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1-(1-ナフチル)-2-チオ尿素
1-(1-ナフチル)-2-チオ尿素 · クリシド · ラットラック · バンツ · 1-(1-ナフチル)チオ尿素 · アンツラット · N-(1-ナフチル)チオ尿素 · 1-ナフチルチオ尿素
識別子と物理属性
| CAS No. | 30553-04-9 |
|---|---|
| 分子式 | C11H10N2S |
| 平均分子量 | 202.28 g/mol |
| 単同位体質量 | 202.05646932 g/mol |
| SMILES | NC(=S)Nc1cccc2ccccc12 |
| InChIKey | PIVQQUNOTICCSA-UHFFFAOYSA-N |
| PubChem CID | 736366 |
| ChEMBL | CHEMBL3182781 |
| ChEBI | CHEBI:82256 |
| EC No. | 201-706-3 |
| DTXSID | DTXSID8020919 |
| 現地名 | 1-(1-ナフチル)-2-チオ尿素 |
化学・物理的性質
| XLogP | 1.7 |
|---|---|
| 極性表面積 | 70.1 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 1 |
| 重原子数 | 14 |
| 形式電荷 | 0 |
| 複雑度 | 217 |
| 農薬 | Pesticides -> Rodenticides |
| LogP（分配係数） | log Kow = 1.651.66 (calculated) |
| 臭い | Odorless苦味 |
| 味 | Bitter taste |
| 密度 | Specific Gravity (water= 1): Greater than 1>1 g/cm³1.333 |
| Color/Form | Prisms from alcoholColorless ... solidWhite, crystalline or gray powder |
| 溶解度 | 0.06 % (NIOSH, 2024)In water, 600 mg/L at 25 °CSolubility in acetone = 2.43 g/100 mLin triethylene glycol = 8.6 g/100 mLfairly soluble in hot alcoholSlightly soluble in ethanol, ethyl ether, acetoneVery slightly soluble in most organic solventsSolubility in water: noneアセトンおよびトリエチレングリコール中、それぞれ 4.3 および 86 g/L (Windholz et al., 1983)20°C で 600 mg/L (Windholz et al., 1983 から引用) |
| 引火点 | May burn but will not ignite readily (EPA, 1998) |
| 沸点 | Decomposes (NIOSH, 2024)400 °C @760 [mm Hg]377.6±25.0 °C(Predicted) |
| Decomposition | Hazardous decomposition products include: sulfur dioxide, oxides of nitrogen, and carbon monoxide.When heated to decomp ...it emits toxic fumes of /nitrogen oxides and sulfur oxides./ |
| 融点 | 388 °F (EPA, 1998)198 °C193 °C |
| 蒸気密度 | 6.99 (EPA, 1998) - Heavier than airwill sink (Relative to Air) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | Poison room |
| pKa（酸解離定数） | 13.12±0.70(Predicted) |
| 外観・状態 | 結晶または結晶性粉末 |
| 色 | グレーがかったベージュブラウン |
| Merck | 14,722 |
| BRN | 778118 |
| ヘンリー定数 | 1.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 主な用途 | 農業環境 |
| InChI | 1S/C11H10N2S/c12-11(14)13-10-7-3-5-8-4-1-2-6-9(8)10/h1-7H,(H3,12,13,14) |
| InChIKey | PIVQQUNOTICCSA-UHFFFAOYSA-N |
| SMILES | NC(=S)Nc1cccc2ccccc12 |
| CAS データベース | 86-88-4(CAS DataBase Reference) |
| EPAの化学物質情報 | .alpha.-Naphthylthiourea (86-88-4) |
化学的特性
greyish to beige-brown crystals or cryst. powder
安全性と法規制
| GHS 分類 | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral] |
|---|---|
| 規制情報 | The 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.) |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Emits sulfur dioxide, oxides of nitrogen, and carbon monoxide fumes upon decomposition. It reacts with silver nitrate and strong oxidizers. Avoid decomposing heat. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily.Combustible under specific conditions. Gives off irritating or toxic fumes (or gases) in a fire. |
| 火災の可能性 | /To fight fire use:/Powder, water spray, foam, carbon dioxide. |
| 健康有害性 | Moderately toxic: probable oral lethal dose (human) 0.5-5 gm/kg, or between 1 ounce and 1 pint (or l lb.) for 150 lb. person. Chronic sublethal exposure may cause antithyroid activity. Can produce hyperglycemia of three times normal in three hours. People with chronic respiratory disease or liver disease may be especially at risk. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| 有害性の概要 | The lethal oral dose in humans is about 4 g/kgTLV based on thyroid effects and nauseaIn high-dose feeding and intraperitoneal injection studies, animals develop liver injury, pleural and pericardial effusions, and pulmonary edema. [ACGIH] |
| 輸送番号・ガイド（DOT） | 1651 153 |
| 反応性グループ | Amides and Imides |
| EC 分類 | Symbol: T+R: 28-40S: (1/2)-25-36/37-45 |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | Harris WFCurr Vet Ther 6: 117-9 (1977). A review with 2 references of the mechanism of ANTU toxicity, poisoning, & its treatment.Boyd MRCRC Crit Rev Toxicol 7 (2): 103-76 (1980). An extensive review of the in vivo biotransformation is presented. |
| RCRA 要件 | P072As stipulated in 40 CFR 261.33, when alpha-naphthylthiourea, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)). |
