Phenacetin 非那西丁

CAS 62-44-2 MFCD00009094

化学结构图

62-44-2
SMILES: CCOc1ccc(NC(C)=O)cc1

化学属性

Mol. FormulaC10H13NO2
Mol. Weight179
Melting Point133-136
TSCAYes
Solubility0.076 G/100 ML
Boiling Point132°C/4mmHg
Appearance powder
Density1.099

别名和识别编码

Chemical NamePhenacetin
CAS Number62-44-2
Synonym N-(4-Ethoxy-phenyl)-acetamide P-ACETOPHENETIDIDE N-(4-ethoxyphenyl)ethanamide N-ACETYL-P-PHENETIDIN ACETOPHENETIDIN ######## {uni_hamburg} ASA compound ACET-P-PHENETIDINE Phenazetin Darvon compound N-ACETYL-P-PHENETIDINE 4-Ethoxyacetanilide Edrisal N-Acetyl-p-phenetidine Pyrroxate 非那西丁 Fenidina phenacetin p-Acetophenetidine {Chem {Chemi phenacetin (INN) {uni_hambu Pyraphen p-Acetphenetidin {uni_hambur Acetophenetidine Em Viden Aceto-para-phenalide Sinubid Acet-p-phenetidin Acetyl Pa Dasin CH Synalog
MDL NumberMFCD00009094
PubChem Substance ID4754
Beilstein Registry Number1869238
EC Number200-533-0
Merck Number7204
Reaxys-RN1869238
Chemical Name Translation非那西丁
Wiswesser Line Notation2OR DMV1
LabNetwork Molecule IDLN00194554
InChIInChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12)
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分类

  • {SNA} Analytical Standards,
  • {SNA} Bioactive Small Molecules, Building Blocks, Cell Biology, Chemical Synthesis,
  • {SNA} Analytic
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, Pharmaceutical Secondary Standards, Pharmaceutical Standards
  • {SA} Bioactive Small Molecules, Building Blocks, Cell Biology, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks, P, Protected Amines
  • {SNA} Bioactive Small Molecules, Building Blocks, Chemical Synthesis, Nitrogen Compounds, Organic Building Blocks, P, Protected Amines, 细胞生物学
  • Pharmaceuticals
  • {SNA} Building Blocks, Chemical Synthesis,

产品应用

  • CYP1A2 和 CYP2D6 的底物。

相关文献及参考

  • Short: III/35E
  • Boyd, et al.: Toxicol. Appl. Pharmacol., 1, 240 (1959),
  • Short: IV/1a
  • Short: IV/20B
  • Merck: 14,7204 Beilstein:13(4)1092
  • Dubach, C.U., et al.: N. Engl. J. Med., 308, 357 (1983),
  • Merck: 14,7204

安全信息

WGK Germany3
GHS Symbol
Precautionary statements
  • P308+P313
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P405 Store locked up. 上锁保管。
  • P263 Avoid contact during pregnancy/while nursing. 怀孕/哺乳期间避免接触。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • 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。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
Hazard statements
  • H350 May cause cancer 可能致癌
  • H302 Harmful if swallowed 吞食有害
RTECSAM4375000
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
Signal word
Safety Statements
  • 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）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
Risk Statements
Storage condition 2-8°C Hygroscopic
Hazard Codes T 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1008 gm/kg/96W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - tumors
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   IJCNAW International Journal of Cancer.  (International Union Against
   Cancer, 3 rue du Conseil- General, 1205 Geneva, Switzerland)  V.1-    1966-
   Volume(issue)/page/year: 29,439,1982

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 572 gm/kg/60W-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Sense Organs and Special Senses (Olfaction) - tumors
   Kidney, Ureter, Bladder - tumors
REFERENCE :
   GANNA2 Gann.  Japanese Journal of Cancer Research.  (Tokyo, Japan)  V.1-75,
   1907-84.  For publisher information, see JJCREP.  Volume(issue)/page/year:
   70,29,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human
DOSE/DURATION           : 7300 mg/kg/Y-C
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   SJUNAS Scandinavian Journal of Urology and Nephrology.  (Almqvist & Wiksell,
   POB 45150, S-10430 Stockholm, Sweden)  V.1-    1967-
   Volume(issue)/page/year: 2,145,1968

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 140 gm/kg/13Y-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
   BJURAN British Journal of Urology.  (Longman Group Ltd., POB 11318,
   Birmingham, AL 35202) V.1-    1929-  Volum

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rabbit
DOSE/DURATION           : 1 gm/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
REFERENCE :
   ARZNAD Arzneimittel-Forschung. Drug Research.  (Editio Cantor Verlag,
   Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.)  V.1-    1951-
   Volume(issue)/page/year: 21,719,1971

