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Dimethyl Sulfoxide
ジメチルスルホキシド · ジメチルスルホキシド [流動パラフィン試験用] · ジメチルスルホキシド [吸光分析用] · ヒアズール · デマソルブ · メチルスルホキシド · ドリクール · デメソー
識別子と物理属性
| CAS No. | 67-68-5 |
|---|---|
| 分子式 | C2H6OS |
| 平均分子量 | 78.14 g/mol |
| 単同位体質量 | 78.01393581 g/mol |
| SMILES | CS(C)=O |
| InChIKey | IAZDPXIOMUYVGZ-UHFFFAOYSA-N |
| PubChem CID | 679 |
| ChEMBL | CHEMBL504 |
| ChEBI | CHEBI:28262 |
| EC No. | 200-664-3 |
| DTXSID | DTXSID2021735 |
| 現地名 | ジメチルスルホキシド |
化学・物理的性質
| XLogP | -0.6 |
|---|---|
| 極性表面積 | 36.3 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 4 |
| 形式電荷 | 0 |
| 複雑度 | 29 |
| 物質分類 | Teratogens |
| 医薬品 | Pharmaceuticals |
| Solvents | Solvents -> Other Solvents |
| SpringerMaterials Properties | Coriolis coupling |
| 香料 | Fragrance Ingredient (Methylsulfinylmethane) -> IFRA transparency List |
| LogP（分配係数） | log Kow = -1.35-1.35 (calculated)-0.85 |
| 臭い | Slightly sulfurous odorDistinctive garlic or oyster-like odorマイルドなニンニク臭 |
| 味 | Slightly bitter taste with sweet after-taste |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 密度 | 1.101 at 68 °F (USCG, 1999) - Denser than waterwill sink1.100 at 20 °C/4 °CRelative density (water = 1): 1.11.087-1.0921.101 @25 °C1.100 g/mL at 20 °C |
| 香味料 | EU Flavoring substances |
| Viscosity | 2.47cP at 20 °C1.95 mm²/s at 20 °C |
| 融点 | 18.4 °C |
| 沸点 | 189 °C(lit.) |
| 蒸気密度 | 2.7 (vs air) |
| 蒸気圧 | 0.42 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.479(lit.) |
| FEMA | 3875 | METHYLSULFINYLMETHANE |
| 引火点 | 192 °F |
| 貯蔵条件 | Store at +5°C to +30°C. |
| 溶解度 | H2O: 混和性 (完全に)水、メタノール、アセトン、エーテル、ベンゼン、クロロホルムに可溶。 |
| pKa（酸解離定数） | 35(at 25℃) |
| 外観・状態 | 液体 (温度依存) |
| 色 | 無色透明 |
| においのタイプ | ニンニクっぽい |
| 由来生物 | synthetic |
| 爆発限界 | 1.8-63.0%(V) |
| 凝固点 | 18.4℃ |
| 比熱容量 | Cp(liquid): 1.96 J/(g·K), at 25℃ |
| Merck | 14,3259 |
| JECFA Number | 507 |
| BRN | 506008 |
| ヘンリー定数 | 9.8×102 mol/(m3Pa) at 25℃, Burkholder et al. (2019) |
| 誘電率 | 41.9(55℃) |
| 安定性 | 安定。酸塩化物、強酸、強力な酸化剤、強力な還元剤、ハロゲン化リン、湿気、銅線 + トリクロロ酢酸など、多くの物質と互換性がありません。 |
| 化粧品成分の機能 | 溶媒 |
| InChI | 1S/C2H6OS/c1-4(2)3/h1-2H3 |
| InChIKey | IAZDPXIOMUYVGZ-UHFFFAOYSA-N |
| SMILES | CS(C)=O |
| LogP（分配係数） | -1.35 |
| 表面張力 | 42.179mN/m at 298.15K |
| CAS データベース | 67-68-5(CAS DataBase Reference) |
| NISTの化学物質情報 | Dimethyl sulfoxide(67-68-5) |
| EPAの化学物質情報 | Dimethyl sulfoxide (67-68-5) |
| Absorption | passes test |
化学的特性
Dimethyl sulfoxide occurs as a colorless, viscous liquid, or as colorless crystals that are miscible with water, alcohol, and ether. The material hasa slightly bitter taste with a sweet aftertaste, and is odorless, or has a slight odor characteristic of dimethyl sulfoxide.Dimethyl sulfoxide is extremely hygroscopic, absorbing up to 70% of its own weight in water with evolution of heat.
