HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-(Acetyloxy)benzoesäure
ASPIRIN · 2-ACETOXYBENZOIC ACID · ASPRIN · Aspirine · O-ACETYLSALICYLIC ACID · acetylsalicylic · Acetosal · acetylsalicylate
Identifikatoren & physikalische Daten
| CAS No. | 50-78-2 |
|---|---|
| Summenformel | C9H8O4 |
| Durchschnittliche Molmasse | 180,16 g/mol |
| Monoisotopische Masse | 180,04225873 g/mol |
| SMILES | CC(=O)Oc1ccccc1C(=O)O |
| InChIKey | BSYNRYMUTXBXSQ-UHFFFAOYSA-N |
| PubChem CID | 2244 |
| ChEMBL | CHEMBL25 |
| ChEBI | CHEBI:15365 |
| EC No. | 200-064-1 |
| DTXSID | DTXSID5020108 |
| Lokaler Name | 2-(Acetyloxy)benzoesäure |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 63,6 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 212 |
| LogP (Verteilungskoeffizient) | 1.18log Kow = 1.19 |
| Geruch | Odorless, but in moist air it is gradually hydrolyzed and acquires odor of acetic acidOdorless [Note: Develops the vinegar-like odor of acetic acid on contact with moisture]. |
| Dichte | 1.4 (NTP, 1992) - Denser than waterwill sink1.401.4 g/cm³1.35 |
| Color/Form | Monoclinic tablets or needle-like crystalsColorless to white, crystalline powder. |
| Löslichkeit | less than 1 mg/mL at 73 °F (NTP, 1992)101 g sol in: 300 mL water at 25 °C, 100 mL water at 37 °C, 5 mL alcohol, 17 mL chloroform, 10-15 mL etherless sol in anhydrous etherIn water, 4,600 mg/L at 25 °CSolubility in water, g/100ml at 15 °C: 0.25 (poor)(77 °F): 0.3%H2O: 10 mg/mL at 37 °C3.3 g/L (20 ºC) |
| Flammpunkt | 482 °F (NTP, 1992)250 °C |
| Siedepunkt | 284 °F at 760 mmHg (decomposes) (NTP, 1992)140284 °F (decomposes)272.96°C (rough estimate) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes.140 °C |
| Schmelzpunkt | 275 °F (NTP, 1992)138-140135 °C (rapid heating)134-136 °C (lit.) |
| Dampfdruck | 0 mmHg (approx) (NIOSH, 2024)2.52X10-5 mm Hg at 25 °C (calc)Vapor pressure, Pa at 25 °C: ~ 0.004 |
| Physical Description | Acetylsalicylic acid appears as odorless white crystals or crystalline powder with a slightly bitter taste. (NTP, 1992)Odorless, colorless to white, crystal-line powder. [aspirin] [Note: Develops the vinegar-like odor of acetic acid on contact with moisture.]SolidCOLOURLESS-TO-WHITE CRYSTALS OR WHITE CRYSTALLINE POWDER WITH CHARACTERISTIC ODOUR.Odorless, colorless to white, crystal-line powder. |
| Stability/Shelf Life | STABLE IN DRY AIRIN MOIST AIR IT IS GRADUALLY HYDROLYZED INTO SALICYLIC AND ACETIC ACIDSIn aqueous solutions, aspirin is most stable at a pH of 2-3, less stable at a pH of 4-8, and least stable at a pH less than 2 or greater than 8. In a saturated aqueous solution at a pH of 5-7, aspirin is almost completely hydrolyzed within 1 week at 25 °C. |
| Brechungsindex | 1.4500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | crystalline |
| Farbe | white |
| pKa (Säurekonstante) | 3.5(at 25℃) |
| Biologische Quelle | synthetic |
| Merck | 14,851 |
| BRN | 779271 |
| Henry-Konstante | 7.6×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| BCS Class | 3 |
| Stabilität | Stable. Keep dry. Incompatible with strong oxidizing agents, strong bases, strong acids, various other compounds such as iodides, iron salts, quinine salts, etc. |
| Kosmetik-Inhaltsstoffe Funktionen | EXFOLIATING |
| InChI | 1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12) |
| InChIKey | BSYNRYMUTXBXSQ-UHFFFAOYSA-N |
| SMILES | CC(=O)Oc1ccccc1C(O)=O |
| LogP (Verteilungskoeffizient) | 1.190 |
| CAS Datenbank | 50-78-2(CAS DataBase Reference) |
| NIST chemische Informationen | Benzoic acid, 2-(acetyloxy)-(50-78-2) |
| EPA chemische Informationen | Aspirin (50-78-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.3% (1 of 315) of reports.WarningH302 (95.6%): Harmful if swallowed [Warning Acute toxicity, oral]H315 (20.6%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (22.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (20%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 315 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 315 reports by companies.There are 22 notifications provided by 314 of 315 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Benzoic acid, 2-(acetyloxy)-Hazard Traits - Developmental ToxicityReproductive ToxicityAuthoritative List - Prop 65Report - regardless of intended function of ingredient in the productStatus: Active Update: 02-04-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/10841Status: Active Update: 27-03-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/7490Acetylsalicylic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzoic acid, 2-(acetyloxy)-: Environment tier I assessmentIMAP assessments - Benzoic acid, 2-(acetyloxy)-: Human health tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | SLIGHT WHEN EXPOSED TO HEAT OR FLAME |
