485-71-2

• 常用中文名：辛可尼定
• 常用英文名：Cinchonidine
• CAS号：485-71-2
• 分子式：C₁₉H₂₂N₂O
• 分子量：294.391
• 相关类别： 原料药 抗生素类药物 其它抗生素类药
• 发布时间：2018-07-23 12:25:05
• 更新时间：2024-01-02 17:51:08
• Cinchonidine (α-Quinidine) 是在金鸡纳和角蒿中发现的金鸡纳生物碱。 Cinchonidine (α-Quinidine) 是用于有机化学中不对称合成的砌块。是血清素转运蛋白 (SERT)的弱抑制剂,对于dSERT,hSERT,hSERT I172M,hSERT S438T,hSERT Y95F的 Ki 分别为330,4.2,36,196,15 μM。有抗疟活性[1].。

名称

• 中文名: 辛可尼丁
• 英文名: cinchonidine
• 中文别名: 金鸡尼丁; 4-喹啉基-(5-乙烯基-1-氮杂双环[2.2.2]辛烷-2-基)甲醇; 辛可尼定; (9S)-6'-甲氧基辛可宁-9-醇; 类金鸡纳碱; 辛可尼啶
• 英文别名: (+)-cinchonine; (R)-4-Quinolinyl[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol; L-CINCHONIDINE; Cinchonan-9-ol, (8α,9R)-; (R)-4-Chinolinyl[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol; (-)-CINCHONIDINE; (R)-[(2S,4S,5R)-5-éthènyl-1-azabicyclo[2.2.2]oct-2-yl](4-quinoléinyl)méthanol; α-Quinidine; Cinchondine; Cinchovatine; MFCD00006783; Cinchonidine; 1-Cinchonidine; EINECS 207-622-3; chinchonidine; a-quinidine; (8α,9R)-Cinchonan-9-ol; (8a,9R)-Cinchonan-9-ol; Cinchovatine (VAN); TCMDC-123934

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 464.5±30.0 °C at 760 mmHg
• 熔点: 204-206ºC
• 分子式: C₁₉H₂₂N₂O
• 分子量: 294.391
• 闪点: 234.7±24.6 °C
• 精确质量: 294.173218
• PSA: 36.36000
• LogP: 3.35
• 外观性状: 白色粉末
• 蒸汽压: 0.0±1.2 mmHg at 25°C
• 折射率: 1.652
• 储存条件:

  密封保存，放置于通风、干燥地方，避免于其他氧化物接触。

• 稳定性:

  按规格使用和贮存，不会发生分解，避免与氧化物接触

• 水溶解性: 水溶性：不溶；可溶于：醇,氯仿,乙醚
• 分子结构:

  1、 摩尔折射率：89.42

  2、 摩尔体积（m³/mol）：244.5

  3、 等张比容（90.2K）：670.1

  4、 表面张力（dyne/cm）：56.3

  5、 极化率（10 ^-24 cm ³）：35.45

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：2.7

  2、 氢键供体数量：1

  3、 氢键受体数量：3

  4、 可旋转化学键数量：3

  5、 互变异构体数量：未确定

  6、 拓扑分子极性表面积（TPSA）：36.4

  7、 重原子数量：22

  8、 表面电荷：0

  9、 复杂度：412

  10、 同位素原子数量：0

  11、 确定原子立构中心数量：4

  12、 不确定原子立构中心数量：0

  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：白色斜方片状或棱形结晶

  2. 密度（g/ m³,25/4℃）：未确定

  3. 相对蒸汽密度（g/cm³,空气=1）：未确定

  4. 熔点（ºC）：204-206

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：-107.5

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：-115

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：难溶于水

生物活性

• 描述: Cinchonidine (α-Quinidine) 是在金鸡纳和角蒿中发现的金鸡纳生物碱。 Cinchonidine (α-Quinidine) 是用于有机化学中不对称合成的砌块。是血清素转运蛋白 (SERT)的弱抑制剂,对于dSERT,hSERT,hSERT I172M,hSERT S438T,hSERT Y95F的 Ki 分别为330,4.2,36,196,15 μM。有抗疟活性[1].。
• 相关类别:
  信号通路 >> 神经信号通路 >> 5-羟色胺转运蛋白
  天然产物 >> 生物碱
  研究领域 >> 感染
• 靶点:

