Carbamazepine 卡马西平

CAS 298-46-4 MFCD00005073

化学结构图

298-46-4
SMILES: NC(=O)N1C2=CC=CC=C2C=CC2C=CC=CC1=2

化学属性

Mol. FormulaC15H12N2O
Mol. Weight236.26858
Melting Point189-192°C
Density1.422
SolubilityDMSO 47 mg/mL Water <1 mg/mL Ethanol 18 mg/mL
Appearance 白色或类白色结晶性粉末。熔点204-206℃(190-193℃)。溶于乙醇、丙酮、丙二醇,不溶于水。无臭,无味。
Boiling Point411°C at 760 mmHg

别名和识别编码

Chemical NameCarbamazepine
CAS Number298-46-4
Synonym Carbamazepine {LY} Carbamazepine {} {LY} Carbamazepine {} {} {LY} Carbamazepine {} {} {} {LY} Carbamazepine {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Carbamazepine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID2554
EC Number206-062-7
MDL NumberMFCD00005073
Reaxys-RN1246090
Merck Number1781
Beilstein Registry Number1246090
Chemical Name Translation卡马西平
Wiswesser Line NotationT C676 BNJ BVZ
LabNetwork Molecule IDLN00238893
InChIInChI=1S/C15H12N2O/c16-15(18)17-13-7-3-1-5-11(13)9-10-12-6-2-4-8-14(12)17/h1-10H,(H2,16,18)
Canonical SMILESO=C(N1C2=CC=CC=C2C=CC3=CC=CC=C31)N
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分类

  • {SNA} APIs & Metabolites, APIs (Active Pharmaceutical Ingredients) & Metabolites, Additional Standards, Analytical Standards, Carbamazepine, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards, Pharmacopeia Metrological Institutes Standards, Secondary Standards, 分析/色谱
  • {SNA} Approved Therapeutics/Drug Candidates, Benzodiazepines and Anxiolytics, Bioactive Small Molecules, C-CH, Cell Biology, Cell Signaling and Neuroscience, GABA and Glycine Receptor Modulators, Ion Channels,
  • Bioactive Small Molecules, C-CH, Cell Biology, Cell Signaling and Neuroscience, Core Bioreagents,
  • {SNA} Analytical Standards,
  • {SNA} Analytical Standards,

产品应用

  • 镇惊剂;配体,用于GABAA受体的苯并二氮杂调节位点。钠离子通道抑制剂。

相关文献及参考

  • Stenger, E.G., et al.: Med. Exp., 11, 191 (1964),
  • Pynnonen, S., et al.: Ther. Drug Monit., 1, 409 (1979),
  • Ichikawa, J., Valproate and carbamazepine increase prefrontal dopamine release by 5-HT 1A receptor activation. Eur. J. Pharmacol. 380 , R1-3, (1999) 摘要
  • Afanas'ev, I., Lamotrigine and carbamazepine affect differently the release of D- 3H aspartate from mouse cerebral cortex slices: involvement of NO. Neurochem. Res. 24 , 1153, (1999)
  • Merck 14 ,1781
  • Corp MSDS 1 , 680:A / FT-IR 2 (2), 3066:D / FT-NMR 1 (2), 1451:A / RegBook 1 (2), 2073:E / Sax 6 , 902 / Structure Index 1 , 328:C:5
  • Short: III/35B Title: Nuclear Magnetic Resonance (NMR) Data: Chemical Shifts and Coupling Constants for Fluorine-19 and Nitrogen-15 Author: Balasubramanian, M.; Gupta, R.R.; Jain, M.; Perumal, S. Editor: Gupta, R.R.; Lechner, M.D. Source: Landolt-Börnstein, New Series Volume: III/35B Year: 1998 ISBN: 3-540-63275-1 ISBN: 978-3-540-63275-7 Internet Resource: DOI:10.1007/b55685 RefComment: VII, 242 pages. With CD-ROM. Hardcover Abstract: This volume provides a comprehensive and evaluated compilation of nuclear magnetic resonance data. Chemical shifts and coupling constants of boron-11 and phosphorus-31 (subvol. A), fluorine-19 and nitrogen-15 (subvol. B), hydrogen-1 (subvol. C), and carbon-13 (subvol. D) compounds are tabulated together with the gross- and structure formulas and the most readily available solvents. Due to the large amount of the data merely chemical shifts are presented in the printed versions, and all the data, chemical shifts and coupling constants are provided on CO-ROM's.
  • Short: EINECS Title: EINECS (European Inventory of Existing Commercial Chemical Substances) Source: Official Journal of the European Communities Volume: C 146 A (15.06.1990) Page: 1 Year: 1990 Internet Resource: http://ecb.jrc.ec.europa.eu/esis/i

安全信息

GHS Symbol
WGK Germany2
Hazard Codes Xn
Hazard statements
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H302 Harmful if swallowed 吞食有害
  • 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
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Faceshields, Gloves
RTECSHN8225000
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • 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。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西,喝水或吸烟。
  • 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。
  • P301+P312+P330
  • P305+P351+P338
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P342+P311
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R42/43
Packing GroupIII
Storage condition 2-8°C {LY} 2-8°C {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Hazard Class6.1(b)
UN Number 3249
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 158 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans
   Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium)  V.4-   
   1898-  Volume(issue)/page/year: 202,106,1973

