CAS: 93413-69-5; Venlafaxine

该化合物是一种处方药物,主要用作抗抑郁剂,被归类为血清内分泌肾上腺素再摄入抑制剂(SNRI),其化学配方为C17H27NO2,并具有苯乙胺结构,有助于其药理效应.Venlafaxine以其能够提高大脑血清素和无肾上腺素水平而著称,从而有助于缓解抑郁和焦虑症症状.该物质通常以延长释放胶囊或药片的形式施用,允许每天服用一次.Venlafaxine的特点是水中中溶性,有机溶剂中溶性较高,影响其吸收和生物利用率.常见副作用可能包括恶心,眩晕和增加血压,在治疗期间需要仔细监测.与许多药物一样,个人反应可以不同,病人必须咨询保健专业人员,以获得个性化咨询和管理.

英文名称Venlafaxine
中文名称文拉法辛
IUPAC名称1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol
其它别名[2-Dimethylamino-1-(4-methoxyphenyl)-ethyl]cyclohexan-1-ol
CAS编号93413-69-5
MFCD编号:MFCD00864385
EINECS号:618-944-2
FDA UNII编号:GRZ5RCB1QG
分子式:C17H27NO2
分子量:277.4
产品CID: 1973408
产品分类原料药 → 神经系统用药 → 抗抑郁、躁狂药

相似结构搜索
InChIKey: PNVNVHUZROJLTJ-UHFFFAOYNA-N
InChI=1/C17H27NO2/c1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h7-10,16,19H,4-6,11-13H2,1-3H3…
计算化学: 氢键受体数3.0氢键供体数1.0可旋转键数5.0

物理性质

熔点72-74 °C
沸点397.6±27.0 °C at 760 mmHg
闪点194.2±23.7 °C
密度1.1±0.1 g/cm3
pKa:pKa 9.5 (Uncertain)
PSA:32.7
LogP:2.91
折射率1.544
蒸汽压0.0±1.0 mmHg at 25°C
溶解性Soluble In Dichloromethane, Ethyl Acetate
外观形态白色至类白色结晶
储存条件请置于阴暗处, 惰性气氛中,2-8°C
产品应用文拉法辛(93413-69-5)的用途:该药能同时抑制5-羟色胺和去甲肾上腺素的回收.用于抗抑郁.

欧盟法规

REACH注册ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

合成目标产物 Venlafaxine 主要起始原料 Formaldehyde And Formic Acid And 2-(1-Hydroxycyclohexyl)-2-(4-Methoxyphenyl)Acetonitrile
93413-77-5 = 93413-69-5
反应条件:1.1 Solvents: Water; 10 Min,Rt1.2 Ph 7,Rt; 10 Min,Rt1.3 Rt; 10 Min,Rt; Rt -> 60 °C; 3 - 4 H,60 °C; 60 °C -> 100 °C; 95 - 100 °C; 100 °C -> 20 °C1.4 Reagents: Sodium Hydroxide Solvents: Water; Ph 10 - 13
标题:A Process For The Preparation Of Venlafaxine
参考文献:India]

99300-78-4 = 93413-69-5
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; > 1 Min,Rt
标题:Efficient Resolution Of Venlafaxine And Mechanism Study Via X-Ray Crystallography
作者:Liu,Zhi-Jin; Liu,Han; Chen,Xuan-Wen; Lin,Min; Hu,Yu; Et Al
参考文献:Chirality 日期:2018 卷标:30(3) 页码:268-274]

99300-78-4 = 93413-69-5
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dichloromethane,Water; 1 H,10 °C
标题:Preparation And Formulation Of O-Desmethyl Venlafaxine Enantiomers
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Formic Acid Solvents: Water; 20 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2,Rt1.3 Reagents: Sodium Hydroxide Solvents: Water; Basified,Cooled
标题:Preparation Of (-)-Venlafaxine And Derivatives As Neuronal Monoamine Reuptake Inhibitors.
参考文献:World Intellectual Property Organization]

1094598-37-4 = 93413-69-5
反应条件:1.1 Catalysts: Nickel Solvents: Water; 10 Min,60 °C1.2 Reagents: Sodium Borohydride; 15 - 20 Min,60 °C; 1.5 H,60 °C
标题:A Chemoselective Deoxygenation Of N-Oxides By Sodium Borohydride-Raney Nickel In Water
作者:Gowda,Narendra B.; Rao,Gopal Krishna; Ramakrishna,Ramesha A.
参考文献:Tetrahedron Letters 日期:2010 卷标:51(43) 页码:5690-5693]

