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

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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