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 74 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85DCAI "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M.,
   Springfield, IL, C.C. Thomas, 1970  Volume(issue)/page/year: 2,73,1970

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERV

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1625 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: 8,25,1958

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - hamster
DOSE/DURATION           : 1690 mg/kg
TOXIC EFFECTS :
   Behavioral - ataxia
   Behavioral - coma
   Cardiac - pulse rate increase, without fall in BP
REFERENCE :
   PHARAT Pharmazie.  (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18,
   Berlin DDR-1020, Ger. Dem. Rep.)  V.1-    1946-  Volume(issue)/page/year:
   8,572,1953

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 263 gm/kg/17W (Continuous)
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 79,13,1980

{h

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 333 ug/plate
REFERENCE :
   IAPUDO IARC Publications.  (WHO Publications Centre USA, 49 Sheridan Ave.,
   Albany, NY 12210) No.27-    1979-  Volume(issue)/page/year: 27,283,1980

TYPE OF TEST            : DNA inhibition
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 20 gm/kg
REFERENCE :
   ARGEAR Archiv fuer Geschwulstforschung.  (VEB Verlag Volk und Gesundheit
   Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.)  V.1-    1949-
   Volume(issue)/page/year: 51,605,1981

TYPE OF TEST            : DNA damage
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 400 mg/kg
REFERENCE :
   ATSUDG Archives of Toxicology, Supplement.  (Springer-Verlag New York, Inc.,
   Service Center, 44 Hartz Way, Secaucus, NJ 07094)  No.1-    1978-
   Volume(issue)/page/year: 5,355,1982

TYPE OF TEST            : Host-mediated assay
TEST SYSTEM             : Rodent - rat Bacteria - Salmonella typhimurium
DOSE/DURATION           : 200 ug/kg
REFERENCE :
   ONCODU Revista de Chirurgui, Oncologie, Radiologie, ORL, Oftalmologie,
   Stomatologie, Seria: Oncologia.  (Rompresfilatelia, POB 12-201, Bucharest,
   Romania)  V.13(4)-    1974-  Volume(issue)/page/year: 19,183,1980

TYPE OF TEST            : DNA damage
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - rat
DOSE/DU

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 57200 mg/kg
SEX/DURATION            : male 20 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - spermatogenesis (incl. genetic material,
   sperm morphology, motility, and count)
REFERENCE :
   JCNDBK Journal of Clinical Pharmacology and New Drugs.  (Stamford, CT)
   V.11-13, 1971-73.  For publisher information, see JCPCBR.
   Volume(issue)/page/year: 11,96,1971

TYPE OF TEST            : TDL

{hazar

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 50336 mg/kg
SEX/DURATION            : male 17 week(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Fertility - male fertility index (e.g. # males impregnating
   females per # males exposed to fertile nonpregnant females)
REFERENCE :
   JCNDBK Journal of Clinical Pharmacology and New Drugs.  (Stamford, CT)
   V.11-13, 1971-73.  For publisher information, see JCPCBR.
   Volume(issue)/page/year: 11,96,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 6 gm/kg
SEX/DURATION            : female 1-20 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   KLWOAZ Klinische Wochenscrift.  (Springer-Verlag, Heidelberger Pl. 3, D-1000
   Berlin 33, Fed. Rep. Ger.)  V.1-    1922-  Volume(issue)/page/year:
   43,364,1965

