Quinine 奎宁

CAS 130-95-0 MFCD00198096

化学结构图

130-95-0
SMILES: C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12

化学属性

Mol. FormulaC20H24N2O2
Mol. Weight324.42
Melting Point173-175°C
TSCAYes
Solubility略溶于水
Density1.21
Stability对光线、湿度敏感
Boiling Point462.75 °C at 760 mmHg

别名和识别编码

Chemical NameQuinine
MDL NumberMFCD00198096
CAS Number130-95-0
Beilstein Registry Number91867
EC Number205-003-2
Merck Number8061
PubChem Substance ID3034034
Synonym Quinine {LY} Quinine {} {LY} Quinine {} {} {LY} Quinine {} {} {} {LY} Quinine {} {} {} {} {LY} Quinine {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Quinine {} {} {} {} {} {} {} {} {} {} {}
Chemical Name Translation奎宁
Reaxys-RN5293630
Wiswesser Line NotationT66 BNJ HO1 EYQ- DT66 A B CNTJ A1U1
LabNetwork Molecule IDLN00240012
InChIInChI=1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1
Canonical SMILESO[C@H](C1=CC=NC2=C1C=C(OC)C=C2)[C@@]3([H])[N@](C[C@@H]4C=C)CC[C@H]4C3
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分类

  • {SNA} Alphabetical, Analytical Standards, Certified Reference Materials (CRMs), Chromatography, Cinchona, Fluka CRMs for Chromatography (neats), Life Sciences Standards, N - R, Natural Products, Nitrogen containing compounds, Organic CRMs Alphabetical, Organic CRMs TraceCERT, Phytopharma Standards, Standards by Plant Genus, Substance Classification, 分析/色谱
  • {SNA} Alkaloid, Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Chiral Resolution Reagents, Chiral Resolving Reagents, Cinchona Alkaloids, Ion Channels,
  • {SNA} Alkaloid,

产品应用

  • 钾离子通道阻断剂。手性催化剂,用于高异构体选择性[2+2]环加成反应;二乙基锌添加到醛上。

相关文献及参考

  • Resolving agent for chiral acids. For a review of resolutions, see: Topics Stereochem., 6, 107 (1977).
  • Merck: 14,8061
  • Merck: 14,8061 Beilstein:23(2)416

安全信息

GHS Symbol
WGK Germany3
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P284 Wear respiratory protection.? 佩戴呼吸保护装置。
  • P301+P312+P330
  • P302+P350
  • P302+P352+P333+P313+P362+P364
  • P305+P351+P338
  • P337+P313
  • P342+P311
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled 吸入可能导致过敏或哮喘症状或呼吸困难
  • H302 Harmful if swallowed 吞食有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
RTECSVA6020000
Signal word Danger
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24 Avoid contact with skin 避免皮肤接触;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套;
  • S37 Wear suitable gloves 戴适当手套;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R36/38 Irritating to eyes and skin 对眼睛和皮肤有刺激性
  • R42/43
Storage condition 2-8°C, protect from light, stored under nitrogen {LY} 2-8°C, protect from light, stored under nitrogen Light Sensitive {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light, stored under nitrogen {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from l
Hazard Codes Xn Xn,Xi
Packing GroupIII
Hazard Class6.1(b)
UN Number 1544
TYPE OF TEST            : LDLo - Lowest publi

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 74 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - visual field changes
   Sense Organs and Special Senses (Ear) - tinnitus
   Gastrointestinal - nausea or vomiting
REFERENCE :
   AJOPAA American Journal of Ophthalmology.  (Ophthalmic Pub. Co., 435 N.
   Michigan Ave., Suite 1415, Chicago, IL 60611)  Series 3: V.1-    1918-
   Volume(issue)/page/year: 90,403,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 115 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-

{

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 68 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg.,
   2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan)  V.1-   1988-
   Volume(issue)/page/year: 4,105,1991

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - guinea pig
DOSE/DURATION           : 1800 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   SMWOAS Schweizerische Medizinische Wochenschrift.  (Schwabe & Co.,
   Steintorst 13, 4010 Basel, Switzerland)  V.50-    1920-
   Volume(issue)/page/

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Mammal - species unspecified Lymphocyte
DOSE/DURATION           : 100 umol/L
REFERENCE :
   PMSBA4 Progress in Molecular and Subcellular Biology.  (Springer-Verlag,
   Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.)  V.1-    1969-
   Volume(issue)/page/year: 2,134,1971

TYPE OF TEST            : DNA adduct
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 30 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 89,95,1981

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 650 mg/kg
SEX/DURATION            : female 4-8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
   ARPTAF Arkhiv Patologii.  Archives of Pathology.  (V/O Mezhdunarodnaya
   Kniga, 113095 Moscow, USSR) V.8-    1946-  Volume(issue)/page/year:
   20(12),64,1958

TYPE OF TEST            : TDLo - Lowest publi

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE                    : 280 mg/kg
SEX/DURATION            : female 7-8 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
REFERENCE :
   ARPTAF Arkhiv Patologii.  Archives of Pathology.  (V/O Mezhdunarodnaya
   Kniga, 113095 Moscow, USSR) V.8-    1946-  Volume(issue)/page/year:
   20(12),64,1958

