2180-92-9

• 常用中文名：丁吡卡因
• 常用英文名：Bupivacaine
• CAS号：2180-92-9
• 分子式：C₁₈H₂₈N₂O
• 分子量：288.428
• 相关类别： 原料药 Anesthetic Agents Local anesthetics
• 发布时间：2018-03-31 08:00:00
• 更新时间：2024-01-05 16:43:40
• 【用途一】
  该品是一种安全有效的局部麻醉药，日本、英国、美国、德国均有生产。丁吡卡因盐酸对小白鼠（皮下给药）LD50为82±6mg/kg。家免持续静脉给药所致痉挛量（CD50）为0.18±0.02mg/kg/min。

名称

• 中文名: 丁吡卡因
• 英文名: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
• 中文别名: 布比卡因
• 英文别名: 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2S)-; (2S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; Bupivacaine; L-(-)-Bupivacaine; (-)-Bupivacaine; Levobupivacaine; MFCD00243007; EINECS 218-553-3; (S)-(-)-Bupivacaine; (S)-Bupivacaine; (2S)-1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; (RS)-bupivacaine

物化性质

• 密度: 1.0±0.1 g/cm3
• 沸点: 423.4±45.0 °C at 760 mmHg
• 分子式: C₁₈H₂₈N₂O
• 分子量: 288.428
• 闪点: 209.9±28.7 °C
• 精确质量: 288.220154
• PSA: 32.34000
• LogP: 3.64
• 蒸汽压: 0.0±1.0 mmHg at 25°C
• 折射率: 1.547
• 储存条件:

  库房通风低温干燥; 与食品原料分开存放

• 分子结构:

  1、 摩尔折射率：88.62

  2、 摩尔体积（cm³/mol）：279.2

  3、 等张比容（90.2K）：709.0

  4、 表面张力（dyne/cm）：41.5

  5、 极化率（10-24cm3）：35.13

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:2

  4.可旋转化学键数量:5

  5.互变异构体数量:3

  6.拓扑分子极性表面积32.3

  7.重原子数量:21

  8.表面电荷:0

  9.复杂度:321

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:1

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：白色结晶性粉末

  2.熔点（ºC）：255～256

  3.溶解性：易溶于水、乙醇、难溶于氯仿，几乎不溶于乙酸乙酯。无臭、味苦。

MSDS

Section 1. Chemical Product and Company Identification Bupivacaine Base Common Name/ Trade Name Bupivacaine Base Section 4. First Aid Measures Eye ContactCheck for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Cold water may be used. Get medical attention if irritation occurs. Skin ContactIn case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Cover the irritated skin with an emollient. Cold water may be used.Wash clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately. Serious Skin ContactNot available. InhalationIf inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical attention immediately. Serious InhalationEvacuate the victim to a safe area as soon as possible. Loosen tight clothing such as a collar, tie, belt or waistband. If breathing is difficult, administer oxygen. If the victim is not breathing, perform mouth-to-mouth resuscitation. WARNING: It may be hazardous to the person providing aid to give mouth-to-mouth resuscitation when the inhaled material is toxic, infectious or corrosive. Seek immediate medical attention. IngestionIf swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Loosen tight clothing such as a collar, tie, belt or waistband. Get medical attention immediately. Serious IngestionNot available. Section 5. Fire and Explosion Data Flammability of the Product May be combustible at high temperature. Auto-Ignition Temperature Not available. Not available. Flash Points Not available. Flammable Limits Products of CombustionThese products are carbon oxides (CO, CO2), nitrogen oxides (NO, NO2...). Fire Hazards in Presence of Slightly flammable to flammable in presence of heat. Various Substances Explosion Hazards in Presence Risks of explosion of the product in presence of mechanical impact: Not available. Risks of explosion of the product in presence of static discharge: Not available. of Various Substances Fire Fighting MediaSMALL FIRE: Use DRY chemical powder. and InstructionsLARGE FIRE: Use water spray, fog or foam. Do not use water jet. As with most organic solids, fire is possible at elevated temperatures Material in powder form, capable of creating Special Remarks on Fire Hazardsa dust explosion. Special Remarks on Explosion Fine dust dispersed in air in sufficient concentrations, and in the presence of an ignition source is a potential dust Hazardsexplosion hazard. Section 6. Accidental Release Measures Small SpillUse appropriate tools to put the spilled solid in a convenient waste disposal container. Large SpillPoisonous solid. Stop leak if without risk. Do not get water inside container. Do not touch spilled material. Use water spray to reduce vapors. Prevent entry into sewers, basements or confined areas; dike if needed. Eliminate all ignition Bupivacaine Base Section 7. Handling and Storage PrecautionsKeep away from heat. Keep away from sources of ignition. Ground all equipment containing material. Do not ingest. Do not breathe dust. Wear suitable protective clothing. If ingested, seek medical advice immediately and show the container or the label. Keep away from incompatibles such as oxidizing agents. StorageKeep container tightly closed. Keep container in a cool, well-ventilated area. Section 8. Exposure Controls/Personal Protection Engineering ControlsUse process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants below the exposure limit. Personal ProtectionSafety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves. Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used a Large Spillto avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this product. Exposure LimitsNot available. Section 9. Physical and Chemical Properties Physical state and appearance Solid. (Crystalline powder.)OdorOdorless. TasteNot available. Molecular Weight288.43 g/mole ColorWhite. pH (1% soln/water)Not available. Not available. Boiling Point Melting PointNot available. Not available. Critical Temperature Specific GravityNot available. Vapor PressureNot applicable. Vapor DensityNot available. VolatilityNot available. Odor ThresholdNot available. Water/Oil Dist. Coeff.Not available. Ionicity (in Water)Not available. Dispersion PropertiesSee solubility in water, acetone. SolubilityEasily soluble in cold water. Partially soluble in acetone. Section 10. Stability and Reactivity Data StabilityThe product is stable. Not available. Instability Temperature Conditions of InstabilityExcess heat, dust generation Incompatibility with variousReactive with oxidizing agents. substances CorrosivityNot available. Bupivacaine Base Special Remarks onNot available. Reactivity Special Remarks onNot available. Corrosivity PolymerizationWill not occur. Section 11. Toxicological Information Routes of EntryInhalation. Ingestion. Toxicity to AnimalsLD50: Not available. LC50: Not available. Chronic Effects on Humans Not available. Other Toxic Effects on Hazardous in case of ingestion. HumansSlightly hazardous in case of skin contact (irritant), of inhalation. Special Remarks onNot available. Toxicity to Animals Special Remarks on May cause adverse reproductive effects and birth defects (teratogenic)based on animal test data. Chronic Effects on Humans Special Remarks on otherAcute Potential Health Effects: Toxic Effects on HumansSkin: Skin contact may cause skin irritation. Injection under the skin causes local anesthesia. Eyes: May cause eye irritation. Inhalation: Inhalation of dust may cause respiratory tract irritation. Ingestion: May cause gastrointestinal tract irritation, nausea, vomiting, central nervous system depression or stimulation, dizziness, somnolence, headache, weakness, itching, skin