其他信息

  • 用途二:对乙酰氨基苯乙醚用作有机合成原料及药物中间体。
  • Acros Org
  • 下游产品:
  • 图谱信息:非那西丁(62-44-2)红外图谱(IR1) 非那西丁(62-44-2)Raman光谱 非那西丁(62-44-2)核磁图( 13 CNMR) 非那西丁(62-44-2)红外图谱(IR2) 非那西丁(62-44-2)质谱(MS)
  • 本品为白色，无臭，味微苦。本品在乙醇或氯仿中溶解，在沸水中略溶，微溶于甘油。溶解度：1g/1310ml冷水、1g/82ml 、1g/15ml 冷乙醇、1g/2.8ml 沸乙醇、1g/14ml 氯仿、1g/90ml 醚。
  • 可燃性危险特性:明火可燃;加热分解释放有毒氮氧化物气体;该药副作用:苍白,肝受损,血红蛋白症
  • TCI Shanghai:对乙酰氨基苯乙醚 Phenacetin,>;98.0%(GC)(62-44-2)
  • Sigma Aldrich:62-44-2(sigmaaldrich)
  • 副作用:长期服用含非那西丁的制剂，可引起肾乳头坏死、间质性肾炎等，甚至可能诱发肾盂癌和膀胱癌。非那西丁还易使血红蛋白形成高铁血红蛋白，使血液携氧能力下降，引起紫绀反应。此外，非那西丁还可引起溶血和溶血性贫血，并对视网膜有一定毒性。长期服用非那西丁，还可造成对药物的依赖性。国外如美、英、德、日本等国家都决定取消非那西丁，或规定在其包装上须注明“不能长期服用或大剂量服用”。
  • 解热镇痛药:非那西丁的解热镇痛作用与“乙酰水杨酸”相似，主要用作解热镇痛药，作用缓慢而持久，对治疗头痛、神经痛、关节痛和发热等都有较好疗效，但抗风湿、消炎作用较弱。剂量过大可导致高铁血红蛋白症，造成机体缺氧，长期用药可损害肾脏，甚至引起乳头坏死，应慎用。因其毒副作用和其他同类药物的迅速发展，该药已停止单独使用，只是作为原料药和其他药物配复方制剂。常与阿司匹林、咖啡因一起组成复方阿司匹林，其组成为非那西丁0.162克，阿司匹林 0.227克，咖啡因0.035克，毒性较小，用于治疗伤风感冒。如在上述药物中加入少量扑尔敏，还可制成扑尔敏感冒片，可用于治疗感冒头痛、神经痛、风湿痛等。 非那西丁本身并无解热镇痛作用，在机体内，经过代谢分解出对乙酰氨基酚即扑热息痛，才发挥出解热镇痛的效果。还分解出对氨苯乙醚，对氨苯乙醚不但无解热镇痛作用，且是非那西丁毒副作用的主要因素。 中国于1954年开始生产非那西丁，由硝基氯苯与乙醇进行醚化反应得对硝基苯乙醚，再还原成对氨基苯乙醚后与乙酸进行乙酰化反应制得。
  • MOL 文件:62-44-2.mol
  • 方法一:(1)由对氨基苯乙醚经乙酰化而得。将苯、乙酐和对氨基苯乙醚的混合物，在油浴上加热共沸4h，反应完毕后冷却反应物，即析出非那汀，经过滤，冷苯洗涤，干燥即得，产量为理论量的86%。(2)由乙酰氨基苯酚与乙醇钠作用而得：先将对乙酰胺基苯酚加于乙醇钠中，再缓缓加入碘乙烷，加热回流1h，冷却，过滤，所得粗品溶于乙醇中，过滤，滤液用热水稀释，再经冷却,过滤，干燥，而得成品，产量为理论量的80%。第一个方法也可不用苯作溶剂，而用乙酸代替，工艺过程如下。将40%的稀乙酸加热至沸，投入对氨基苯乙醚，蒸去水，待温度升到150℃时加入冰醋酸，回流1h，继续蒸，待温度升至150℃以上，取样测定游离氨基苯乙醚，根据残余的氨基苯乙醚量加入乙酐，回流反应0.5h，检查终点，合格后减压，回收乙酸至氨基含量在0.046以下，含酸0.2%以下，将反应液压入热精制母液中，搅拌降温至40℃，过滤，得非那西汀粗品。精制，非那西汀粗品加沸水或精制母液，加热搅拌溶解，过滤，滤液用酸调节至pH=4.5-4.7，加入活性炭及硫代硫酸钠搅拌脱色，过滤，滤液冷却结晶，甩滤，气流干燥，得非那西汀。
  • 非那西丁价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2011/08/23 K7744001 菲那西汀 50g 239元 2011/04/16 P1669 非那西丁 Phenacetin 25G 11
  • 毒性分级:中毒
  • 用途一:解热镇痛药，用于治疗发热头痛、神经痛等
  • MSDS 信息:乙酰乙氧基苯胺(62-44-2).msds
  • 急性毒性:口服-大鼠 LD50:

系列性分类

  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. P - Bioactive Small Molecules
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Amides - Carbonyl Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Nitrogen Compounds 氮化合物
  5. Protected Amines - Nitrogen Compounds
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Nitrogen Compounds 氮化合物
  5. Protected Amines - Nitrogen Compounds
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Application Index - Enzymes, Inhibitors, and Substrates
  5. Cell Signaling Enzymes - Application Index
  6. Xenobiotics and Drug Metabolism - Cell Signaling Enzymes
  7. Substrates - Xenobiotics and Drug Metabolism
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Pharmaceutical Standards - Chromatography
  5. Pharmaceutical Secondary Standards - Pharmaceutical Standards
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Nitrogen Compounds 氮化合物
  5. Polyamines
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Multi-Drug Resistance and Drug Metabolism
  5. Drug and Xenobiotic Metabolism
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Cell Signaling Enzymes
  5. Xenobiotics and Drug Metabolism
  6. Inhibitors