| Gesundheitsgefahren | Excerpt from NIOSH Pocket Guide for Acetylsalicylic acid:Exposure Routes: Inhalation, ingestion, skin and/or eye contactSymptoms: Irritation eyes, skin, upper respiratory systemincreased blood clotting timenausea, vomitingliver, kidney injuryTarget Organs: Eyes, skin, respiratory system, blood, liver, kidneys (NIOSH, 2024) |
| Gefahrenübersicht | Aspirin poisoning was one of the leading causes of accidental death in children until child-proof bottles were developedAfter ingestion, causes stimulation of respiratory center in brain and metabolic acidosisProlongs prothrombin time and complicated by cerebral and pulmonary edema1 aspirin tablet = 325-650 mg acetylsalicylic acid1 teaspoon concentrated oil of wintergreen = 5 g of methyl salicylate (equivalent to 7.5 g of acetylsalicylic acid)Acute ingestion of 150-200 mg/kg aspirin = mild intoxicationAcute ingestion of 300-500 mg/kg aspirin = severe intoxication[Olson, p. 410-11] TLV Basis = Bleeding and respiratory sensitization. An oral dose of 30mg/person of ASA (0.45 mg/kg per day) given daily for 3 weeks resulted in a significant prolongation of bleeding time (1.6 times control values) . . . ASA is a known respiratory and systemic allergen in humans, which may result in an anaphylactic phenomenon known as aspirin-exacerbated respiratory disease (AERD). It can occur at oral doses as low as 81 mg daily. [ACGIH TLVs and BEIs] |
| Reaktive Gruppe | Acids, CarboxylicEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Special Reports | International Programme on Chemical SafetyPoisons Information Monograph: Acetylsalicylic Acid (PIM 006) (1991) Available from http://www.inchem.org/pages/pims.html as of March 10, 2008 |
| OSHA Standards | Vacated 1989 OSHA PEL TWA 5 mg/cu m is still enforced in some states. |
| Reactivity Profile | The active ingredient in common aspirin. Incompatible with oxidizers and strong acids. Also incompatible with strong bases. May react with water or nucleophiles (e.g. amines and hydroxy groups). May also react with acetanilide, amidopyrine, phenazone, hexamine, iron salts, phenobarbitone sodium, quinine salts, potassium and sodium iodides, alkali hydroxides, carbonates, stearates and paracetanol. (NTP, 1992) |
| Chemical Dangers | The solution in water is a weak acid. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)(General first aid procedures)Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.Skin: Soap wash - If this chemical contacts the skin, wash the contaminated skin with soap and water.Breathing: Respiratory supportSwallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately. |
| Sichere Lagerung | Well closed. |
| Lagerbedingungen | Chewable aspirin tablets containing 81 mg of the drug should be stored in child-resistant containers holding not more than 36 tablets each in order to limit the potential toxicity associated with accidental ingestion in children. Aspirin suppositories should be stored at 2-15 °C. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should store this material under ambient temperatures and protect it from moisture. (NTP, 1992) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Contact lenses should not be worn when working with this chemical.The worker should immediately wash the skin when it becomes contaminated.Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust. |
| Körperbelastung | Acetylsalicylic acid and the acetylsalicylate ion were detected in the breast milk of nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestion(1). |