化学性质
吸湿性の高い色臭の液体．沸点189℃，融点18.4℃
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 65.1% (611 of 938) of all reports.WarningH315 (28.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 938 reports by companies from 27 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Methane, sulfinylbis-Regulation (EC) No 1831/2003 (amended)Methane, 1,1'-sulfinylbis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Methane, 1,1'-sulfinylbis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 18-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15007Dimethyl sulphoxide: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| その他の安全情報 | IMAP assessments - Methane, sulfinylbis-: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Special Hazards of Combustion Products: Sulfur dioxide, formaldehyde, and methyl mercaptan can form (USCG, 1999)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 87 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with incompatible substances. See Chemical Dangers. |
| 火災の可能性 | Combustible when exposed to heat or flame. |
| 健康有害性 | Slight eye irritation. (USCG, 1999) |
| 有害性の概要 | A skin and eye irritantMay cause CNS depression after inhalation, ingestion, or skin absorption of high dosesLong term use may cause adverse effects to the liver and blood[ICSC] Rats experienced no significant effects after inhalation of 200 mg/m3 (62.8 ppm) for 30 days. After skin absorption, humans may experience garlic odor on the breath, headache, nausea, and dizziness. DMSO enhances the absorption of other drugs. [CHEMINFO] Health effects after inhalation of high concentrations may include headache, dizziness, and sedation. [CAMEO] Dermal doses as high as 1 g/kg per day have been shown to have no significant adverse clinical effects in well-controlled human studies. [AIHA] |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including dimethyl sulfoxide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.Ophthalmic and topical dosage form new animal drugs. Dimethyl sulfoxide. ... Conditions of use in horses and dogs-(1) Amount-(i) Horses. Apply topically two to three times daily in an amount not to exceed 100 mL per day. Total duration of therapy should not exceed 30 days. (ii) Dogs. Apply topically three to four times daily in an amount not to exceed 20 mL per day. Total duration of therapy should not exceed 14 days. (2) Indications for use. To reduce acute swelling due to trauma. (3) Limitations. Do not use in horses intended for human consumption. Federal law restricts this drug to use by or on the order of a licensed veterinarian.To reduce acute swelling due to trauma. (3) Limitations. Do not use in horses intended for human consumption. Federal law restricts this drug to use by or on the order of a licensed veterinarian.Fluocinolone acetonide, dimethyl sulfoxide solution. ... Conditions of use in dogs-(1) Amount-Instill 1 to 2 milliliters into each anal sac following expression of anal sac contents. (2) Indications for use. For the relief of impaction commonly present in apparently normal anal sacs, for the reversal of inflammatory changes associated with abnormal anal sacs, and to counteract the offensive odor of anal sac secretions. (3) Limitations. Federal law restricts this drug to use by or on the order of a licensed veterinarian.Fluocinolone acetonide, dimethyl sulfoxide otic solution. ... Conditions of use in dogs-(1) Amount-Instill 4 to 6 drops (0.2 milliliter) twice daily into the ear canal for a maximum period of 14 days. The total dosage used should not exceed 17 milliliters. (2) Indications for use. For the relief of pruritis and inflammation associated with acute and chronic otitis. (3) Limitations. Federal law restricts this drug to use by or on the order of a licensed veterinarian. |
| 反応性グループ | Sulfonates, Phosphonates, and Thiophosphonates, Organic |
