Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
2,3-디메르캅토-1-프로판올
2,3-디메르캅토-1-프로판올 · BAL · DIMERCAPROL · 2,3-DIMERCAPTOPROPAN-1-OL · BACS · BAL1 · Parp9 · Panobal
식별자 및 물리적 특성
| CAS No. | 59-52-9 |
|---|---|
| 분자식 | C3H8OS2 |
| 평균 분자량 | 124.23 g/mol |
| 단동위원소 질량 | 124.00165688 g/mol |
| SMILES | OCC(S)CS |
| InChIKey | WQABCVAJNWAXTE-UHFFFAOYSA-N |
| PubChem CID | 3080 |
| ChEMBL | CHEMBL1597 |
| ChEBI | CHEBI:64198 |
| EC No. | 200-433-7 |
| DTXSID | DTXSID5040461 |
| 현지명 | 2,3-디메르캅토-1-프로판올 |
화학 및 물리적 성질
| XLogP | 0.2 |
|---|---|
| 극성 표면적 | 22.2 |
| 수소 결합 공여자 수 | 3 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 6 |
| 형식 전하 | 0 |
| 복잡도 | 32 |
| 물질 분류 | Other Classes -> Sulfur Compounds (Alcohols) |
| SpringerMaterials Properties | Boiling point |
| 냄새 | Pungent offensive odor of mercaptans자극적인 냄새 |
| 밀도 | 1.2463 at 68 °F (NTP, 1992) - Denser than waterwill sink1.2385 at 25 °C/4 °C1.239 g/mL at 25 °C(lit.) |
| Color/Form | Viscous oily liquidColorless |
| 용해도 | 10 to 50 mg/mL at 68 °F (NTP, 1992)Soluble in ether, ethanolslightly soluble in chloroformSoluble in vegetable oilsSolubility in water: 8.7 g/100 mL87g/l(느린 분해) |
| 인화점 | greater than 235 °F (NTP, 1992)Flash Point > 235 °F>230 °F |
| Human Drugs | FDA approved drugs -> Active ingredientAntidotes and other substances used in poisonings > Specific |
| 끓는 점 | 248 °F at 15 mmHg (NTP, 1992)BP: 68-69 °C at 0.0001 mm Hg83 °C at 0.8 mm HgBP: 120 °C at 15 mm Hg120 °C15 mm Hg(lit.) |
| 녹는점 | < 25 °C77 °C |
| 증기 밀도 | 4.3 (NTP, 1992) - Heavier than airwill sink (Relative to Air)4.3 (Air = 1) |
| 증기압 | 4.92 mmHg at 77 °F (NTP, 1992)4.92 [mmHg]VP: 1.9 mm Hg at 80 °C40 mm Hg at 140 °C.7.4 hPa (100 °C) |
| 굴절률 | n20/D 1.573(lit.) |
| 저장 조건 | Store at +2°C to +8°C. |
| pKa(산도 계수) | 9.00±0.25(Predicted) |
| 물리적 상태 | 액체 |
| 색상 | 무색투명~미황색 |
| pH | 5.0-6.5 (H2O, 20℃)(saturated solution) |
| 생물학적 소스 | rabbit |
| 용해도 | 87g/L(25℃) |
| Merck | 14,3209 |
| BRN | 1732058 |
| 헨리 상수 | 1.1×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제, 많은 금속과 호환되지 않습니다. |
| InChI | 1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2 |
| InChIKey | WQABCVAJNWAXTE-UHFFFAOYSA-N |
| SMILES | OCC(S)CS |
| NIST | Dimercaprol(59-52-9) |
| EPA | 2,3-Dimercaptopropanol (59-52-9) |
화학적 성질
colourless oily liquid with a typically offensive mercaptan smell
안전 및 규제
| GHS 분류 | DangerH301 (94.1%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 51 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Chemical: 1-Propanol, 2,3-dimercapto-2,3-Dimercapto-1-propanol: Does not have an individual approval but may be used under an appropriate group standard |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | This chemical is probably combustible. (NTP, 1992) |
| 건강 유해성 | SYMPTOMS: Symptoms of exposure to this chemical may include a warm feeling, tingling sensations in the nose, mouth and skinnausea, vomiting, restlessness, weakness, rapid pulse, rise in blood pressure, tremors, convulsions, tachycardia, headache, feeling of constriction or pain in the throat, chest or handsconjunctivitis, lachrymation, rhinorrhea, salivation, sweating of the forehead, hands, etc.abdominal pain and anxiety. |
| 유해성 요약 | Contact with eyes can cause severe lacrimation for an hour or two with no permanent damage[HSDB] A lachrymator[CAMEO] An irritantHarmful if swallowedReproductive effects in animal experiments[MSDSonline] |
| FDA 요건 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including dimercaprol, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| 반응성 그룹 | Alcohols and Polyols |
| Reactivity Profile | 2,3-DIMERCAPTO-1-PROPANOL forms highly stable chelates with a variety of metal ions. (NTP, 1992) Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. |
| Air and Water Reactions | Moderately soluble in water with decomposition [Hawley]. |
| Hazard Classes and Categories | Acute Tox. 3 (94.1%) |
| Skin, Eye, and Respiratory Irritations | Dimercaprol may cause eye irritation. |
| 소화 | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| 응급 처치 | 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. |
| 비화재 누출 대응 | SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated 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. |
