50-60-2

• 常用中文名：酚妥拉明
• 常用英文名：Phentolamine
• CAS号：50-60-2
• 分子式：C₁₇H₁₉N₃O
• 分子量：281.352
• 相关类别： 原料药 循环系统用药 周围血管扩张药
• 发布时间：2018-08-19 22:12:15
• 更新时间：2024-01-03 08:07:26
• 酚妥拉明是一种有效、选择性和口服活性的α1肾上腺素能和α2肾上腺素能受体拮抗剂。酚妥拉明可用于治疗勃起功能障碍[1][2][3]。

名称

• 中文名: 酚妥拉明
• 英文名: phentolamine
• 中文别名: 3-[[(4,5-二氢-1H-咪唑-2-基)甲基](4-甲苯基)氨基]苯酚
• 英文别名: Fentolamin; EINECS 200-053-1; MFCD00242985; Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphenyl)amino)-; 2-(N-[m-Hydroxyphenyl]-p-toluidinomethyl)imidazoline; Phenol, 3-[[(4,5-dihydro-1H-imidazol-2-yl)methyl](4-methylphenyl)amino]-; Phentalamine; Regitin; Phenotolamine; 3-[(4,5-Dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol; Dibasin; Fentolamina; Regitine; Phentolaminum; Phentolamine; 3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol; Rogitine

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 551.0±45.0 °C at 760 mmHg
• 熔点: 177 - 178ºC
• 分子式: C₁₇H₁₉N₃O
• 分子量: 281.352
• 闪点: 287.0±28.7 °C
• 精确质量: 281.152802
• PSA: 47.86000
• LogP: 3.60
• 外观性状: 白色结晶粉末
• 蒸汽压: 0.0±1.5 mmHg at 25°C
• 折射率: 1.626
• 储存条件: -20°C
• 计算化学:

  1.疏水参数计算参考值（XlogP）:2.6

  2.氢键供体数量:2

  3.氢键受体数量:3

  4.可旋转化学键数量:4

  5.互变异构体数量:3

  6.拓扑分子极性表面积47.9

  7.重原子数量:21

  8.表面电荷:0

  9.复杂度:363

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  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: 酚妥拉明是一种有效、选择性和口服活性的α1肾上腺素能和α2肾上腺素能受体拮抗剂。酚妥拉明可用于治疗勃起功能障碍[1][2][3]。
• 相关类别:
  研究领域 >> 内分泌
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> 肾上腺素能受体
• 体内研究: 酚妥拉明(5-20mg/kg；i.p.)有效抑制士的宁(2mg/kg,i.p.),并减弱DOP(4mg/kg,i.p.)对小鼠的惊厥增强作用[2]。酚妥拉明(1mg/kg；i.p.)通过抑制小鼠b细胞a2A肾上腺素受体增加胰岛素分泌[3]。动物模型：WT小鼠[3]剂量：1mg/kg给药：IP结果：血糖降低,胰岛素水平升高。
• 参考文献:

  [1]. Goldstein I I. Oral phentolamine: an alpha-1, alpha-2 adrenergic antagonist for the treatment of erectile dysfunction. Int J Impot Res. 2000 Mar;12(S1):S75-S80

  [2]. Amabeoku G, et al. Strychnine-induced seizures in mice: the role of noradrenaline. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jul;18(4):753-63.

  [3]. Fagerholm V, et al. alpha2A-adrenoceptor antagonism increases insulin secretion and synergistically augments the insulinotropic effect of glibenclamide in mice. Br J Pharmacol. 2008 Jul;154(6):1287-96.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : SL0700000 CHEMICAL NAME : Phenol, 3-(((4,5-dihydro-1H-imidazol-2-yl)methyl)(4-methylphe nyl)amino)- CAS REGISTRY NUMBER : 50-60-2 BEILSTEIN REFERENCE NO. : 0272944 LAST UPDATED : 199612 DATA ITEMS CITED : 7 MOLECULAR FORMULA : C17-H19-N3-O MOLECULAR WEIGHT : 281.39 WISWESSER LINE NOTATION : T5M CN BUTJ B1NR CQ&R D1 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1 gm/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: 112,319,1957 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 200 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - ptosis Behavioral - tremor Behavioral - ataxia REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 21,1727,1971 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 35 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: 105,317,1956 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 2 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada) TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 200 mg/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - convulsions or effect on seizure threshold REFERENCE : SMWOAS Schweizerische Medizinische Wochenschrift. (Schwabe & Co., Steintorst 13, 4010 Basel, Switzerland) V.50- 1920- Volume(issue)/page/year: 81,352,1951 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 28 mg/kg TOXIC EFFECTS : Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - respiratory depression 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: 174,243,1968 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 100 ug/kg SEX/DURATION : female 8 day(s) after conception TOXIC EFFECTS : Reproductive - Maternal Effects - uterus, cervix, vagina REFERENCE : DPTHDL Developmental Pharmacology and Therapeutics. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 7(Suppl 1),72,1984

安全

• 安全声明 (欧洲): S26-S36/37/39-S45-S8-S25
• 危险品运输编码: UN 3264 8/PG 2
• WGK德国: 3
• 包装等级: II
• 危险类别: 8
• 海关编码: 2933290090

合成路线

61537-49-3 13338-49-3 ~% 50-60-2

文献：CIBA Patent: DE842062 , 1948 ; DRP/DRBP Org.Chem. Full Text Show Details CIBA Patent: US2503059 , 1948 ; Full Text Show Details Urech et al. Helvetica Chimica Acta, 1950 , vol. 33, p. 1386,1403

107-15-3 ~% 50-60-2

文献：CIBA Patent: DE842062 , 1948 ; DRP/DRBP Org.Chem. Full Text Show Details CIBA Patent: US2503059 , 1948 ;

上下游产品

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海关

海关编码	2933290090
中文概述	2933290090. 其他结构含非稠合咪唑环的化合物. 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, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933290090. other compounds containing an unfused imidazole ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%