| Special Reports | Jacob SW, Herschler RPharmacology of DMSOCryobiology 23 (1): 14-27 (1986). A wide range of primary pharmacological actions of dimethyl sulfoxide documented in laboratory studiesSwanson BNMedical Rev Clin Basic Pharm 5 (1-2): 1-33 (1985). A review of the medical use of dimethyl sulfoxide.Trice JM, Pinals RSDimethyl Sulfoxide: A Review of its Use in the Rheumatic Disorders. Semin Arthritis Rheum 15 (1): 45-60 (1985). The history, physical/chemical and pharmacological properties, pharmacokinetics, clinical trials, therapeutic uses, side effects, dosage and administration of dimethyl sulfoxide are reviewed. Legal implications and concerns with regard to its use are presented.Jimenez RA, Willkens RFJ Lab Clin Med 100 (4): 489-500 (1982). A review of dimethyl sulfoxide's use in rheumatic diseases.For more Special Reports (Complete) data for DIMETHYL SULFOXIDE (6 total), please visit the HSDB record page. |
| FIFRA 要件 | Residues of dimethyl sulfoxide are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: solvent or cosolvent for formulations used before crop emerges from soil or prior to formation of edible parts of food plants.Dimethyl sulfoxide (DMSO) ... is exempted from the requirement of a tolerance when used as an inert solvent or cosolvent in formulations with the following pesticides when used in accordance with good agricultural practices in or on the following raw agricultural commodities: (a) Carbaryl (1-naphthyl methyl-carbamate) - pea, dry, seedpea, succulent (b) O-O-Diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl) phosphorothioate - pea, dry, seedpea, succulent. |
| Reactivity Profile | DIMETHYL SULFOXIDE decomposes violently on contact with many acyl halides and related compounds such as acetyl chloride, benzenesulfonyl chloride, benzoyl chloride, cyanuric chloride, phosphorus trichloride, phosphorus oxychloride, and thionyl chloride [Chem. Eng. News 35(9):87 (1957)]. |
| 消火 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| 応急処置措置 | Fresh air, rest.Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. Refer for medical attention . |
| 応急処置 | 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. |
| 安全保管 | Separated from incompatible materials and : see Chemical Dangers. Well closed. Cool. Dry. Keep in the dark. Keep in a well-ventilated room. |
| Firefighting Hazards | Special hazards arising from the substance or mixture: Carbon oxides, Sulphur oxides |
| 暴露管理・個人防護 | 50.0 [ppm] |
| 消火手順 | For small (incipient) fires, use media such as "alcohol" foam, dry chemical, or carbon dioxide. For large fires, apply water from as far as possible. Use very large quantities (flooding) of water applied as a mist or spraysolid streams of water may be ineffective. Cool all affected containers with flooding quantities of water.Wear self contained breathing apparatus for fire fighting if necessary.To fight fire use water, foam, alcohol foam, carbon dioxide, dry chemical. |
| 保管条件 | Store away from oxidizing agents, heat, and ignition sources. |
| 清掃方法 | Accidental Release Measures. Personal precaustions, protective equipment and emergency procedure: Avoid breathing vapors, mist or gas. Remove all sources of ignition. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let products enter drains.Methods and materials for containment adn cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal. |
| 非火災時の漏出対応 | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations.This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. |
| 漏出処分 | Remove all ignition sources. Personal protection: protective gloves, protective clothing, safety goggles and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Treatment | In case of accidental oral ingestion, specifc measures should be taken to induce emesis. Additional measures which may be considered are gastric lavage, activated charcoal and force diuresis. (L1712) |