| Wechselwirkungen | Prolonged concurrent use of acetaminophen with a salicylate is not recommended because chronic, high-dose administration of the combined analgesics (1.35 g daily, or cumulative ingestion of 1 kg annually, for 3 years or longer) significantly increases the risk of analgesic nephropathy, renal papillary necrosis, end-stage renal disease, and cancer of the kidney or urinary bladderalso, recommended that for short-term use the combined dose of acetaminophen plus a salicylate not exceed that recommended for acetaminophen or a salicylate given individually. /Salicylates/The possibility should be considered that additive or multiple effects leading to impaired blood clotting and/or increased risk of bleeding may occur if a salicylate, especially aspirin, is used concurrently with any medication having a significant potential for causing hypoprothrombinemia, thrombocytopenia, or gastrointestinal ulceration or hemorrhage.Aspirin may decrease the bioavailability of many nonsteroidal anti-inflammatory drugs (NSAIDs), including diflunisal, fenoprofen, indomethacin, meclofenamate, piroxicam (up to 80% of the usual plasma concentration), and the active sulfide metabolite of sulindacaspirin has also been shown to decrease the protein binding and increase the plasma clearance of ketoprofen, and to decrease the formation and excretion of ketoprofen conjugates. Concurrent use of other NSAIDs with aspirin may also increase the risk of bleeding at sites other than the gastrointestinal tract because of additive inhibition of platelet aggregation.Concurrent use of these medications /alcohol or other nonsteroidal anti-inflammatory drugs (NSAIDs)/ with a salicylate may increase the risk of gastrointestinal side effects, including ulceration and gastrointestinal blood lossalso, concurrent use of a salicylate with an NSAID may increase the risk of severe gastrointestinal side effects without providing additional symptomatic relief and is therefore not recommended. /Salicylate/For more Interactions (Complete) data for ACETYLSALICYLIC ACID (21 total), please visit the HSDB record page. |
| Zielorgane | Eyes, skin, respiratory system, blood, liver, kidneys |
| Gesundheitliche Auswirkungen | Might increase the risk of gastrointestinal bleedinglarge doses of salicylate, a metabolite of aspirin, have been proposed to cause tinnitusReye's syndrome, a severe illness characterized by acute encephalopathy and fatty liver, can occur when children or adolescents are given aspirin for a fever or other illnesses or infections. [Wikipedia] |
| Hepatotoxicity | Patients on long term, moderate-to-high dose aspirin therapy frequently have elevations in serum ALT levels. With high doses, ALT elevations are common and can be marked and associated with mild increases in alkaline phosphatase and bilirubin. The more dramatic examples of aspirin hepatotoxicity usually occur with doses of 1,800 to 3,200 mg daily (>100 mg/kg) and with salicylate levels of greater than 25 mg/dL, but mild-to-moderate ALT elevations occur with even lower doses and lower serum levels. These abnormalities resolve rapidly with discontinuation of aspirin, but instances of resolution despite continuation of aspirin in the same or lower doses (adaptation) have also been described. The hepatotoxicity of aspirin is usually mild and asymptomatic, although with higher doses symptoms of nausea, anorexia and abdominal pain and even encephalopathy with signs of hepatic dysfunction (hyperammonemia and coagulopathy) can occur. Bilirubin elevations are usually mild or absent. Mild eosinophilia may accompany the enzyme elevations, but rash, fever and other allergic manifestations are rare. Liver biopsy histology generally shows minimal injury despite the height of the enzyme elevationselectron microscopy may reveal fat and mitochondrial abnormalities. Aspirin can often be continued in lower doses safely.Likelihood score: A[HD] (well known cause of clinically apparent liver injury when given in high doses). |