TYPE OF TEST            : TD

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 253 mg/kg/6W-I
TOXIC EFFECTS :
   Gastrointestinal - nausea or vomiting
   Liver - liver function tests impaired
REFERENCE :
   JCPYDR Journal of Clinical Pyschopharmacology.  (Williams & Wilkins Co., 428
   E. Preston St., Baltimore, MD 21202)  V.1-    1981- Volume(issue)/page/year:
   6,251,1986

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human
DOSE/DURATION           : 43 mg/kg
TOXIC EFFECTS :
   Behavioral - sleep
   Behavioral - hallucinations, distorted perceptions
   Gastrointestinal - nausea or vomiting
REFERENCE :
   BMJOAE British Medical Journal.  (British Medical Assoc., BMA House,
   Tavistock Sq., London WC1H 9JR, UK)  V.1-    1857- Volume(issue)/page/year:
   1,754,1977

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >1500 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: 30,477,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 4800 mg/kg
SEX/DURATION            : female 7-18 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - other developmental
   abnormalities
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 41,311,1990

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE                    : 1288 mg/kg
SEX/DURATION            : female 26-42 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - skin and skin
   appendages
REFERENCE :
   NRPDDB Neuropediatrics (Stuttgart). (Hippokrates Verlag GmbH, Postfach 593,
   D-7000 Stuttgart 1, Fed. Rep. Ger.)  V.11-    1980- Volume(issue)/page/year:
   16,167,1985

{h

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 440 mg/kg
SEX/DURATION            : female 6-16 day(s) after conceptio

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 5628 mg/kg
SEX/DURATION            : female 7-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - eye/ear
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 23,33A,1981

其他信息

  • MOL 文件:298-46-4.mol
  • 图谱信息:卡马西平(298-46-4)红外图谱(IR2) 卡马西平(298-46-4)质谱(MS) 卡马西平(298-46-4)红外图谱(IR1) 卡马西平(298-46-4)核磁图( 1 HNMR)
  • 方法一:先由邻硝基甲苯经缩合、还原、环合制得10,11-二氢-5H-二苯并[b,f]氮杂 ,然后经消除、酰化制得该品,或经氯甲酰化、溴化、消除、胺化而得。1.10,11-二氢-5H-二苯并[b,f]氮杂 的制备将甲醇钠和石油醚的混合物冷却,滴加邻硝基甲苯和甲酸乙酯混合液,用稀盐酸调节至pH5-6,2,2'-二硝基联苯。将其溶于乙醇滴加盐酸-乙醇,同时徐徐加入铁粉。用氢氧化钠调至pH8-9过滤,滤液用磷酸调至pH5,析出结晶,得2,2'二氨基联苄磷酸盐。在搅拌下将2,2'二氨基联苄磷酸盐加热至熔融,将物料放入水中析出结晶,得10,11-二氢-5H-二苯并[b,f]氮杂粗品。粗品用石油醚重结晶,得精品。2.卡巴西平的制备方法一将反应床的铁催化剂用热风活化后,控制床温在400-450℃,通入过热蒸汽,慢慢加入熔融的10,11-二氢-5H二苯并[b,f]氮杂,反应产物通过吸收塔用水喷淋吸收,收集塔下浮出的固体,吸滤,干燥得粗品。用乙醇重结晶,得5H二苯并[b,f]氮杂 精品。然后,以苯为溶剂,将5H二苯并[b,f]氮杂 与异氰酸反应再用氢氧化钠溶液调至pH12-14,回流,把温度降至10℃以下,析出结晶,过滤,水洗,干燥,得到卡马西平粗品。粗品用乙醇重结晶、活性炭脱色,即为成品。方法二将10,11-二氢-5H二苯并[b,f]氮杂和甲苯加入反应锅,搅拌加热溶解。回流下通光气,通完后继续回流使氯甲酰化反应完全混合。减压蒸出一部分甲苯,冷却析出结晶,过滤,干燥,得5-氯甲酰基-10,11-二氢二苯并[b,f]氮杂 。将其加入氯苯中,再加入过氧化苯甲酰,加热滴加溴素,加毕,反应至无溴化氢气体逸出为止。将上述反应液趁热转入热乙醇中,通氨,消除、胺化反应结束析出大量固体。蒸除乙醇使反应液呈糊状,加水,过滤,即得粗品。粗品经乙醇重结晶,活性炭脱色,得到卡巴西平成品。
  • Sigma Aldrich:298-46-4(sigmaaldrich)
  • Acros Organics:卡马西平 Carbamazepine, 99%(298-46-4)
  • 上游原料:2-硝基甲苯 --> 亚氨基芪 --> EDTA
  • 用途一:抗惊厥药,用于治疗癫痫大发作和精神运动性癫痫,还可治疗三叉神经痛
  • TCI Shanghai:卡马西平 Carbamazepin,>;97.0%(N)(298-46-4)
  • MSDS 信息:Carbamazepine(298-46-4).msds
  • 用途二:卡巴西平属二苯并氮杂 类抗癫痫药,具有与苯妥英钠相似的抗癫痫作用。对精神运动性发作最有效,对大发作、局限性发作和混合型发作也有效。本品抗外周神经痛作用优于苯妥英钠,可用于三叉神经痛和舌咽神经痛。也可用于心律失常及尿崩等症的治疗。小鼠口服LD50为3750mg/kg,大鼠为4025mg/kg。
  • 卡马西平价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 C1095 卡马西平 Carbamazepin 10G 200元 2014/06/02 C1095 卡马西平 Carbamazepin 25G 400元 2010/06/21 344360010 卡马西平 Carbamazepine 99% 1 GR 200元

系列性分类


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