| 相互作用 | Previous studies performed in our laboratory indicated that non-toxic concentrations of peroxynitrite nevertheless commit U937 cells to a rapid necrosis that is however prevented by a survival signaling driven by cytosolic phospholipase A(2)-released arachidonic acid. Toxicity was mediated by concentrations of peroxynitrite resulting in H(2)O(2)-dependent inhibition of arachidonic acid release. The present study shows that U937 cells differentiated to monocytes by prolonged exposure to dimethyl sulfoxide are resistant to peroxynitrite because able to respond with enhanced release of arachidonic acid. An additional important observation was that these cells require more arachidonate than the undifferentiated cells to support the survival signaling. The enhanced arachidonic acid release was not associated with changes in cytosolic phospholipase A(2) expression but was rather dependent on the increased responsiveness of the enzyme to calcium-dependent stimulation as well as on reduced mitochondrial formation of H(2)O(2). The latter event was found to be critical, since differentiated and undifferentiated cells were equally sensitive to peroxynitrite when the accumulation of H(2)O(2) was enhanced via depletion of catalase, or addition of a complex III inhibitor. Thus, the strategy selected by the differentiation process to allow monocytes to cope with peroxynitrite appears to involve some specific mechanism preventing the mitochondrial formation of H(2)O(2).Thioacetamide (400 mg/kg body weight, i.p.) was administered to rats. After 12 hr the activity of plasma glutamate-oxaloacetate transaminase (GOT) and glutamate-pyruvate transaminase (GPT) was significantly higher than that of the control group, and after 24 hr plasma GOT and GPT activities strongly increased. These results indicated that the necrotic process was initiated at about 12 hr and developed thereafter. By co-administration of dimethyl sulphoxide (DMSO, 18 and 1 hr before, and 8 hr after administration of thioacetamide: each time, 2.5 mL/kg body weight, p.o.), plasma GOT and GPT were significantly decreased and were even comparable to the control group, showing that DMSO totally prevented the necrotic action of thioacetamide. After 12 and 24 hr of thioacetamide administration, the hepatic level of vitamin C, the most sensitive chemical indicator of oxidative stress, decreased significantly, indicating that oxidative stress was significantly enhanced 12 hr after thioacetamide intoxication and thereafter. DMSO totally restored the liver vitamin C level, demonstrating that DMSO effectively ameliorated the oxidative stress caused by thioacetamide, resulting in the prevention of necrosis of the liver. Phosphorylated c-Jun NH(2)-terminal kinase (JNK) significantly increased transiently 12 hr after treatment with thioacetamide. These results indicated that oxidative stress and the activation of JNK took place almost simultaneously. Phosphorylated extracellular signal-related kinase (ERK) 2 was significantly increased 6-12 hr after thioacetamide injection. Phosphorylated p38 MAPK (mitogen activated protein kinase) was significantly decreased 24 hr after administration of thioacetamide. DMSO treatment inhibited the change of these MAPKs by thioacetamide, corresponding with the prevention of the liver necrosis as well as the attenuation of oxidative stress.Evidence is accumulating that irradiated cells produce some signals which interact with non-exposed cells in the same population via a bystander effect. Here, /research/ examined whether DMSO is effective in suppressing radiation induced bystander effects in CHO and repair deficient xrs5 cells. When 1 Gy-irradiated CHO cells were treated with 0.5% DMSO for 1 hr before irradiation, the induction of micronuclei in irradiated cells was suppressed to 80% of that in non-treated irradiated cells. The suppressive effect of DMSO on the formation of bystander signals was examined and the results demonstrated that 0.5% DMSO treatment of irradiated cells completely suppressed the induction of micronuclei by the bystander effect in non-irradiated cells. It is suggested that irradiated cells ceased signal formation for bystander effects by the action of DMSO. To determine the involvement of reactive oxygen species on the formation of bystander signals, /research/ examined oxidative stress levels using the /2,7-dichlorofluorescin/ DCFH staining method in irradiated populations. The results showed that the treatment of irradiated cells with 0.5% DMSO did not suppress oxidative stress levels. These results suggest that the prevention of oxidative stress is independent of the suppressive effect