| 消火 | Stay upwind, and out of low areas. Wear self-contained breathing apparatus and full protective clothing.Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Give a slurry of activated charcoal in water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention . |
| 漏出応急措置 | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| 応急処置 | Signs and Symptoms of ANTU Exposure: Acute exposure to ANTU may result in skin irritation, vomiting, difficult breathing, noisy breathing, pulmonary edema or effusion, low body temperature, and seizures. Antithyroid activity and hyperglycemia may be observed after chronic sublethal exposure.Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:General First Aid:(General first aid procedures) |
| 安全保管 | Separated from strong oxidants, silver nitrate and food and feedstuffs. |
| Firefighting Hazards | Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx), sulphur oxides. |
| 暴露管理・個人防護 | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| 消火手順 | If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty). Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Naphthylthiourea/Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary. |
| 保管条件 | Separated from strong oxidants, silver nitrate, food and feedstuffs.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. |
| 清掃方法 | Ventilate area of spill. For small quantities, sweep onto paper or other suitable material, place in appropriate container and burn in safe place (such as fume hood). Large quantities may be reclaimed ... If not practical, dissolve in flammable solvent ... and atomize in ... combustion chamber ...Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| 非火災時の漏出対応 | Avoid inhalation and skin contact. Do not touch spilled material, stay upwind, keep out of low areas, deny entry. (EPA, 1998)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 処分方法 | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P072, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids.Incinerate in a furnace equipped with an alkaline scrubber. Recommendable methods: Incineration & landfill. ... (Peer-review conclusions of an IRPTC expert consultation (May 1985))Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal. |
| 相互作用 | Acute lung injury is an inflammatory syndrome that increases the permeability of the blood-gas barrier, resulting in high morbidity and mortality. Despite intensive research, treatment options remain limited. /This study/ investigated the protective efficacy of tezosentan, a novel, dual endothelin receptor antagonist, in an experimental model of alpha-naphthylthiourea (ANTU)-induced acute lung injury in rats. ANTU was intraperitoneally (i.p.) injected into rats at a dose of 10 mg/kg. Tezosentan was injected 30 minutes before ANTU was subcutaneously (s.c.) injected at doses of 2, 10, or 30 mg/kg, 60 minutes before ANTU was injected at doses of 2, 10, or 30 mg/kg (i.p.), and 90 minutes before ANTU at a dose of 10 mg/kg (i.p.). Four hours later, the lung weight/body weight (LW/BW) ratio and pleural effusion (PE) were measured. When injected 30 minutes before ANTU at doses of 2, 10, or 30 mg/kg (s.c.), tezosentan had no effect on lung pathology. When injected 60 minutes before ANTU at doses of 2, 10, or 30 mg/kg (i.p.) or 90 minutes before ANTU (10 mg/kg, i.p.), tezosentan significantly decreased the PE/BW ratio and had a prophylactic effect on PE formation at all doses. Therefore, tezosentan may attenuate lung injury. Furthermore, its acute and inhibitory effects on fluid accumulation were more effective in the pleural cavity than in the interstitial compartment in this experimental model.This study was designed to investigate the possible participation of morphine in pulmonary edema induced by alpha-naphthylthiourea (ANTU), which is a well-known noxious chemical agent in the lung. Injection of ANTU (15 mg/kg i.p.) produced pulmonary edema as indicated by an increase in lung weight/body weight ratio and pleural effusion reaching a maximum within 4 hr in rat. Administration of morphine prior to ANTU significantly inhibited to pulmonary edema with a dose-dependent manner. The protective effect of morphine is prevented by peripheral opioid receptor antagonist, naloxone methiodide. ANTU-treated rats were shown