rash, hives, shivering, back pain, bluish lips and fingernails, numbness, cardiovascular depression, irregular heartbeat, bradyarrhythmiahypotension, breathing problems or inability to breath, unconsciousness, and convulsions. May also affect liver, blood (changes in serum composition) Note: Possible allergic reaction to material if inhaled, ingested or in contact with skin. Medical Conditions Aggravated by Exposure: Hypersensitivity to material; heart problems; liver function impairment; sensitivity to amide-type local anesthetics. Section 12. Ecological Information EcotoxicityNot available. BOD5 and CODNot available. Products of BiodegradationPossibly hazardous short term degradation products are not likely. However, long term degradation products may arise. Toxicity of the ProductsThe products of degradation are less toxic than the product itself. of Biodegradation Special Remarks on theNot available. Products of Biodegradation Section 13. Disposal Considerations Waste DisposalWaste must be disposed of in accordance with federal, state and local environmental control regulations. Bupivacaine Base Section 14. Transport Information DOT ClassificationCLASS 6.1: Poisonous material. Identification: Alkaloid, solid, n.o.s (bupivacaine) UNNA: 1544 PG: III Not available. Special Provisions for Transport DOT (Pictograms) HARMFUL STOW AWAY FROM FOODSTUFFS 6 Section 15. Other Regulatory Information and Pictograms No products were found. Federal and State Regulations CaliforniaCalifornia prop. 65: This product contains the following ingredients for which the State of California has found to cause cancer which would require a warning under the statute: No products were found. Proposition 65 Warnings California prop. 65: This product contains the following ingredients for which the State of California has found to cause birth defects which would require a warning under the statute: No products were found. Other RegulationsOSHA: Hazardous by definition of Hazard Communication Standard (29 CFR 1910.1200). EINECS: This product is on the European Inventory of Existing Commercial Chemical Substances (EINECS No. 218-553-3). Canada: Not listed on Canadian Domestic Substance List (DSL) or Canadian Non-Domestic Substances List (NDSL) China: Not isted on National Inventory. Japan: Listed on National Inventory (ENCS). Korea: Not listed on National Inventory (KECI). Philippines: Not listed on National Inventory (PICCS). Australia: Listed on AICS. WHMIS (Canada) CLASS D-1B: Material causing immediate and serious toxic effects (TOXIC). Other Classifications DSCL (EEC)R25- Toxic if swallowed.S45- In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). Health Hazard HMIS (U.S.A.)2 National Fire Protection 1 Flammability 1 Association (U.S.A.) Fire Hazard 2 0 Reactivity Health Reactivity 0 Specific hazard Personal Protection E WHMIS (Canada) (Pictograms) DSCL (Europe) (Pictograms) Bupivacaine Base TDG (Canada) (Pictograms) 6 ADR (Europe) (Pictograms) Protective Equipment Gloves. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Wear appropriate respirator when ventilation is inadequate. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 静脉-大鼠 LD50: 5.6 毫克/公斤; 静脉-小鼠 LD50: 7.3 毫克/公斤 CHEMICAL IDENTIFICATION RTECS NUMBER : TK6060000 CHEMICAL NAME : 2',6'-Pipecoloxylidide, 1-butyl- CAS REGISTRY NUMBER : 2180-92-9 LAST UPDATED : 199612 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C18-H28-N2-O MOLECULAR WEIGHT : 288.48 WISWESSER LINE NOTATION : T6NTJ A4 BVMR B1 F1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 4300 ug/kg TOXIC EFFECTS : Vascular - measurement of regional blood flow Behavioral - euphoria REFERENCE : AANEAB Acta Anaesthesiologica Scandinavica. (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.1- 1957- Volume(issue)/page/year: 21,521,1977 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 47 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3632766 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 5600 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 31,273,1972 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 35 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3632766 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 7100 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3632766 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 1620 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AACRAT Anesthesia and Analgesia (New York). (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.36- 1957- Volume(issue)/page/year: 64,209,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 64 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intratracheal SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 12500 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 26,78,1976 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 36600 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3632766 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intracervical DOSE : 500 ug/kg SEX/DURATION : female 39 week(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system REFERENCE : JPEMAO Journal of Perinatal Medicine. (Walter de Gruyter, Inc., 200 Saw Mill River Rd., Hawthorne, NY 10532) V.1- 1973- Volume(issue)/page/year: 12,75,1984 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraspinal DOSE : 2396 mg/kg SEX/DURATION : female 39 week(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - behavioral Reproductive - Effects on Newborn - other postnatal measures or effects REFERENCE : BJOGAS British Journal of Obstetrics and Gynaecology. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.82- 1975- Volume(issue)/page/year: 88,407,1981

安全

• 危害码 (欧洲): T+:Verytoxic;
• 风险声明 (欧洲): R26/27/28;R38;R41
• 安全声明 (欧洲): S22-S26-S36/37/39-S45
• 危险品运输编码: 2811

制备

左布比卡因的制备：消旋的布比卡因和L-(+)-酒石酸溶于丙酮，在室温搅拌至固体全溶，加入右布比卡因酒石酸盐，搅拌至右布比卡因酒石酸盐完全沉淀出。过滤出固体，在滤液中加入左布比卡因酒石酸盐，搅拌使左布比卡因酒石酸盐沉淀析出。过滤出固体，往滤液中加入消旋的布比卡因，加入丙酮，搅拌至固体全
溶。加入右布比卡因酒石酸盐晶种，搅拌约7h，如此不断进行下去。每次得右布比卡因酒石酸盐和左布比卡因酒石酸盐。在搅拌下，将左布比卡因酒石酸盐溶于水，用浓氨水调节pH值。过滤、水洗、干燥至恒重，得粗左布比卡因，用热异丙醇重结晶，得纯左布比卡因。