of DMSO on the formation of the bystander signal in irradiated cells. It is suggested that increased ROS in irradiated cells is not a substantial trigger of a bystander signal.Ultrasoft X-rays have been shown to be very efficient in inducing chromosomal aberrations in mammalian cells. The present study was aimed to evaluate the modifying effects of DMSO (a potent scavenger of free radicals) on the frequencies of chromosome aberrations induced by soft X-rays. Confluent held G1 Chinese hamster cells (V79) were irradiated with Carbon K ultrasoft X-rays in the presence and absence of 1M DMSO and frequencies of chromosome aberrations in the first division cells were determined. DMSO reduced the frequencies of exchange types of aberrations (dicentrics and centric rings) by a factor of 2.1-3.5. The results indicate that free radicals induced by ultrasoft X-rays contribute to a great extent to the induction of chromosome aberrations. The possible implications of these results in interpreting the mechanisms involved in the high efficiency of ultrasoft X-rays in the induction of chromosome aberrations are discussed.For more Interactions (Complete) data for DIMETHYL SULFOXIDE (33 total), please visit the HSDB record page. |
| 生態毒性値 | LC50Species: Pimephales promelas (Fathead minnow)Conditions: staticConcentration: 34 g/L for 96 hrSpecies: Salvelinus fontinalis (Brook trout)Concentration: 54 g/L or 24 hr (95% CI: 50.9-58.3 g/L)Species: Salvenilus namaycush (Lake trout)Concentration: 47.8 g/L for 24 hr (95% CI: 42.3-54.0 g/L)Species: Oncorhynchus mykiss (Rainbow trout)Concentration: 53.0 g/L for 24 hr (95%CI: 48.6-57.8 g/L)For more Ecotoxicity Values (Complete) data for DIMETHYL SULFOXIDE (21 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that dimethyl sulfoxide is expected to have very high mobility in soil(SRC). Volatilization of dimethyl sulfoxide from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.03X10-8 atm-cu m/mole(3). Dimethyl sulfoxide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure 0.60 mm Hg(4). The available biodegradation screening tests have conflicting results(5), but based on available data and weight-of-evidence approach, dimethyl sulfoxide is expected to be inherently biodegradable(6). For example, a 3.1% of theoretical BOD using activated sludge in a 2-week Japanese MITI test suggests that dimethyl sulfoxide is not readily biodegradable(7) while 90-99% biodegradation in other screening tests suggest that it is readily biodegradable(5,6).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2(SRC), determined from a structure estimation method(2), indicates that dimethyl sulfoxide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 1.03X10-8 atm-cu m/mole(4). According to a classification scheme(5), BCF values of <4 measured in fish (Cyprinus carpio)(6) suggest the potential for bioconcentration in aquatic organisms is low. Dimethyl sulfoxide is stable to hydrolysis in water(7). The available biodegradation screening tests have conflicting results(8), but based on available data and weight-of-evidence approach, dimethyl sulfoxide is expected to be inherently biodegradable(7). For example, a 3.1% of theoretical BOD using activated sludge in a 2-week Japanese MITI test suggests that dimethyl sulfoxide is not readily biodegradable(6) while 90-99% biodegradation in other screening tests suggest that it is readily biodegradable(7,8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dimethyl sulfoxide, which has a vapor pressure of 0.60 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the atmosphere. Vapor-phase dimethyl sulfoxide 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 4.3 hours(SRC), calculated from its rate constant of 9.0X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase dimethyl sulfoxide is also degraded in the atmosphere by reaction with nitrate radicals which occur predominantly in night-time air(SRC)the half-life for this reaction in air is estimated to be 1.4 hours(SRC), calculated from its rate constant of 5.0X10-13 cu cm/molecule-sec at 25 °C(3). Dimethyl sulfoxide does not absorb light at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). Dimethyl sulfoxide has been detected in rainwater(5) indicating that it may be removed from the air by wet deposition(SRC). |