| Ökotoxizitätswerte | LC50Species: Daphnia magna (Water flea, <24 hr neonate)Conditions: freshwater, static, 21 °C, pH 7.6Concentration: 8.15 mM for 24 hrSpecies: Daphnia pulex (Water flea, <24 hr)Conditions: freshwater, static, 20 °C, pH 7.6Concentration: 2.00 mM for 24 hrSpecies: Artemia salina (Brine shrimp, age 2-3 instar larva)Conditions: saltwater, static, salinity 35 pptConcentration: 2120 umol/L for 24 hrSpecies: Streptocephalus proboscideus (Fairy shrimp, age 2-3 instar larva)Conditions: saltwater, static, 25 °C, salinity 15 pptConcentration: 988 umol/L for 24 hrFor more Ecotoxicity Values (Complete) data for ACETYLSALICYLIC ACID (6 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 1.19(2) and a regression-derived equation(3), indicates that acetylsalicylic acid is expected to have high mobility in soil(SRC). The pKa of acetylsalicylic acid is 3.49(4), indicating that this compound will almost entirely exist in anion form in the environment and anions generally do not adsorb as strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of acetylsalicylic acid from moist soil surfaces will not be an important fate process(SRC) since anions do not volatilize. Acetylsalicylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.5X10-5 mm Hg(6). No biodegradation studies were located for acetylsalicylic acid in soil(SRC, 2008)however, acetylsalicylic acid was classified as readily biodegradable in screening tests(7,8). An aqueous hydrolysis half-life of 6.3 days at pH 7.4 and 17 °C(9), suggests hydrolysis may occur in moist soils(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 100(SRC), determined from a log Kow of 1.19(2) and a regression-derived equation(3), indicates that acetylsalicylic acid is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 3.49(4) indicates acetylsalicylic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. 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). A hydrolysis half-life of 6.3 days at pH 7.4 and 17 °C was calculated for acetylsalicylic acid(7). No biodegradation studies were located for acetylsalicylic acid in water(SRC, 2008)however, acetylsalicylic acid was classified as readily biodegradable in screening tests(8,9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), acetylsalicylic acid, which has a vapor pressure of 2.5X10-5 mm Hg at 25 °C(2) is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase acetylsalicylic acid 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 12 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase acetylsalicylic acid may be removed from the air by wet or dry deposition(SRC). Acetylsalicylic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| Unerwünschte Wirkungen | Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.ACGIH Carcinogen - Not Classifiable. |
| Expositionspfade | The substance can be absorbed into the body by inhalation and by ingestion.inhalation, ingestion, skin and/or eye contactAbsorption is generally rapid and complete following oral administration but may vary according to specific salicylate used, dosage form, and other factors such as tablet dissolution rate and gastric or intraluminal pH. |
| Milk Concentrations | EXPERIMENTAL: Acetylsalicylic acid and the acetylsalicylate ion were detected in the breast milk of nursing mothers within 1 hour of aspirin (acetylsalicylic acid) ingestion(1).Peak salicylate concentrations of 173 to 483 ug/mL have been measured in /breast milk/ 5 to 8 hours after maternal ingestion of a single 650 mg dose /of aspirin/. |
| Toxizitätsübersicht | IDENTIFICATION: Acetylsalicylic acid is colorless or white crystals or white crystalline powder or granulesodorless or almost odorless with a slight acid taste. It is soluble in water. Indications: It is used as an analgesic for the treatment of mild to moderate pain, as an anti-inflammatory agent for the treatment of soft tissue and joint inflammation, and as an antipyretic drug. In low doses salicylate is used for the prevention of thrombosis. HUMAN EXPOSURE: The toxic effects of salicylate are complex. The following appear to be the principal primary effects of salicylate in overdose: Stimulation of the respiratory centerinhibition of citric acid cycle (carbohydrate metabolism)stimulation of lipid metabolisminhibition of amino acid metabolismand uncoupling of oxidative phosphorylation. Respiratory