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4-Acetamidophenol(CAS No. 103-90-2)

4-Acetamidophenol C8H9NO2 (cas 103-90-2) Molecular Structure

103-90-2 Structure

Identification and Related Records

【Name】
4-Acetamidophenol
【CAS Registry number】
103-90-2
【Synonyms】
Acetaminophen
4-Hydroxyacetanilide
Paracetamol
APAP
p-Hydroxyacetanilide
Paracetamol (Acetaminophen)
4-Acetamino phenol
Acetaminphen
【EINECS(EC#)】
203-157-5
【Molecular Formula】
C8H9NO2 (Products with the same molecular formula)
【Molecular Weight】
151.16
【Inchi】
InChI=1/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
【InChIKey】
RZVAJINKPMORJF-UHFFFAOYSA-N
【Canonical SMILES】
CC(=O)NC1=CC=C(C=C1)O
【MOL File】
103-90-2.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.293
【Melting Point】
168-172℃
【Boiling Point】
387.8 °C at 760 mmHg
【Refractive Index】
1.619
【Flash Point】
387.8 °C at 760 mmHg
【Water】
14 g/L (20℃)
【Solubilities】
miscible
【Color/Form】
Large monoclinic prisms from water
【Stability】
Stable under normal temperatures and pressures.
【HS Code】
29242930
【Storage temp】
Store in a cool, dry place. Keep container closed when not in use.
【Spectral properties】
UV max (ethanol): 250 nm (epsilon 13800)
Intense mass spectral peaks: 80 m/z, 109 m/z, 151 m/z
MASS: 4765 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
IR: 5420 (Coblentz Society spectral collection)
UV: 2913 (Sadtler Research Laboratories spectral collection)
Raman: 930 (Sadtler Research Laboratories spectral collection)
【Computed Properties】
Molecular Weight:151.16256 [g/mol]
Molecular Formula:C8H9NO2
XLogP3:0.5
H-Bond Donor:2
H-Bond Acceptor:2
Rotatable Bond Count:1
Tautomer Count:6
Exact Mass:151.063329
MonoIsotopic Mass:151.063329
Topological Polar Surface Area:49.3
Heavy Atom Count:11
Formal Charge:0
Complexity:139
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:2
Conformer Sampling RMSD:0.4
CID Conformer Count:2

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22;R36/38;R52/53
【Safety Statements 】
S26;S37/39;S61
【Safety】

Hazard Codes of Paracetamol (CAS NO.103-90-2):?HarmfulXn
Risk Statements: 22-36/37/38-52/53-40?
R22: 3Harmful if swallowed.?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R40: Limited evidence of a carcinogenic effect.
Safety Statements: 26-36-61-37/39-22?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36: Wear suitable protective clothing.?
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.?
S37/39: Wear suitable gloves and eye/face protection.?
S22: Do not breathe dust.
WGK Germany: 1
RTECS: AE4200000
HS Code:?29242930

【Transport】
25kgs
【Formulations/Preparations】
DRUG AVAILABLE GENERICALLY: CAPSULES 500 MG; DROPS 100 MG/ML; ELIXIR 80, 120, 130, 160 AND 325 MG/5 ML; TABLETS 80 (CHEWABLE) 325, 500, AND 650 MG; SUPPOSITORIES 120, 325, AND 650 MG (ALL FORMS NONPRESCRIPTION).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl acetaminophen, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

Paracetamol is extremely toxic to cats,paracetamol is also lethal to snakes。

【Octanol/Water Partition Coefficient】
log Kow = 0.46

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... From p-nitrophenol by reduction with tin in glacial acetic acid ... From p-aminophenol by action of glacial acetic acid & acetic anhydride ... By action of ketene on p-aminophenol ... From p-hydroxyacetophenone hydrazone ... .
Production is by the acetylation of 4-aminophenol.
Preparation: ... Wilbert, De Angelis, US 2998450 (1961 to Warner Lambert).
U.S. Imports