| 食品調査値 | Dimethyl sulfoxide occurs widely at levels of 3 ppm or less(1). It has been isolated from spearmint oil, corn, barley, malt, alfalfa, beets, cabbage, cucumbers, oats, onion, Swiss chard, tomatoes, raspberries, coffee, and tea(1). |
| 有害作用 | Neurotoxin - Acute solvent syndrome |
| 暴露経路 | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.Topicalparenteral(intravesical). Readily and rapidly absorbed following administration by all routes and distributed throughout the body. |
| 毒性の概要 | IDENTIFICATION AND USE: Dimethyl sulfoxide (DMSO) is a colorless, very hygroscopic, liquid. It is a molecule with a long history in pharmaceutics and is now well established as a penetration enhancer in topical pharmaceutical formulations. It is currently prescribed as medication for this purpose in diclofenac sodium topical solution (approved in the United States to treat signs and symptoms of osteoarthritis) and idoxuridine topical solution (approved in Europe for the treatment of herpes zoster). DMSO is used as a medication for symptomatic relief of interstitial cystitis. DMSO is not a nutritional supplement, it is metabolized to methylsulfonylmethane (MSM), which is available as a nutritional supplement. DMSO is used in the cryopreservation of cell populations including stem cells, embryos, and various cell cultures. It is also used as an Industrial solvent and as antifreeze or hydraulic fluid when mixed with water. HUMAN EXPOSURE AND TOXICITY: Dermal exposure to DMSO causes skin reactions, erythema and pruritis, which appear immediately after contact with the undiluted substance70% solutions are usually tolerated without symptoms. In very sensitive individuals, however, reactions have been seen after contact with 10% solutions. In humans, topical and intradermal application of DMSO produced garlic breath, mast cell degranulation, an increase in polymorphonuclear leukocytes and perivascular eosinophils, itching, and histamine mediated and non-histamine dependent whealing and erythematous flare. Two drops of >50% DMSO in the eye caused a temporary burning sensation and vasodilatationconcentrations of <50% exhibited no effects. A case of sulhemoglobinemia after dermal exposure to DMSO has been described. ANIMAL STUDIES: To study the effects of acute DMSO exposure unshaven rats were immersed in a DMSO solution. There was no immediate response, but within 24 hours 13/14 rats dipped into 100% DMSO were dead. Single i.v. injections of undiluted DMSO were administered to groups of 5 male and 5 female rats. Dose levels were 2.5, 5.0, and 10 g/kg. Each dose was administered over a 1-minute interval. Animals were observed for 14 days following DMSO administration and with one exception, deaths occurred within the first 24 hours. Death was preceded by tremors, myasthenia, dyspnea, and occasionally, convulsions. Non-lethal doses of DMSO produced decreased motoractivity and myasthenia. A total of 32 male rats were exposed to 200 mg DMSO per cubic meter of air for 7 hr/day, 5 days a week, for 6 weeks for 30 exposures. There were no outward toxic signs noted in any of the exposed animals throughout the experimental period of 6 weeks. A garlic-like odor, characteristic of DMSO exposure, was detected in the breath of each of the rats after the first day of exposure. Pharmaceutical-grade DMSO was administered as a 90% solution to 4 groups of rhesus monkeys by gastric intubation, 7 days a week for up to 87 weeks. Dosages administered were equivalent to 990, 2970, and 8910 mg/kg/day. The principal physical signs seen in the animals given DMSO orally included sporadic excess salivation and emesis. Anorexia only occurred at high oral doses. No DMSO-related changes were found in the treated monkeys during physical examinations. No significant lesions attributable to DMSO were found upon gross examination at necropsy. No histologic changes were visible in the lenses of treated animals. In developmental studies groups of 5 -6 pregnant