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSU

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 60 mg/kg
SEX/DURATION            : female 7 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - Central Nervous System
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
   Reproductive - Specific Developmental Abnormalities - hepatobiliary system
REFERENCE :
   ARKIAP Archiv fuer Kinderheilkunde.  (Stuttgart, Fed

其他信息

  • 比旋光度:-172 ° (c=1, EtOH)
  • 下游产品:(S)-1,1-螺二氢茚-7
  • Alfa Aesar:无水奎宁,99%(totalbase),maycont.upto5%dihydroquinine Quinine, anhydrous, 99% (total base), may cont. up to 5% dihydroquinine(130-95-0)
  • www.aladdin-reagent.com奎宁是一种喹啉型生物碱。存在于茜草科金鸡纳树皮中。二盐酸奎宁的熔点180~185℃,易溶于水、乙醇;奎宁硫酸盐的熔点235.2℃。为金鸡纳树皮中存在的主要生物碱。白色颗粒状或微晶性粉末,微风化性。无臭,味微苦。微溶于水和甘油,易溶于乙醇,氯仿,溶于稀酸、稀氨水中。在硫酸中呈强蓝色荧光。与许多酸易生成盐。 熔点:173~177℃ 比旋光度:-145.2°(乙醇)
  • 理化性质:奎宁又名金鸡纳霜、金鸡纳碱,是茜草科植物金鸡纳树及其同属植物的树皮中的主要生物碱,金鸡纳树皮含有20多种生物碱,除奎宁外,有抗疟作用的还有奎尼丁、辛可宁及辛可尼丁等。以金鸡纳树皮的全部生物碱作抗疟药和解热药,称金鸡纳全碱或全奎宁。奎宁化学上属喹啉类,与奎尼丁互为异构体。白色无定形粉末或结晶,无臭,味极苦。熔点172.8℃,有左旋光性,[α]D20-168°(乙醇) 。溶于乙醇、氯仿、苯、乙醚,微溶于水。其稀硫酸溶液有蓝色荧光,滴加溴水及过量氨水,即显翠绿色。将金鸡纳树皮粉以石灰与氢氧化钠处理,煤油提取,稀硫酸中和,将析出的硫酸奎宁与氨作用即得。也可以间羟基苯甲醛与α-氨基乙醛为原料合成。用于治疗和预防各种疟疾,药用为其硫酸盐或盐酸盐
  • 用途二:钾离子通道阻断剂。手性催化剂,用于高异构体选择性[2+2]环加成反应;二乙基锌添加到醛上。
  • 不良反应:1,金鸡纳反应:每日奎宁用量超过1g或稍久即可出现,表现为恶心、呕吐、耳鸣、头痛、视力听力减退,停药后一般可恢复。 2,特异质反应:可见急性溶血、皮炎、瘙痒、血管神经性水肿及支气管哮喘等。少数恶性疟患者小剂量奎宁可见寒战、高热、呕吐、血红蛋白尿、尿闭等急性溶血症,称黑尿热,严重者可致死。 3,静脉推注,可抑制心脏引起血压下降,甚至休克危及生命,故严禁静脉推注。静滴也应慎用。肌注易致组织坏死,除不能口服外,一般不用。
  • 检测方法:HPLC,Rotation
  • F:8
  • 奎宁价格(试剂级):更新日期 产
  • Sigma Aldrich:130-95-0(sigmaaldrich)
  • 注意事项:1.大剂量易致第八对脑神经及视神经损害,耳聋、前庭障碍、视神经炎患者禁用。患有急性静脉炎、肾炎、糖尿病、心血管疾病、心动过缓、房室传导阻滞者禁用。大剂量可致畸和有兴奋子宫平滑肌作用. 经期妇女、孕妇禁用。可降低骨骼肌兴奋性,故重症肌无力者禁用。 2.有抑制心脏作用,静脉推注易致休克,不宜采用; 静滴宜密切观察血压变化; 肌注可引起组织坏死,宜采用深部臀肌注射。禁与奎尼丁、氯喹等同时并用,以免引起心脏骤停。
  • 外观性质:白色颗粒状或微晶性粉末,微风化性。无臭,味微苦。微溶于水和甘油,易溶于乙
  • 理化性质:奎宁又名金鸡纳霜、金鸡纳碱,是茜草科植物金鸡纳树及其同属植物的树皮中的主要生物碱,金鸡纳树皮含有20多种生物碱,除奎宁外,有抗疟作用的还有奎尼丁、辛可宁及辛可尼丁等。以金鸡纳树皮的全部生物碱作抗疟药和解热药,称金鸡纳全碱或全奎宁。奎宁化学上属喹啉类,与奎尼丁互为异构体。白
  • 奎宁价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 61004083 奎宁;金鸡纳碱;规宁;鸡钠碱;金鸡纳霜 10g 175元 2011/08/23 xw020107 奎宁;金鸡纳碱;规宁;鸡钠碱;金鸡纳霜 10g 150元 2011/08/23 6
  • Quinine is a primary alkaloid of various species of Cinchona, optical isomer of Quinidine and an anti-malarial, skeletal, muscle relaxant.
  • {Chemi

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