1714141-74-8 = 93413-69-5
反应条件:1.1 Reagents: Magnesium Solvents: Tetrahydrofuran; Heated1.2 Catalysts: Cuprous Iodide; 15 Min1.3 Solvents: Tetrahydrofuran; -40 °C; 4 H,-40 °C1.4 Reagents: Ammonium Chloride Solvents: Water
标题:A Process For The Preparation Of Venlafaxine
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Formic Acid,Triethylamine Catalysts: Cobalt Oxide (Co3O4) (On Nitrogen Doped Graphene (Carbon)) Solvents: Tert-Butanol,Water; 14 H,100 °C
标题:Expedient Synthesis Of N-Methyl- And N-Alkylamines By Reductive Amination Using Reusable Cobalt Oxide Nanoparticles
作者:Senthamarai,Thirusangumurugan; Murugesan,Kathiravan; Natte,Kishore; Kalevaru,Narayana V.; Neumann,Helfried; Et Al
参考文献:Chemcatchem 日期:2018 卷标:10(6) 页码:1235-1240]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Hydrogen Catalysts: Cobalt Solvents: Tetrahydrofuran,Water; 24 H,40 Bar,120 °C
标题:Mof-Derived Cobalt Nanoparticles Catalyze A General Synthesis Of Amines
作者:Jagadeesh,Rajenahally V.; Murugesan,Kathiravan; Alshammari,Ahmad S.; Neumann,Helfried; Pohl,Marga-Martina; Et Al
参考文献:Science (Washington 日期:2017 卷标:358(6361) 页码:326-332]

= 93413-69-5
反应条件:1.1 Reagents: Potassium Borohydride Solvents: Methanol; Rt -> 0 °C; 0 - 5 °C; 5 °C -> Rt; 3 - 4 H,Rt1.2 Reagents: Sodium Hydroxide Solvents: Water
标题:Preparation Of Venlafaxine From 4-Methoxyphenylacetonitrile
参考文献:China]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Formic Acid Solvents: Water; Rt -> 98 °C; 20 H,98 °C; 98 °C -> 10 °C1.2 Reagents: Sodium Hydroxide Solvents: Ethyl Acetate,Water; Ph 71.3 Reagents: Ammonium Hydroxide Solvents: Water; Ph 10 - 10.51.4 Reagents: Hydrochloric Acid Solvents: Isopropanol; Ph 1 - 1.5,30 °C; 30 °C -> 60 °C; 60 - 90 Min,60 °C; 60 °C -> 10 °C; 60 Min,10 °C
标题:A Process For The Preparation Of Venlafaxine And Intermediates Thereof
参考文献:India]

93413-77-5 = 93413-69-5
反应条件:1.1 Solvents: Water
标题:2-Phenyl-2-(1-Hydroxycycloalkyl)Ethylamine Derivatives: Synthesis And Antidepressant Activity
作者:Yardley,John P.; Husbands,G. E. Morris; Stack,Gary; Butch,Jacqueline; Bicksler,James; Et Al
参考文献:Journal Of Medicinal Chemistry 日期:1990 卷标:33(10) 页码:2899-905]

99300-78-4 = 93413-69-5
反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Dichloromethane,Water; 1 H,10 °C
标题:Preparation And Pharmaceutical Formulation Of Enantiomers Of O-Desmethyl Venlafaxine
参考文献:United States]

93413-76-4 = 93413-69-5
反应条件:1.1 Reagents: Acetic Acid Catalysts: Palladium Solvents: Water; 30 Min,Rt -> 5 °C1.2 Reagents: Hydrogen; 3.5 H,12 Bar,5 - 15 °C1.3 15 °C -> 60 °C; 30 - 35 °C
标题:Preparation Of Venlafaxine And Its Derivatives By In Situ Or One-Pot Method For Hydrogenation Of Nitriles And Reductive Amination Of Formaldehyde And Its Equivalents
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Formic Acid Solvents: Water; 20 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2,Rt1.3 Reagents: Sodium Hydroxide Solvents: Water; Basified,Cooled
标题:Preparation Of Derivatives Of Venlafaxine And Their Inhibition Of Neuronal Monoamine Reuptake
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Formic Acid Solvents: Water; 20 H,Reflux; Reflux -> Rt1.2 Reagents: Hydrochloric Acid Solvents: Water; Ph 2,Rt1.3 Reagents: Sodium Hydroxide Solvents: Water; Basified,Cooled
标题:Preparation Of Derivatives Of (+)-Venlafaxine As Inhibitors Of Neuronal Monoamine Reuptake.
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Sodium Hydroxide Catalysts: Alumina (10 Wt% Cu And 5 Wt% Co) Solvents: Methanol; 4 H,190 °C
标题:Tunable Mono- And Di-Methylation Of Amines With Methanol Over Bimetallic Cuco Nanoparticle Catalysts
作者:Li,Ke-Ming; Zhang,Qi; Xu,Zhong-Ming; Chen,Ran; Liu,Tian-Tian; Et Al
参考文献:Green Chemistry 日期:2022 卷标:24(15) 页码:5965-5977]

