辛可尼丁 | 485-71-2

• 物质功能分类: 原料药 - 抗生素类药物 - 其它抗生素类药
• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 中文名称: 辛可尼丁
• 中文别名: 辛可尼定；(9S)-6'-甲氧基辛可宁-9-醇；类金鸡纳碱；金鸡尼丁；辛可尼啶；4-喹啉基-(5-乙烯基-1-氮杂双环[2.2.2]辛烷-2-基)甲醇；(9S)-6"-甲氧基辛可宁-9-醇
• 英文名称: Cinchonidin
• 英文别名: Cinchonidine；(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
• CAS: 485-71-2
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: KMPWYEUPVWOPIM-KODHJQJWSA-N

物化性质

• 熔点：
  204-206 °C(lit.)
• 比旋光度：
  -115 º (c=1, EtOH)
• 沸点：
  436.16°C (rough estimate)
• 密度：
  1.0863 (rough estimate)
• 溶解度：
  0.25克/升
• LogP：
  2.68 at 25℃
• 碰撞截面：
  168.2 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
• 稳定性/保质期：

  按规格使用和贮存，不会发生分解，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2939200000
• 包装等级：
  III
• 危险类别：
  6.1(b)
• 危险品运输编号：
  UN 1544
• 储存条件：
  密封保存，并置于通风、干燥的地方，避免与氧化物接触。

SDS

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

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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.

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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.

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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:

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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.

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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.

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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.

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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.

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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

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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.

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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.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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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.

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

辛可尼丁是一种喹啉型生物碱，属于金鸡纳生物碱的一种，又称金鸡尼丁，是辛可宁的立体异构体。它在醚中结晶为白色针状或棱形晶体，熔点为204～206℃，比旋光度-115°（乙醇，C＝1），折射率-107.5°（乙醇，C＝1）。辛可尼丁能溶于醇、醚、丙酮、苯和氯仿，几乎不溶于冷水。

应用

辛可尼丁作为有机合成中间体和医药中间体，在实验室有机合成过程中和化工医药研发中被广泛应用。

作用

辛可尼丁与奎宁相似，具有抗疟疾的作用。在从金鸡纳树皮提取液中分离出奎宁后，可以通过碱处理母液，并加入酒石酸使其生成难溶的酒石酸盐来分离出生物碱。

结构特点

金鸡纳碱（如奎宁、奎尼丁、辛可宁和辛可尼丁等）是一类在约两个世纪前从金鸡纳树皮中发现的重要天然产物。在过去，它们是治疗疟疾的特效药；近年来，在不对称合成中作为催化剂的优势骨架得到了广泛认可。从生物合成的角度来看，金鸡纳生物碱是由单萜吲哚生物碱衍生而来。

生物活性

Cinchonidine是一种生物碱，在有机化学中用于不对称合成。

靶点

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

体外研究

• Cinchonidine（α-Quinidine）是金鸡纳树皮和甘果木中发现的生物碱，被用作有机化学中的不对称合成基块。它是一个弱的血清素转运蛋白（SERT）抑制剂，具有以下Ki值：dSERT 330 μM, hSERT 4.2 μM, hSERT I172M 36 μM, hSERT S438T 196 μM, hSERT Y95F 15 μM。