61869-08-7

• 常用中文名：帕罗西汀
• 常用英文名：Paroxetine
• CAS号：61869-08-7
• 分子式：C₁₉H₂₀FNO₃
• 分子量：329.365
• 相关类别： 原料药 神经系统用药 抗抑郁、躁狂药
• 发布时间：2018-02-05 08:00:00
• 更新时间：2026-06-29 22:35:01
• 帕罗西汀是一种苯基哌啶衍生物,是一种有效的选择性血清素再摄取抑制剂(SSRI)。帕罗西汀是一种非常弱的去甲肾上腺素(NE)摄取抑制剂,但在这个部位,它仍然比其他SSRIs更有效[1]。

名称

• 中文名: 帕罗西汀
• 英文名: paroxetine
• 中文别名: 帕罗昔丁; (-)-反式-4-(4-氟苯基)-3-{[(3',4'-亚甲二氧基)苯氧基]甲基}-哌啶; 布洛芬前体; (3S,4R)-3-((苯并[D] [1,3]二氧杂环戊烯-5-基氧基)甲基)-4-(4-氟苯基)哌啶; 帕罗西汀-D6; 反-(-)-3-[(1,3-苯并二噁茂-5-基-氧)甲基]-4-(4-氟苯基)哌啶; 帕罗西汀碱; 氟苯哌苯醚; 乙腈中帕罗西汀; 帕罗西汀系统适应性 标准品; 帕罗西汀标准品; 帕罗西丁碱; 布洛芬钠前体; 帕罗西汀检测标准品; 帕罗西汀POXETINE; 帕罗西汀相关杂质; 无水盐酸帕罗西汀 标准品; (3S,4R)-3-[(苯并[d][1,3]二噁茂-5-基氧基)甲基]-4-(4-氟苯基)哌啶
• 英文别名: (3R)-3α-[3,4-(Methylenebisoxy)phenoxymethyl]-4β-(4-fluorophenyl)piperidine; Ibuprofen Precursor; Poxetine; BRL 29060A; rac trans-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine Hydrochloride; (3S-trans)-3-[(1,3-Benzodioxol-5-yl-oxy)methyl]-4-(4-fluorophenyl)piperidine; (3S,4R)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; aropax; POXETIN HCL; (-)-trans-4R-(4'-Fluorophenyl)-3S-((3',4'-methylenedioxyphenoxy)methyl)piperidine; Paroxetine (USP); Poxetine HCl anhydrous API; PoxetineHclBase; (3S,4R)-3-[(2H-1,3-benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)piperidine; 3α-(1,3-Benzodioxole-5-yloxymethyl)-4β-(4-fluorophenyl)piperidine; PARORETINE HCL; (-)-TRANS-4R-(4'-FLUOROPHENYL)-3S-[(3',4'-METHYLENEDIOXY-PHENOXY) METHYL]PIPERIDINE; (-)-trans-4-(4-Fluorophenyl)-3-(3,4-methylenedioxyphenoxymethyl)piperidine; Poxetine for system suitability CRS; (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)piperidine; Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, (3S,4R)- (9CI); (-)-trans-4-(4-Fluorophenyl)-3-hydroxy methyl-N-me; Ibuprofen Sodium Precursor; MFCD00869588; Poxetine //BP; Poxetine-002-3S4R; 3-(1,3-benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine hydrate hydrochloride; trans-(-)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; 3α-[(1,3-Benzodioxol-5-yl)oxymethyl]-4β-(4-fluorophenyl)piperidine; (-)-trans-4-(p-Fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]piperidine; OPAX 20; PAROXETIENE BASE; (-)-Paroxetine; FG 7051; POXETIENE BASE; Poxetine hydrochloride (anhydrous) CRS; (3S,4R)-3-[(1,3-BENZODIOXOL-5-YLOXY)METHYL]-4-(4-FFLUOROPHENYL)PIPERIDINE; Poxetine-002-SR; Paloxitene; (-)-Poxetine; 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-piperidin(3s-trans); PORETINE HCL; Poxetine Standd; (3S,4R)-3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-,(3s,4r)-piperidin; PAROXETIN HCL; Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, (3S-trans); PAXIL; AROPAX 20; trans-(-)-3-[(1，3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine; Piperidine,3-[(1,3-benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)-, (3S,4R); Paxil

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 451.7±45.0 °C at 760 mmHg
• 熔点: 114-116°C
• 分子式: C₁₉H₂₀FNO₃
• 分子量: 329.365
• 闪点: 227.0±28.7 °C
• 精确质量: 329.142731
• PSA: 39.72000
• LogP: 3.89
• 外观性状: 白色至灰白色粉末
• 蒸汽压: 0.0±1.1 mmHg at 25°C
• 折射率: 1.561
• 储存条件: 2-8℃，避光，惰性气体
• 稳定性:

  盐酸帕罗西汀(Paroxetine Hydroehloride)：C19H20FNO3.HCI。微小片状结晶，熔点118℃。; 盐酸帕罗西汀半水合物(Paroxetine Hydrochloride Hemihydrate)：C19H20FN03.HCI.1/2H2O。结晶，熔点129～131℃。; 马来酸帕罗西汀(Paroxetine Maleate)：C19H20FNO3.C4H4O4。从乙醇-乙醚结晶，熔点136～138℃。[α]_D-87°(C=5，乙醇)。急性毒性LD₅₀小鼠(mg/kg)：845皮下注射，500口服。