positive by inducible nitric oxide synthase immunohistochemical staining. There was no staining in the control group. On the other hand, the degree of staining was markedly reduced in tissue sections by morphine. These results suggest that previous administration of subcutaneous morphine has preventive effect on ANTU-induced pulmonary inflammatory reaction and its effect mediated via peripheral opioid receptors. Application of naloxone with ANTU has no effect on the lung parameters indicating that endogenous opioids do not modulate ANTU-induced damage.Iodine or iodide given to animals 6 hours prior to ANTU affords significant protection, but neither is effective after exposure.... Pretreatment of mice with 4-ipomeanol produced tolerance to alpha-naphthylthiourea. ... /Dose not specified/.For more Interactions (Complete) data for ALPHA-NAPHTHYLTHIOUREA (11 total), please visit the HSDB record page. |
| 標的器官 | respiratory system, blood, liver |
| 生態毒性値 | LC50Species: Anas platyrhychos (Mallard duck) 10 day olddietary 3,400 ppm for 5 days (95% confidence interval: 2378-4362 ppm)Species: Colinus virginianus (Northern bobwhite) 10 day olddietary 8,200 ppm for 5 days (95% confidence interal: 5,563-12,087 ppm) |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3600(SRC), determined from a structure estimation method(2), indicates that alpha-naphthylthiourea is expected to have slight mobility in soil(SRC). The pKa of alpha-naphthylthiourea is estimated as 9.47(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of neutral alpha-naphthylthiourea from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). The ionic form of alpha-naphthylthiourea is not expected to volatilize because ions do not volatilize. alpha-Naphthylthiourea is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.1X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2014).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3600(SRC), determined from a structure estimation method(2), indicates that alpha-naphthylthiourea is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 9.47(3) indicates alpha-naphthylthiourea will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization of the ionic form from water surfaces is not expected to be an important fate process(SRC). Volatilization of the neutral form from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 8.5X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). The hydrolysis half-life for alpha-naphthylthiourea is 361 days based on a measured hydrolysis rate constant of 2.2X10-8 L/mol sec at pH 7 and 25 °C(6). According to a classification scheme(7), an estimated BCF of 5.7(SRC), from a log Kow of 1.65(8) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2014).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), alpha-naphthylthiourea, which has an estimated vapor pressure of 1.1X10-6 Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase alpha-naphthylthiourea 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 1.6 hours(SRC), calculated from its rate constant of 2.2X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase alpha-naphthylthiourea may be removed from the air by wet and dry deposition(SRC). alpha-Naphthylthiourea contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| 食品調査値 | alpha-Naphthylthiourea was not detected (detection limit not reported) in wheat, barley or oat grain samples from Ciudad Real, Spain(1). |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.inhalation, ingestion |
| 毒性の概要 | IDENTIFICATION AND USE: Alpha-Naphthyl thiourea (ANTU) is a white, crystalline, or gray odorless powder with a bitter taste. It was first used as a rodenticide for the control of adult Norway rats. It was widely used in the 1940s but has subsequently been replaced by other compounds in most countries including the U.S. It is not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: ANTU is well absorbed by skin contact and inhalation. Oral ingestion may result in vomiting, shortness of breath, bluish discoloration of the skin, pulmonary edema or liver injury. Repeat exposures can injure the thyroid and adrenals, producing hypothyroidism. ANIMAL STUDIES: Oral feeding of ANTU to rats at 10 mg/kg body weight