| 처리 방법 | SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| 상호 작용 | ...GUINEA PIGS ACUTELY POISONED BY IM INJECTION OF TELLURIUM OXIDE SHOWED SEVERE LESIONS OF KIDNEYS & LIVER & HIGHER MORTALITY RATE WHEN RECEIVING BAL...Dimercaprol forms a toxic complex with iron, cadmium, selenium, or uranium. Iron therapy should not be given concurrently with dimercaprol, and it has been suggested that iron therapy be deferred until at least 24 hours after the last dose of dimercaprol.Dimercaprol is a compound used in the treatment of mercury intoxication, however with low therapeutic efficacy. It is assumed that dimercaprol acts by reactivating target sulfhydryl-containing proteins. In the present investigation we studied the inhibitory effect of mercuric chloride treatment (3 days with 2.3 or 4.6 mg/kg HgCl2, sc) in mice on cerebral. renal and hepatic delta-aminolevulinate dehydratase (ALA-D) activity, and a possible reversal of the effect of mercury by dimercaprol (0.25 mmol/kg, 24 hr after the last mercury injection). Mercuric chloride did not inhibit cerebral delta-aminolevulinate dehydratase at the doses injected. Dimercaprol treatment did not restore the normal enzyme activity of the liver after the 25% inhibition caused by 4.6 mg/kg HgCl2. In the kidney, dimercaprol enhanced the inhibitory effect of 4.6 mg/kg mercuric chloride (from 35% after mercury treatment alone to 65% after mercury plus dimercaprol treatment). Mercury content increased in kidney after exposure to 2.3 or 4.6 mg/kg and the levels attained were higher than in any other organ. Mercury accumulated in liver only after exposure to 4.6 mg/kg HgCl2. and dimercaprol further increased mercury deposition. Dimercaprol treatment also increased the levels of mercury in brain of animals exposed to 4.6 mg/kg HgCl2. The enzymes from all sources presented similar sensitivity to the combined effect of HgCl2 and dimercaprol in vitro. In the absence of preincubation, 0-500 uM dimercaprol potentiated the inhibitory effect of HgCl2 on delta-aminolevulinate dehydratase activity. In the presence of preincubation, and 100 and 250 uM dimercaprol enhanced delta-aminolevulinate dehydratase sensitivity to mercury, whereas 500 uM dimercaprol partially protected the enzyme from mercury inhibition. Dimercaprol (500 uM) inhibited renal and hepatic delta-aminolevulinate dehydratase when preincubated with the enzymes. These data suggested that the dimercaprol-Hg complex may have a more toxic effect on delta-aminolevulinate dehydratase activity than Hg2+. Furthermore, the present data show that dimercaprol did not act by reactivating mercury-inhibited sulfhydryl-containing delta-aminolevulinate dehydratase, and that indeed it may have an inhibitory effect per se depending on the tissue.Dimercaprol decreases insulin effectiveness by reducing disulfide bridges. |
| Hepatotoxicity | In clinical trials conducted in children with Wilson disease, serum aminotransferase levels generally improved or were stable during treatment with dimercaprol. There have been no clinical reports of acute liver injury with jaundice attributed to dimercaprol. Patients with Wilson disease typically have mild-to-moderate serum aminotransferase elevations and may have signs and symptoms of cirrhosis. Improvement in liver injury in Wilson disease typically requires months to years of treatment. The apparent lack of hepatotoxicity of dimercaprol may be due to the infrequency of its use, the typically short courses of therapy and the prominence of other side effects that limit its more prolonged administration. |
| 유해 작용 | Reproductive Toxin - A chemical that is toxic to the reproductive system, including defects in the progeny and injury to male or female reproductive function. Reproductive toxicity includes developmental effects. See Guidelines for Reproductive Toxicity Risk Assessment.There are many adverse effects associated with the chelating agent dimercaprol. Signs and symptoms appear to depend on dosage and the time between each dose with hypertension, tachycardia, nausea, and vomiting most frequently noted. |