alkalosis, metabolic acidosis, water and electrolyte loss occur as the principal secondary consequences of salicylate intoxication. Central nervous system toxicity (including tinnitus, hearing-loss, convulsions and coma), hypoprothrombinemia and non-cardiogenic pulmonary edema may also occur, though for some the mechanism remains uncertain. Target organs: The target organs are: all tissues (whose cellular metabolism is affected), but in particular the liver, kidneys, lungs and the VIIIth cranial nerve. Summary of clinical effects: the following are symptoms of intoxication: Nausea, vomiting, epigastric discomfort, gastrointestinal bleeding (typically with chronic and rarely with acute intoxication)tachypnea and hyperpneatinnitus, deafness, sweating, vasodilatation, hyperpyrexia (rare), dehydrationirritability, tremor, blurring of vision, subconjunctival haemorrhages. The following are the effects on blood glucose: hyper- or hypoglycemiaeffects on blood: hypoprothrombinemiaeffects on liver: increased serum aminotransferase activities (SGOT and SGPT). Non-cardiogenic pulmonary edemaconfusion, delirium, stupor, asterixis, coma, cerebral edeThe analgesic, antipyretic, and anti-inflammatory effects of acetylsalicylic acid are due to actions by both the acetyl and the salicylate portions of the intact molecule as well as by the active salicylate metabolite. Acetylsalicylic acid directly and irreversibly inhibits the activity of both types of cyclooxygenase (COX-1 and COX-2) to decrease the formation of precursors of prostaglandins and thromboxanes from arachidonic acid. This makes acetylsalicylic acid different from other NSAIDS (such as diclofenac and ibuprofen) which are reversible inhibitors. Salicylate may competitively inhibit prostaglandin formation. Acetylsalicylic acid's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanismsthe therapeutic effects are not due to pituitary-adrenal stimulation. The platelet aggregation-inhibiting effect of acetylsalicylic acid specifically involves the compound's ability to act as an acetyl donor to cyclooxygenasethe nonacetylated salicylates have no clinically significant effect on platelet aggregation. Irreversible acetylation renders cyclooxygenase inactive, thereby preventing the formation of the aggregating agent thromboxane A2 in platelets. Since platelets lack the ability to synthesize new proteins, the effects persist for the life of the exposed platelets (7-10 days). Acetylsalicylic acid may also inhibit production of the platelet aggregation inhibitor, prostacyclin (prostaglandin I2), by blood vessel endothelial cellshowever, inhibition prostacyclin production is not permanent as endothelial cells can produce more cyclooxygenase to replace the non-functional enzyme. |
| Ökotoxizitätsauszüge | /BIRDS and MAMMALS/ The impact of acetyl salicylic add (ASA) on reproductive performance during periods of heat stress was studied in Japanese quail (Coturnix coturnix japonica). During a season when daily high temperatures averaged between 34 and 40 degrees C, four treatments each containing four replicates of five males and five females were given 0, 0.5, 1.0, or 1.5 g/L ASA in drinking water from 34 to 45 wk of age. At 39 wk of age control quail were lighter than quail fed ASA. Quail receiving 1.5 g/L ASA exhibited increased fertility, hatchability, and egg production and decreased late dead and total embryonic mortality. Early dead embryos, pips, chick weight, and egg weight were not different among treatments. The lumen of uterovaginal junction sperm host glands (UVJSHG) from control quail was apparently devoid of spermatozoa, whereas quail receiving 1.5 g/L ASA had the greatest apparent accumulation of spermatozoa. Control caudal infundibulum host glands (CPOI) were devoid of spermatozoa in contrast with CPOI from quail receiving ASA. Results show that UVJSHG lumens from quail receiving 1.5 g/L ASA had larger inside diameters than other treatment groups. However, the CPOI inside diameter and the outside diameters of both UVJSHG and CPOI were not affected by ASA. Adding 1.5 g/L ASA to the drinking water of quail under heat stress improved body