- ChEMBL
CHEMBL112- ChEBI
CHEBI:46195- UNII
- 362O9ITL9D
- EC Number
- 203-157-5
- Nikkaji
- J4.025H
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 139
Physicochemical properties
- Melting point
- 168 · 168-172 °C(lit.)
- Boiling point
- 273.17 °C · 273.17°C (rough estimate)
- Density
- 1 · 1,293 g/cm3
- vapor pressure
- 0.008 Pa · 0.008Pa at 25℃
- refractive index
- 1.581 · 1.5810 (rough estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 0.5 M, · ethanol: soluble0.5M, clear, colorless
- form
- Crystals or Crystalline Powder
- pka
- 9.86 · 9.86±0.13(Predicted)
- color
- White
- PH
- 5.5 · 5.5-6.5 (H2O, 20℃)(saturated solution)
- Odor
- odorless
- PH Range
- 5.5 · 5.5 - 6.5 (HO, 20 °C) (saturated solution)
- explosive limit
- 15 % · 15%(V)
- Water Solubility
- 14 g/L · 14 g/L (20 ºC)
- Merck
- 14 · 14,47
- BRN
- 2208089 · 2208089
- Henry's Law Constant
- 1.5 · 1.5×107 mol/(m3Pa) at 25℃, HSDB (2015)
- BCS Class
- 3 · 3,4
- Major Application
- pharmaceutical (small molecule)
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
- InChI
- 1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
- InChIKey
- RZVAJINKPMORJF-UHFFFAOYSA-N
- SMILES
- CC(=O)Nc1ccc(O)cc1
- LogP
- 1.098 at · 1.098 at 25℃
- Toxicology and Carcinogenesis
- Toxicology and Carcinogenesis Studies of Acetaminophen (CASRN 103-90-2) in F344/N Rats and B6C3F1 Mice (Feed Studies)
- CAS DataBase Reference
- 103 · 103-90-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- acetaminophen
- FDA UNII
- 362 O9ITL9D · 362O9ITL9D
- NCI Drug Dictionary
- acetaminophen
- ATC code
- 2 BE01 · N02BE01
- NIST Chemistry Reference
- Acetaminophen(103-90-2)
- IARC
- 3 · 3 (Vol. 50, 73) 1999
- EPA Substance Registry System
- Acetaminophen (103-90-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Protein binding
- 20 · 20-30%
- Excreted unchanged in urine
- 5 % · <5%
- Volume of distribution
- 1 · 1-2(L/kg)
- Biological half-life
- 1 · 1-4 / Unchanged
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,T,F
- Risk Statements
- 22 · 22-36/37/38-52/53-36/38-40-39/23/24/25-23/24/25-11
- Safety Statements
- 26 · 26-36-61-37/39-22-45-36/37-16-7
- RIDADR
- 3077 · UN 3077 9/PG III
- WGK Germany
- 1 · 1
- RTECS
- 4200000 · AE4200000
- Autoignition Temperature
- 540 °C · 540 °C
- TSCA
- TSCA listed
- HazardClass
- 9 · 9
- PackingGroup
- III
- HS Code
- 29242930 · 29242930
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Hazardous Substances Data
- 103 · 103-90-2(Hazardous Substances Data)
- Toxicity
- 50 in · LD50 in mice (mg/kg): 338 orally (Starmer), 500 i.p. (Dahlin, Nelson)
- REACH Registrations
- Active
Safety & regulation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- AE4200000
- ridadr
- UN 3077 9/PG III
- hs_code
- 29242930
- Toxicity
- LD50 in mice (mg/kg): 338 orally (Starmer), 500 i.p. (Dahlin, Nelson)
- risk_code
- 22-36/37/38-52/53-36/38-40-39/23/24/25-23/24/25-11
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T,F
- safety_code
- 26-36-61-37/39-22-45-36/37-16-7
- hazard_class
- 9
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Autoignition Temperature
- 540 °C
- Precautionary statements
- P264-P270-P301+P312-P501
- Hazardous Substances Data
- 103-90-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionAcetaminophen differs from the nonsteroidal anti-inflammatory agents described in that it is devoid of anti-inflammatory and antirheumatic properties. It was recently shown that acetaminophen, like aspirin, inhibits cyclooxygenase action in the brain and is even stronger than aspirin. On the other hand, the mechanism of analgesic action of acetaminophen is not fully clear, since it acts poorly on peripheral cyclooxygenase.
DescriptionAcetaminophen is an analgesic and antipyretic compound. Unlike many NSAIDs, which inhibit both COX-1 and COX-2, early studies suggested that acetaminophen is a poor inhibitor of both isoforms. However, it does inhibit COX-2 by 83% and COX-1 by 56% in human blood ex vivo, albeit at a high 1,000 mg dose, with IC50 values of 25.8 and 113.7 μM, respectively. Acetaminophen is enzymatically and non-enzymatically converted to several reactive metabolites that contribute to adverse or indirect effects, including liver injury. At toxic doses, the acetaminophen metabolite N-acetyl-4-benzoquinone imine (NAPQI; ) depletes glutathione reserves in the liver, leading to an accumulation of NAPQI and subsequent hepatocyte necrosis. Acetaminophen decreases glutathione levels and reduces glutathione peroxidase activity in mice when administered at a dose of 250 mg/kg and induces ferroptotic cell death in primary mouse hepatocytes, an effect that can be blocked by the ferroptosis inhibitor ferrostatin-1 . Acetaminophen has analgesic and antipyretic properties in animal models.
HistoryAcetaminophen was first discovered by H. N. Morse in 1878. Although many studies on its use as an analgesic were performed, it wasn’t until 1950 that it was marketed under the name Triagesic. Today, its most common trade names are Tylenol and Panadol, but a large percentage of its sales are as a generic drug. It is the most commonly used medication for pain and fever in both the United States and Europe. It is on the World Health Organization's List of Essential Medicines.
UsesAnalgesic; antipyretic
Usesantiinfectant
Usesdispersing agent in liquid scintillation counting
Usesmanufacture of azo dyes, photographic chemicals.
UsesAcetaminophen is widely used as an analgesic and fever-reducing agent. Acetaminophen is designed for moderate analgesia. It is also effective like aspirin and is used in analgesia for headaches (from weak to moderate pain), myalgia, arthralgia, chronic pain, for oncological and post-operational pain, etc.
General DescriptionOdorless white crystalline solid. Bitter taste. pH (saturated aqueous solution) about 6.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: Paracetamol is a member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group. It has a role as a cyclooxygenase 2 inhibitor, a cyclooxygenase 1 inhibitor, a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic, an environmental contaminant, a human blood serum metabolite, a hepatotoxic agent, a ferroptosis inducer and a geroprotector. It is a member of phenols and a member of acetamides. It is functionally related to a 4-aminophenol.
Related reactions
Linked notes
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