| 독성 요약 | IDENTIFICATION: Dimercaprol is a therapeutic compound developed as an antidote against the vesicant arsenic was gases such as Lewisite. It is clear to slightly yellow liquid with a pungent odor of mercaptan. It is slightly soluble in water and vegetable oils. Arachis or peanut oil is used in pharmaceutical preparations. It is miscible in alcohol, benzyl benzoate, ether, methyl alcogol and other solvents. Dimercaprol is useful in the treatment of arsenic (organic and inorganic), gold and inorganic mercury poisoning. HUMAN EXPOSURE: The main risks are hypertension, tachycardia, cardiovascular collapse, convulsions, excitation, hyperglycemia and hypoglycemia. Special care should be taken in case of oliguria, hypertension and impaired hepatic function when the antidote is administered. The target organs are the kidneys, the cardiovascular and central nervous systems. The clinical effects are nausea, vomiting, headache, burning sensation of the lips, throat, mouth and eyeslacrimation and salivationsweating, rhinorrhea and burning sensation of the penisa feeling of constriction or pain in the throat or chest, muscle pains and spasms and tingling of the skin of the handsabdominal pain, anxiety, nervousness and weakness, uticaria and hyperpyrexia. Pain and sterile abscesses can result. Irritation of the skin and mucous membranes can be observed after local contact. This drug should always be administered as soon as possible by deep IM injection and never by IV or SC routes. Dimercaprol is well tolerated in children. The drug cannot be used in poisonings due to iron, cadmium, tellurium, selenium, vanadium and uranium. It is contraindicated in poisonings due to elemental mercury vapor, because it can further increase the metal in the brain. This drug should not be administered in case of renal and hepatic insufficiency and patients with hypertension. Dermal absorption is possible. Peak concentrations in the blood are obtained 30-60 min after IM injection. Dimercaprol is a lipophilic drug, it penetrates rapidly in intracellular spaces. The highest concentrations are found in the liver, kidneys, brain and small intestine. Glucuronic acid conjugates are excreted by the kidneys. Iron therapy should be given 24 hr or more after the last dose of dimercaprol. It should not be administered at the same time. Breath may smell like odor of a mercaptan. Hemolytic anemia was reported in individuals with G6PD deficiency. In children, dimercaprol may induce a transient reduction in polymorphonuclear leukocytes. ANIMAL STUDIES: In animal studies, the biological half life was short and metabolic degradation and renal excretion is complete within 6-24 hr. In animals a lethal dose of dithiols causes convulsions and severe spasm of the abdominal muscles shortly before death occurs. After injection of sublethal amounts of dimercaprol, the animals become apathetic and develop lacrimation, edema of the conjunctiva, blepharospasms, salivation and vomiting. With increasing doses they develop ataxia, analgesia, muscle tremor, nystagmus, tonic and clonic convulsions and death results during coma. In cats following an IV injection cardiovascular depression as indicated by a fall in systemic and pulmonary artery pressure. After repeated local applications in animals, sensitization dermatitis may develop. Chronic effects in animals include fatty degeneration of the liver and impairment of liver function. In animals, chronic parenteral administration increases white blood cell count by 30%. This drug induced malformations of the skeletal system, growth retardation and increased embryo lethality.There are no antidotes available for dimercaprol. Therefore, if toxicity presents with dimercaprol, cessation of therapy is recommended until the resolution of symptoms. Clinical judgment should be used to determine whether to continue, taper off, or discontinue treatment with dimercaprol. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Dosage exceeding 5 mg/kg will usually be followed by vomiting, convulsions and stupor, beginning within 30 minutes and subsiding within 6 hours following injection/SIGNS AND SYMPTOMS/ In humans, the administration of dimercaprol produces a number of side effects that usually are more alarming than serious. Reactions to dimercaprol occur in approximately 50% of subjects receiving 5 mg/kg intramuscularly. The effects of repeated administration of this dose are not cumulative if an interval of at least 4 hours elapses between injections. One of the most consistent responses to dimercaprol is a rise in systolic and diastolic arterial pressures, accompanied by tachycardia. The rise in pressure may be as great as 50 mmHg in response to the second of two doses (5 mg/kg) given 2 hours apart. The pressure rises immediately but returns to normal within 2 hours./SIGNS AND SYMPTOMS/ CONTACT...WITH HUMAN EYE CAUSES VERY SEVERE, PERSISTENT STINGING SENSATION, BLEPHAROSPASM, LACRIMATION, & PHOTOPHOBIA FOR AN HOUR OR TWO, BUT NO DAMAGE TO EYE./SIGNS AND SYMPTOMS/ The major causes of death are usually related to the cause of poisoning. But Dimercaprol could cause convulsions and comairreversible cardiovascular collapseacidosis and hydroelectrolytic disturbances, renal failureand secondary consequences of hypertension such as brain injury or cardiac failure.For more Human Toxicity Excerpts (Complete) data for Dimercaprol (7 total), please visit the HSDB record page. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)DimercaprolvNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ After injection of sublethal amounts of dimercaprol, the animals become apathetic and develop lacrimation, edema of the conjunctiva, blepharospasm, salivation, and vomiting. With increasing doses, they develop ataxia, analgesia, tachypnea, and hyper-excitability. Nystagmus and muscle tremor develop, and tonic and clonic convulsions occur at the final stages. Death occurs during coma./LABORATORY ANIMALS: Acute Exposure/ The most important systemic acute toxic effect of dimercaprol, ... is cardiovascular depression as judged by a fall in systemic and pulmonary artery pressure following intravenous injection in cats./LABORATORY ANIMALS: Acute Exposure/ After im injection into sheep...lameness & stiffness of injected leg, with knuckling of fetlock & spreading of claws, occurred. With toxic doses, severe systemic symptoms later became apparent, animals being unable to stand, lying on their briskets with legs spread out, & showing periodic, generalized clonic convulsions./LABORATORY ANIMALS: Acute Exposure/ In most experimental animals...accumulation of fluid in serous cavities or lungs and congestion of viscera have been only post-mortem findings.For more Non-Human Toxicity Excerpts (Complete) data for Dimercaprol (8 total), please visit the HSDB record page. |
| Populations at Special Risk | Dimercaprol has been reported to induce hemolysis (which may be severe) in individuals with glucose-6-phosphate dehydrogenase deficiency. Therefore, high-risk individuals should be screened for this deficiency, and susceptible patients should be monitored for hemolysis during therapy with dimercaprol.Dimercaprol is contraindicated in patients with impaired hepatic function, except those with postarsenical jaundice. Dimercaprol also is contraindicated in individuals with known hypersensitivity to peanuts, since the injection is only available as a solution in peanut oil.BAL in Oil Ampules is formulated with peanut oil. Peanut oil may cause allergic reactions in some individuals. Physicians should use caution in prescribing BAL in Oil Ampules for peanut-sensitive patients. Medication and equipment necessary to treat allergic reactions should be available if the product is administered to peanut-allergic patients |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,112 workers (572 of these were female) were potentially exposed to dimercaprol in the US(1). |
| Antidote and Emergency Treatment | /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/ |
| Non-Human Toxicity Values | LD50 Mouse ip 125 mg/kg (approx)LD50 Rat ip 140 mg/kg (approx)LD50 Rat intramuscular 105 mg/kg (approx) |
| 수질 위해 등급(WGK) | 3 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | UB2625000 |
| 운송 번호(UN) | UN 2810 6.1/PG 3 |
| 독성 | LD50 i.m. in rats: 86.7 mg/kg (Zvirblis, Ellin) |
| 관세 코드 | 29309070 |
| 위험 문구(R) | 22-36/37/38-36/38 |
| 위험 표시 | Xn,Xi |
| 안전 문구(S) | 26-36-24/25-23 |
| 포장분류 | III |
| 위험 등급 | 6.1Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| F 고인화성물질 | 8-9-13-23 |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 유해 물질 데이터 | 59-52-9(Hazardous Substances Data) |
용도
개요
Dimercaprol (INN) or British anti - Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II . It was developed secretly as an antidote for lewisite, the now - obsolete arsenic - based chemical warfare agent . Today, it is used medically in treatment of arsenic, mercury , gold, lead, antimony, and other toxic metal poisoning . In addition , it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper.
용도
2,3-Dimercapto-1-propanol has been used in synthesizing novel (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives, which are potent tyrosinase inhibitors. It can also be considered for developing new drugs against AIDS due to its ability to inhibit HIV-1 tat activity.
일반 설명
Clear colorless viscous liquid with a pungent offensive odor of mercaptans. Used as a medicine and an antidote to the chemical warfare agent LEWISITE.