golden hamsters were injected with dilutions of DMSO ranging from 50 to 5500 mg/kg iv or 5500 and 8250 mg/kg ip on the eighth day of gestation. Examination of the embryos 3 days later revealed that no embryocidal or teratogenic effects were noted until levels of 2500 mg/kg were reached. At higher levels, malformations, including exencephaly, rib fusions, microphthalmia, limb abnormalities and cleft lip were found. There was no appreciable effect of DMSO on maternal weight gain or health. DMSO was tested in Chinese hamster ovary cells to a maximum concentration of 5000 ug/mL with and without metabolic activation. DMSO did not induce cell toxicity or cell cycle delay, and did not induce an increase in the incidence of SCEs. Intraabdominal injection of DMSO did not induce sex-linked recessive lethals and did not raise the frequency of sex chromosome loss above the spontaneous level in Drosophila melanogaster. DMSO was tested in five S. typhimurium tester strains (TA 98, 100, 1535, 1537, 1538). DMSO was negative, in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: The acute toxicity (g/kg bw) of i.p. DMSO injection to chinook salmon (Oncorhynchus tshawytscha): LD50 = 12.0, sockeye salmon (Oncorhynchus nerka): LD50 = 13.0, coho salmon (Oncorhynchus kisutch): LD50 = 16.0 and rainbow trout (Salmo gardneri): LD50 = 17.0. Fish usually died within 24 hrhowever, a few died between 24 and 48 hours.The mechanism of dimethyl sulfoxide's actions is not well understood. Dimethyl sulfoxide has demonstrated antioxidant activity in certain biological settings. For example, the cardiovascular protective effect of dimethyl sulfoxide in copper-deficient rats is thought to occur by an antioxidant mechanism. It is also thought that dimethyl sulfoxide's possible anti-inflammatory activity is due to antioxidant action. |
| 生態毒性抜粋 | /AQUATIC SPECIES/ The acute toxicity (g DMSO/kg body weight) of DMSO to Chinook salmon (Oncorhynchus tshawytscha): LD50 = 12.0, Sockeye salmon (Oncorhynchus nerka): LD50 = 13.0, Coho salmon (Oncorhynchus kisutch): LD50 = 16.0 and Rainbow trout (/Oncorhynchus mykiss/) LD50 = 17.0 was determined by intraperitoneal injections of aqueous solutions of DMSO. Fish usually died within 24 hrhowever, a few died between 24 and 48 hours. Symptoms of toxicity were intermittent spasms and disorientation of swimming shortly before expiring. In the preliminary chronic study, moderate hematologic changes were observed in fish receiving daily injections of 9.0 - 31 g/kg bw (30-100% DMSO) and consisted in slight pyknosis of red blood cell nuclei and moderate degeneration of white blood cells. Average death rates for this group was: 31 g/kg (100%), 4 hr12 g/kg (50%), 33 hr10 g/kg (40%), 90 hr and 9.0 g/kg (30%), 130 hr. No mortality was observed in fish injected with 0.9 g/kg. Histologic alterations noted in fish injected with 31 g/kg were confined to liver, kidney, spleen and pancreas./AQUATIC SPECIES/ Addition of 5% solution of DMSO to cultures caused changes in motor behavior of the cells during the first hr of incubation, enhanced cell adhesions to substratum and fusions between pseudopodia of the same ameba./AQUATIC SPECIES/ No mortality was observed when DMSO (0.01% to 20% v/w) was fed as a dietary ingredient. Fish ingesting DMSO displayed a dose-dependent decrease in diet consumption and body weight gain. Hematologic differences were noted in fish receiving 15 and 18% DMSO in their diets. Histopathological examinations were conducted on fish fed 6, 12, and 18% DMSO. Lesions observed in the 12% group were confined to gill lamellae and consisted of moderate edema and moderate to severe epithelial cell hypertrophy. Similar, more pronounced changes were observed fish receiving 18% DMSO./OTHER TOXICITY INFORMATION/ Newts were collected during the summer and spring, acclimated for 10 days at 10 °C, weighed, treated with DMSO and maintained in an unfed state which simulated winter conditions. Intraperitoneal injections of 15 g DMSO/kg or immersion in 2% DMSO were determined to be lethal threshold doses for newts. Death was rapid. In addition to a transient increase in the body weight of the DMSO-treated animals, other changes observed /were/: a reduction in respiration to 70% that of the controlsan increase in the weights of spleen (by day 1, the average spleen weight was over twice that of the controls), liver (33% increase after 24 hr), and abdominal fat (150% increase after 20 days). Lethality was attributed primarily to irreversible changes in the permeability of the skin, causing a water imbalance, hyperhydration and death.The reduced respiratory rate increased the mortality rate. |