(1972) 9.1X10+7 GRAMS (PRINCPL CUSTMS DISTS)
(1975) 3.46X10+8 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production

(1975) 4.5X10+9 GRAMS (INCL PHENACETIN)
(1976) GREATER THAN 2.27X10+6 GRAMS
Acetaminophen was one of the most used pharmaceuticals in England during 2002, at an amount used per year of 390,954.26 kg and has been detected in the environment.
Consumption Patterns

PRINCIPALLY USED AS A MEDICINAL (1976).
Acetaminophen. Analgesic, 75%; exports, 25%.
CHEMICAL PROFILE: Acetaminophen. Demand: 1987: 30 million lb; 1988: 30.5 million lb; 1992 /projected/: 31.5 million lb (Includes exports, but not imports, which totaled about 5 million lb last year.)
【Usage】

Analgesic; antipyretic

Biomedical Effects and Toxicity

【Biological Activity】
Cyclooxygenase inhibitor; may be selective for COX-3 (IC 50 values are 460, > 1000 and > 1000 μ M for canine COX-3, and murine COX-1 and COX-2 respectively). Widely used analgesic and antipyretic agent.
【Pharmacological Action】
- A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.
- Drugs that are used to reduce body temperature in fever.
【Therapeutic Uses】
Analgesics, Non-Narcotic
Acetaminophen is indicated to relieve mild to moderate pain and reduce fever. It provides symptomatic relief only; additional therapy to treat the cause of the pain or fever should be instituted when necessary. /Included in US product label/
Acetaminophen has minimal anti-inflammatory activity and does not relieve redness, swelling, or stiffness due to arthritis; it can not be use in place of aspirin or other salicylates or other nonsteroidal anti-inflamatory drugs (NSAIDs) in the treatment of rheumatoid arthritiss. However, it may be used to relieve pain due to mild osteoarthritis. /included in US product label/
Acetaminophen may be used when aspirin therapy is contradicted or inadvisable, e.g., in patients receiving anticoagulants or uricosuric agents, patients with hemophilia or other bleeding problems, and those with upper gastrointestinal disease or intolerance or hypersensitivity to aspirin. /Included in US product label/
Acute tension-type headaches with mild to moderate pain may be treated with a nonopiate analgesic such as ... acetaminophen ... .
/Acetaminophen/ is used to treat headache, mild to moderate myalgia, arthralgia, chronic pain of cancer, postpartum pain, postoperative pain, and fever.
MEDICATION (VET): In arthritic & inflammatory syndromes to relieve pain & reduce fever.
【Biomedical Effects and Toxicity】
Acetaminophen is rapidly and almost completely absorbed from the GI tract following oral administration. In healthy men, steady-state oral bioavailability of 1.3-g doses of extended-release tablets of acetaminophen administered every 8 hours for a total of 7 doses was equal to 1-g doses of conventional tablets of acetaminophen given every 6 hours for a total of 7 doses. Food may delay slightly absorption of extended-release tablets of acetaminophen. Following oral administration of immediate- or extended-release acetaminophen preparations, peak plasma concentrations are attained within 10-60 or 60-120 minutes, respectively. Following oral administration of a single 500-mg conventional tablet or a single 650-mg extended-release tablet, average plasma acetaminophen concentrations of 2.1 or 1.8 ug/mL, respectively, occur at 6 or 8 hours, respectively. In addition, dissolution of the extended-release tablets may depend slightly on the gastric or intestinal pH. Dissolution appears to be slightly faster in the alkaline pH of the intestines compared with the acidic pH of the stomach; however, this is of no clinical importance. Following administration of conventional preparations of acetaminophen, only small amounts of the drug are detectable in plasma after 8 hours. The extended-release tablets of acetaminophen release the drug for up to 8 hours, but in vitro data indicate that at least 95% of the dose is released within 5 hours.
Following rectal administration of acetaminophen, there is considerable variation in peak plasma concentrations attained, and time to reach peak plasma concentrations is substantially longer than after oral administration.
In breast milk peak concentrations of 10 to 15 ug per mL (66.2 to 99.3 micromoles/L) have been measured 1 to 2 hours following maternal ingestion of a single 650-mg dose.