increased the blood glucose levels by 100% after 22 hours. Acute exposure also caused elevated plasma activities of aspartate and alanine aminotransferases and increased the activity of the lactate dehydrogenase 5 (LD5) isoenzyme, suggesting that the liver is one of the targets in poisoning in ANTU-treated rats. Toxic symptoms observed in laboratory animals given repeated doses of alpha-naphthyl thiourea include impaired weight gain and deformities of the legs and feetinhibition of hair growth and defective hair pigmentationthyroid hyperplasia and hypercholesterolemiaand fatty degeneration of the liver and bile-duct proliferation. Other effects that have been reported are inhibition of pulmonary aniline hydroxylase activity, increased pulmonary aminopyrine demethylase activity and inhibition of Na+/K+ ATPases in erythrocyte membranes and kidney microsomes. Microsomes from rat liver and lung release atomic sulfur from alpha-naphthyl thiourea. Pulmonary toxicity may result, at least in part, from binding of atomic sulfur to tissue macromolecules in susceptable species. ANTU is mutagenic when metabolized by liver microsomal fractions from rats treated with either Aroclor 1254 or phenobarbital. It also transforms hamster embryo cells in an in vitro carcinogenesis bioassay. |
| Signs and Symptoms | Cough. Laboured breathing. Shortness of breath.MAY BE ABSORBED!Abdominal pain. Vomiting. Laboured breathing.After ingestion of large doses: vomiting, dyspnea (breathing difficulty), cyanosis, coarse pulmonary ralesliver damage |
| Medical Surveillance | Employees should be screened for history of certain medical conditions such as individuals with chronic respiratory disease or liver disease, which might place the employee at an increased risk from ANTU exposure. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of alpha-naphthylthiourea can be estimated to be 3600(SRC). According to a classification scheme(2), this estimated Koc value suggests that alpha-naphthylthiourea is expected to have slight mobility in soil. The pKa of alpha-naphthylthiourea is estimated as 9.47(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). |
| Natural Pollution Sources | alpha-Naphthylthiourea is not known to occur as a natural product. |
| CERCLA 報告数量 | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. ANTU is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 micronsor is handled in solution or in molten formor meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . |
| 職業暴露区分（OEB） | C |
| 職業暴露限界（OEL） | TWA: 0.3 mg/m3 |
| 水環境危害等級（WGK） | 2 |
| 生命健康即時危険濃度 | 100 mg/m3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | YT9275000 |
| 輸送番号（UN） | UN 1651 |
| 毒性 | Acute oral LD50 for Norwegian rats 6–8 mg/kg (Hartley and Kidd, 1987). |
| 税関コード | 29309090 |
| 危険文句（R） | 28-40 |
| 安衛法 | 57,57-2 |
| 危険表示 | T+ |
| 安全措置（S） | 28-36/37-45-25-23 |
| 危険等級 | 6.1Acute Tox. 2 OralCarc. 2 |
| 包装等級 | II |
| 貯蔵分類 | 6.1A - Combustible, acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 86-88-4(Hazardous Substances Data) |
用途
用途
農薬(殺ソ剤)
説明
a-Naphthylthiourea (ANTU; also called DIRAX) is toxic by inhalation, ingestion, or skin contact. Due to its very narrow spectrum of activity, production was discontinued a long time ago. Exposure to ANTU causes pulmonary edema; therefore, it is often used as an experimental pneumotoxin. ANTU is a graycolored, prism-shaped, odorless powder with a bitter taste. It has a molecular weight of 202.28 and melting point of 200 ℃ and does not ignite readily. However, on interaction with potential oxidizing agents, it may cause fire and explosions, which can lead to hazardous decomposition products such as sulfur dioxide, nitrogen dioxide, and carbon monoxide. The structure of ANTU contains the naphthalene chromophore, which absorbs UV light at ～311 nm. This suggests that ANTU can undergo photolysis.
使用
Rodenticide. Specific control for the adult Norway rat; less toxic to other rat species.
一般的な説明
White crystal or powder; technical product is gray powder. Has no odor but a bitter taste. Used primarily as a rodenticide for control of adult Norway rats. Not produced commercially in the U.S.
製法・合成法
純化方法
Crystallise ANTU from EtOH. [Beilstein 12 III 2941, 12 IV 3086.]