  Ki: 330 μM (dSERT), 4.2 μM (hSERT), 36 μM (hSERT I172M), 196 μM (hSERT S438T), 15 μM (hSERT Y95F) [1]

• 体外研究: 辛可尼定(α-奎尼丁)是在金鸡纳和角蒿中发现的金鸡纳生物碱。用于有机化学中不对称合成的结构单元。对于dSERT,hSERT,hSERT I172M,hSERT S438T,hSERT Y95F,血清素转运蛋白(SERT)的弱抑制剂Kis分别为330,4.2,36,196,15μM[1]。
• 参考文献:

  [1]. Beckman ML, et al. Stereoselective inhibition of serotonin transporters by antimalarial compounds. Neurochem Int. 2014 Jul;73:98-106.

MSDS

Name: Cinchonidine 98.5-101% (On The Dried Substance) Material Safety Data Sheet Synonym: Alpha-Quinidine CAS: 485-71-2 Section 1 - Chemical Product MSDS Name:Cinchonidine 98.5-101% (On The Dried Substance) Material Safety Data Sheet Synonym:Alpha-Quinidine Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 485-71-2 Cinchonidine 98% 207-622-3 Hazard Symbols: None Listed. Risk Phrases: None Listed. Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Light sensitive.The toxicological properties of this material have not been fully investigated. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Chronic: No information found. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution. Extinguishing Media: Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 485-71-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: white to cream Odor: None reported. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 200.00 - 203.00 deg C Autoignition Temperature: Not applicable. Flash Point: Not applicable. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: practically insoluble in water Specific Gravity/Density: Molecular Formula: C19H22N2O Molecular Weight: 294.39 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, light, dust generation, excess heat, strong oxidants. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen. Hazardous Polymerization: Has not been reported. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 485-71-2: GD2975000 LD50/LC50: Not available. Carcinogenicity: Cinchonidine - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: Not available. Risk Phrases: Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 28A After contact with skin, wash immediately with plenty of water. S 37 Wear suitable gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 485-71-2: 2 Canada CAS# 485-71-2 is listed on Canada's NDSL List. CAS# 485-71-2 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 485-71-2 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 急性毒性：大鼠经腹腔LD50：206mg/kg，嗜睡（普通抑郁活动），肌肉收缩或痉挛； 鹌鹑经口LD50：>316mg/kg，除致死剂量外无详细说明。 生态学数据: 该物质对环境可能有危害，对水体应给予特别注意。 CHEMICAL IDENTIFICATION RTECS NUMBER : GD2975000 CHEMICAL NAME : Cinchonidine CAS REGISTRY NUMBER : 485-71-2 LAST UPDATED : 199701 DATA ITEMS CITED : 3 MOLECULAR FORMULA : C19-H22-N2-O MOLECULAR WEIGHT : 294.43 WISWESSER LINE NOTATION : T66 BNJ EYQ- DT66 A B CNTJ A1U1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 206 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 4,265,1948 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Bird - quail DOSE/DURATION : >316 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : EESADV Ecotoxicology and Environmental Safety. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1977- Volume(issue)/page/year: 6,149,1982

安全

• 符号: GHS07, GHS08
• 信号词: Warning
• 危害声明: H302-H317-H361d-H373
• 警示性声明: P280
• 靶器官: Heart, Immune system
• 个人防护装备: Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): Xn:Harmful;
• 风险声明 (欧洲): R20/21/22
• 安全声明 (欧洲): S36/37
• 危险品运输编码: UN 1544
• WGK德国: 3
• RTECS号: GD2975000
• 包装等级: III
• 危险类别: 6.1(b)
• 海关编码: 2939200000

合成路线

71-41-0 118-10-5 ~% 118-10-5 485-71-2 详细

文献：Rabe Justus Liebigs Annalen der Chemie, 1932 , vol. 492, p. 242,255

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