weight, fertility, hatchability, embryonic mortality, egg production, egg specific gravity, and sperm storage capacity./AQUATIC SPECIES/ Metabolic products are often more toxic than their pharmacological parent compounds. Therefore, the acute and chronic effects of the main metabolites--salicylic acid (SAL), gentisic acid (GEN), and o-hydroxyhippuric acid (HDP)--of acetylsalicylic acid (ASA), the active ingredient in Aspirin and many other pharmaceuticals, were assessed using standard (Daphnia magna) and autochthonous (Daphnia longispina) cladocerans. The sequence of decreasing levels of acute and chronic toxicity of ASA metabolites to daphnids was GEN > SAL > HDP. HDP did not present acute toxicity, but chronic exposures enabled the production of abnormal neonates and, in particular, egg abortion. Thus, reproduction was the end point most susceptible to HDP. On the other hand, SAL and GEN induced changes in the normal patterns of reproduction and growth of both species. In general, D. longispina was more sensitive than was D. magna, although the population growth of the autochthonous species was superior under SAL exposures than that of the standard test species. Although the concentrations that were determined to have a toxic effect were above the levels detected in aquatic environmental samples, exposure to low levels of pharmacologically active substances for a duration longer than the test period may induce changes in nontarget organisms./PLANTS/ PHYTOTOXICITY: CHROMOSOMAL ABERRATIONS & ALTERATIONS IN ROOT CELLS OF BROAD BEAN PLANTS TREATED WITH ACETYLSALICYLIC ACID (1.0 GRAIN). |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 5 mg/m3 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1851 |
| Zollcode | 29182210 |
| RTECS-Nr. | VO0700000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | LD50 orally in mice, rats: 1.1, 1.5 g/kg (Hart) |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36/37/39 |
| Gefahrenklasse | 6.1Acute Tox. 4 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 50-78-2(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Acetylsalicylsäure bildet farblose, glänzende Nadeln oder Blättchen mit säuerlichen Geschmack. Sie ist wenig löslich in Wasser und Diethylether. Die Substanz wirkt stark antipyretisch, analgetisch, antiphlogistisch und hemmt die Thrombozytenaggregation. D
Beschreibung
Acetylsalicylic acid is a white crystalline powder commonly known by its common name as aspirin or ASA. Aspirin is the most widely used medication in the world.
History
Willow leaves and bark contain salicin which is the active ingredient that dulls pain. Most histories of aspirin include four-thousand-year-old Sumerian tablets that mention willow as pain relief. It was also used by the ancient Chinese and Greeks.In the eighteenth century, Edward Stone, an English vicar used dried willow bark for five years to treat fevers. Drying it concentrates the salicin. Then in eighteen-twenty-six, Italian researchers extracted salicin from willow bark and two years later, German pharmacologist Joseph Buchner, professor of pharmacy at Munich University, Germany, succeeds in extracting the active ingredient from willow, producing bitter tasting yellow crystals that he names salicin (for willow in Latin).In 1876, the first rigorous clinical trial of salicin finds that it induces remission of fever and joint inflammation in patients with rheumatism. While working for pharmaceutical company Bayer, German chemist Felix Hoffmann finds that adding an acetyl group to salicylic acid reduces its irritant properties and Bayer patents the process and named Acetylsalicylic acid as Aspirin.
Verwenden
Acetylsalicylic acid is the prototypical analgesic used in the treatment of mild to moderate pain. Acts as an inhibitor of cyclooxygenase which results in the inhibition of the biosynthesis of prostaglandins. Acetylsalicylic acid also inhibits platelet aggregation and is used in the prevention of arterial and venous thrombosis. Along with sodium salicylate (sc-3520), aspirin has been shown to block the long terminal repeat from the human immunodeficiency virus and the Ig κ enhancer from NFκB dependent transcription.