Acetaminophen is rapidly and uniformly distributed into most body tissues. About 25% of acetaminophen in blood is bound to plasma proteins.
Acetaminophen is excreted in urine principally as acetaminophen glucuronide with small amounts of acetaminophen sulfate and mercaptate and unchanged drug. Approximately 85% of a dose of acetaminophen is excreted in urine as free and conjugated acetaminophen within 24 hours after ingestion. Administration of acetaminophen to patients with moderate to severe renal impairment may result in accumulation of acetaminophen conjugates.
/Acetaminophen/ crosses the placenta.
High carbohydrate meals reduced GI absorption rates ... in humans. Possible mechanism may be reaction of drug with pectin, present in some carbohydrate meals. As acetaminophen is absorbed from stomach as well as small intestine, changes in gastric emptying should not greatly alter absorption rate.
Hemodialysis: 120 mL per minute (for unmetabolized drug); metabolites are also cleared rapidly. Hemoperfusion: 200 mL per min. Peritoneal dialysis
The elimination rate and plasma clearance of paracetamol are both significantly reduced in individuals aged 65 years or over.
/Acetaminophen/ distributes uniformly throughout most body fluid and has a volume of distribution of approximately 0.75-1 L/kg.
Acetaminophen (APAP) is a popular analgesic. In the present study, /the authors/ characterized the pharmacokinetics and pharmacodynamics of APAP in the Japanese. Five healthy volunteers were administered 1000 mg of APAP orally. Five patients with chronic pain were administered the optimal oral dose of APAP ranging from 600 to 1000 mg to allow for an adequate analgesic effect. Plasma APAP and APAP metabolite concentrations were measured in the volunteers, plasma APAP concentrations and pain scores using a visual analog scale were measured in the patients with chronic pain. Patient data were fitted to a first-order absorption one-compartment model with delayed effects accounted for by an effect compartment. A sigmoid Emax model was used as the pharmacodynamic model. Acetaminophen-cysteine metabolites, which are conjugates of the toxic metabolite N-acetyl-p-benzoquinone-imine, were detected in the plasma at levels lower than 0.2 microg/ml, but no side effects were observed. The pharmacokinetic and pharmacodynamic parameter (mean+/-S.D.) estimates were as follows: clearance, 18.7+/-4.7 L/hr; distribution volume, 30.9+/-6.8 L; absorption rate constant, 2.4+/-1.3 hr(-1); rate constant for the elimination of APAP from the effect compartment, 1.3+/-0.5 hr(-1); maximum pain relief score, 4.6+/-2.2 units; effect compartment concentration at 50% maximum, 2.0+/-1.2 ug/mL; and sigmoid factor, 1.3+/-0.7. These results suggest that these parameters can be used to determine an effective APAP dosage regimen for Japanese patients with chronic pain. [Shinoda S et al; Biol Pharm Bull 30 (1): 157-61 (2007)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that acetaminophen is expected to have very high mobility in soil(SRC). Volatilization of acetaminophen from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Acetaminophen is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.29X10-5 mm Hg(5). Acetaminophen has been categorized as readily biodegradable following acclimation(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 42(SRC), determined from a log Kow of 0.46(2) and a regression-derived equation(3), indicates that acetaminophen is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.4X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Acetaminophen has been categorized as readily biodegradable following acclimation(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetaminophen, which has a vapor pressure of 6.29X10-5 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acetaminophen is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 hrs(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase acetaminophen may be removed from the air by wet or dry deposition(SRC). Acetaminophen does not absorb light at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

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