• 分子结构:

  1、 摩尔折射率：87.94

  2、 摩尔体积（cm³/mol）：271.5

  3、 等张比容（90.2K）：705.2

  4、 表面张力（dyne/cm）：45.5

  5、 极化率（10-24cm3）：34.86

• 计算化学:

  1.疏水参数计算参考值（XlogP）:3.5

  2.氢键供体数量:1

  3.氢键受体数量:5

  4.可旋转化学键数量:4

  5.互变异构体数量:无

  6.拓扑分子极性表面积39.7

  7.重原子数量:24

  8.表面电荷:0

  9.复杂度:402

  10.同位素原子数量:0

  11.确定原子立构中心数量:2

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: 帕罗西汀是一种苯基哌啶衍生物,是一种有效的选择性血清素再摄取抑制剂(SSRI)。帕罗西汀是一种非常弱的去甲肾上腺素(NE)摄取抑制剂,但在这个部位,它仍然比其他SSRIs更有效[1]。
• 相关类别:
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> 肾上腺素能受体
  研究领域 >> 神经疾病
  信号通路 >> 神经信号通路 >> 5-羟色胺转运蛋白
• 参考文献:

  [1]. M Bourin, et al. Paroxetine: a review. CNS Drug Rev. Spring 2001;7(1):25-47

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : TM4569200 CHEMICAL NAME : Piperidine, 3-((1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl )-, trans-(-)- CAS REGISTRY NUMBER : 61869-08-7 LAST UPDATED : 199801 DATA ITEMS CITED : 9 MOLECULAR FORMULA : C19-H20-F-N-O3 MOLECULAR WEIGHT : 329.40 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 400 ug/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - paresthesis REFERENCE : JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 58,175,1997 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 1400 ug/kg/7W-I TOXIC EFFECTS : Nutritional and Gross Metabolic - other changes REFERENCE : AJPSAO American Journal of Psychiatry. (American Psychiatric Assoc., Circulation Dept., 1400 K St., NW, Washington, DC 20005) V.78- 1921- Volume(issue)/page/year: 153,134,1996 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 4200 ug/kg/3W-I TOXIC EFFECTS : Endocrine - hyperglycemia REFERENCE : AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 125,782,1996 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 6700 ug/kg TOXIC EFFECTS : Behavioral - excitement REFERENCE : AJEMEN American Journal of Emergency Medicine. (WB Saunders, Philadelphia, PA) V.1- 1983- Volume(issue)/page/year: 11,682,1993 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 2800 ug/kg/7D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in sodium REFERENCE : MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 163,390,1995 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 946 mg/kg SEX/DURATION : female 1-22 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : ASSUA6 Acta Psychiatrica Scandinavica, Supplementum. (Munksgaard International Publishers, POB 2148, DK-1016 Copenhagen K, Denmark) No.160- 1961- Volume(issue)/page/year: 350,37,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 286 mg/kg SEX/DURATION : female 1-22 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) REFERENCE : ASSUA6 Acta Psychiatrica Scandinavica, Supplementum. (Munksgaard International Publishers, POB 2148, DK-1016 Copenhagen K, Denmark) No.160- 1961- Volume(issue)/page/year: 350,37,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 3150 mg/kg SEX/DURATION : male 9 week(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females) REFERENCE : ASSUA6 Acta Psychiatrica Scandinavica, Supplementum. (Munksgaard International Publishers, POB 2148, DK-1016 Copenhagen K, Denmark) No.160- 1961- Volume(issue)/page/year: 350,37,1989 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 700 mg/kg SEX/DURATION : female 2 week(s) pre-mating TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) REFERENCE : ASSUA6 Acta Psychiatrica Scandinavica, Supplementum. (Munksgaard International Publishers, POB 2148, DK-1016 Copenhagen K, Denmark) No.160- 1961- Volume(issue)/page/year: 350,37,1989

安全

• 危害码 (欧洲): Xi
• 危险品运输编码: 3249
• 包装等级: III
• 危险类别: 6.1(b)
• 海关编码: 2934999090

合成路线

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制备

方法1：化合物(I)和化合物(Ⅱ)在二环己基碳化二亚胺(DCC)存在下，缩合得到帕罗西汀。
方法2：化合物(I)转化为甲磺酸酯后，再和化合物(Ⅱ)的钠盐反应，得到帕罗西汀。
方法3：化合物(Ⅲ)或其它N-烷基取代的化合物溶于甲苯，在5℃，于15min中，加入氯甲酸(1-氯乙基)酯。加毕，搅拌18h。加入甲醇，再搅拌12h。移出溶剂，剩余物溶入热异丙醇，用活性炭和氧化铝处理，过滤。往滤液中加入水，再过滤收集析出的沉淀，即得盐酸帕罗西汀半水合物，收率92%。

海关

海关编码	2934999090
中文概述	2934999090. 其他杂环化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%