| Plant Concentrations | Dimethyl sulfoxide occurrence in plants(1).[Table#220] |
| Signs and Symptoms | Garlic odour. Headache. Nausea.Redness.Garlic breath. Nausea. Vomiting. Drowsiness. Diarrhoea.Taking DMSO internally is reported to cause a fish- or oyster-like taste or odor in the mouth, likely due to the sulfoxide metabolites of DMSO. [Wikipedia] |
| Acute Toxicity Link | Chemical: DIMETHYLSULFOXIDE |
| 大気基準 | This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Dimethyl sulfoxide is produced, as an intermediate or a final product, by process units covered under this subpart. |
| F | 3 |
| 水環境危害等級（WGK） | 1 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | PV6210000 |
| 輸送番号（UN） | NA 1993 / PGIII |
| 毒性 | LD50 orally in rats: 17.9 ml/kg (Bartsch) |
| 税関コード | 29309070 |
| 危険文句（R） | 36/37/38 |
| 化審法 | (2)-1553 |
| 消防法 | 危険物第4類第三石油類(水溶性) |
| 危険表示 | Xi |
| 安全措置（S） | 24/25-37/39-26-36-23 |
| 危険等級 | CBL |
| 自然発火温度 | 215 °C |
| 環境リスク評価 | ジメチルスルホキシド(67-68-5) |
| 貯蔵分類 | 10 - Combustible liquids |
| 有害物質データ | 67-68-5(Hazardous Substances Data) |
用途
解説
C2H6OS(78.14)．(CH3)2S=O．ジメチルスルホキシドは，略称DMSO．ジメチルスルフィドを酸化すると得られる．無色，無臭，吸湿性の液体．融点18.9 ℃，沸点189 ℃(分解)．d420"1.1014．nD20"1.4795．水，エタノール，アセトン，エーテル，ベンゼン，クロロホルムに溶解する．脂肪族炭化水素は溶かさない．石油中の芳香族留分の抽出溶剤，およびアセチレン，二酸化硫黄，二酸化窒素などのガス溶剤，また各種樹脂の溶剤として用いられる．還元されてジメチルスルフィドになり，酸化されてジメチルスルホンを与える．各種の弱い酸化反応の酸化剤として有機合成に広く用いられる．ポリアクリロニトリル，ポリエチレンテレフタラートなどの高分子化合物の溶剤として用いられるほか，穏やかな酸化剤としても用いられる. LD50 19700 mg/kg(ラット，経口)．森北出版「化学辞典（第2版）
用途
繊維の紡糸液、医薬品原料
用途
アクリル繊維、医薬、農薬などの合成、染料、顔料用溶剤、剥離.洗浄剤.
用途
分析用溶剤、有機合成溶剤。
説明
First synthesized in 1866 by Alexander Zaytsev in the Russian Empire, dimethyl sulfoxide is an organosulfur compound. This colorless liquid is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.
天然物の起源
Reported found in apple, raspberry, cabbage, cucumber, onion, tomato, peppermint and spearmint oils, milk, pork liver, beer, rum, cocoa, coffee, black tea, oatmeal, soybean, beetroot, parsnip root, watercress, sweet corn, malt, cooked shrimp and oysters
使用
Dimethyl sulfoxide (1-10%) has been shown to accelerate strand renaturation and is believed to give the nucleic acid thermal stability against depurination. As a PCR cosolvent, DMSO may help improve yields, especially in long PCR.
一般的な説明
A clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.
製法・合成法
調製方法
Dimethyl sulfoxide is prepared by air oxidation of dimethyl sulfide in the presence of nitrogen oxides. It can also be obtained as a by product of wood pulp manufacture for the paper and allied industries.
純化方法
This colourless, odourless, very hygroscopic liquid, is synthesised from dimethyl sulfide. The main impurity is water, with a trace of dimethyl sulfone. The Karl-Fischer test is applicable. It is dried with Linde types 4A or 13X molecular sieves, by prolonged contact and passage through a column of the material, then distilled under reduced pressure. Other drying agents include CaH2, CaO, BaO and CaSO4. It can also be fractionally crystallised by partial freezing. More extensive purification is achieved by standing overnight with freshly heated and cooled chromatographic grade alumina. It is then refluxed for 4hours over CaO, dried over CaH2, and fractionally distilled at low pressure. For efficiency of desiccants in drying dimethyl sulfoxide see Burfield and Smithers [J Org Chem 43 3966 1978, Sato et al. J Chem Soc, Dalton Trans 1949 1986]. [Reddy Pure Appl Chem 25 459 1969, Beilstein 1 IV 1277.] Rapid purification: Stand over freshly activated alumina, BaO or CaSO4 overnight. Filter and distil it over CaH2 under reduced pressure (~ 12 mm Hg). Store it over 4A molecular sieves.