93413-77-5 = 93413-69-5
反应条件:1.1 Catalysts: Vitride Solvents: Tetrahydrofuran; 0 °C; 6 H,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; 0 °C
标题:Method Of Preparation Venlafaxine And Its Salts As Antidepressant
参考文献:China]

93413-77-5 = 93413-69-5
反应条件:1.1 Solvents: 1,4-Dioxane,Water; 5 Min,Rt; Rt; 90 - 92 °C
标题:Process For Preparation Of Venlafaxine And Intermediates
参考文献:World Intellectual Property Organization]

93413-77-5 = 93413-69-5
反应条件:1.1 Reagents: Sodium Carbonate Catalysts: Iron Solvents: Dimethyl Sulfoxide,Water; 24 H,130 °C
标题:Convenient Iron-Catalyzed Reductive Aminations Without Hydrogen For Selective Synthesis Of N-Methylamines
作者:Natte,Kishore; Neumann,Helfried; Jagadeesh,Rajenahally V.; Beller,Matthias
参考文献:Nature Communications 日期:2017 卷标:8(1) 页码:1-9]

295366-48-2 = 93413-69-5
反应条件:1.1 Reagents: Sodium Borohydride Solvents: Tetrahydrofuran; 30 Min,Rt1.2 Reagents: Chlorotrimethylsilane; Rt; 3 H,Reflux1.3 Reagents: Acetic Acid Solvents: Water
标题:Process For Preparation Of Venlafaxine Hydrochloride For Use In Medicine Field
参考文献:China

盐酸文拉法辛置于sodium Hydroxide体系中,用水作为反应溶剂,以98.9%的收率获得产物文拉法辛
参考文献:文拉法辛的有效拆分和通过x射线晶体学的机理研究.
标题:文拉法辛的有效拆分和通过x射线晶体学的机理研究.
摘要:研究了许多解决因素,以提高文拉法辛1的分离度.使用类似的"荷兰拆分"方法从酒石酸衍生物中筛选出一种有效的拆分剂,O,O'-二对甲苯甲酰(r,R)-酒石酸2.当rac-1和2的比例在thf中,水很少时(10:1 V / V)时,分离效率高达88.4%.对映体纯的文拉法辛制备成具有99.1%ee的产率和82.2%的收率.首先通过x射线晶体学研究解释了手性拆分机理.一种具有非常好溶解性的非对映异构盐形成酸性的盐(R)-1 . 2的圆柱状超分子结构而另一种溶解度较低的非对映异构盐则通过对映体自组装形成中性盐2(S)-1 . 2形成多层夹心超分子结构.如非对映异构体盐的特殊结构所示,水分子在光学拆分中起关键作用.
DOI:10.1002/chir.22790

海关参考信息

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2902700000-异丙基苯
2905122000-异丙醇
2905143000-叔丁醇
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专利信息

专利号:US-9527800-B2
优先权日:2013-10-29
标题:Process for total synthesis of venlafaxine
发明人：CHAVAN SUBHASH PRATAPRAO; PAWAR KAILASH PRALHAD
权利人:COUNCIL SCIENT IND RES
摘要:There is a need for short, resolution free asymmetric process for synthesis of one isomer of venlafaxine, (âˆ’)-venlafaxine. The invention provides a novel, short process of synthesis of (âˆ’)-venlafaxine, with yield greater than 50% and ee>99%. This process can be used for racemic synthesis of venlafaxine with overall yield 65%.

专利号:US-7612210-B2
优先权日:2005-12-05
标题:Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols
发明人：MAHANEY PAIGE ERIN; ANTANE MADELENE MIYOKO; SUN JERRY SHUNNENG
权利人:WYETH CORP
摘要:A process for the enantioselective synthesis of an (S)- or (R)-1-[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol and analogues or salt thereof are described. The method involves the steps of (a) reacting an (S) or (R) 4-benzyloxazolidinone with a mixed anhydride of a methyoxyphenylacetic acid under conditions which form a oxazolidinone, (4S)- or (4R)-4-benzyl-3-[methyoxyphenyl]acetyl]-oxazolidin-2-one, (b) treating the (4S)- or (4R)-4-benzyl-3-[(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one with an aprotic amine base and titanium chloride in a chlorinated solvent under conditions which permit formation of the corresponding anion, (c) mixing the corresponding anion with titanium chloride and cylcohexanone under conditions which permit an aldol reaction to form the corresponding (4S)- or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one,(d) hydrolyzing the (4S)â€” or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one to form a chiral acid (2S or 2R)-(1-hydroxycyclohexyl)-methoxyphenyl)acetic acid, (e) coupling the chiral phenylacid to a secondary amine to form an amide, and (f) reducing the amide to form an (S) or (R) 1[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol or a salt thereof.

专利号:US-2003083352-A1
优先权日:2000-07-31
标题 :Synthesis of imidazole intermediates
发明人：HELAL CHRISTOPHER J
权利人:PFIZER
摘要:The invention provides a method for synthesis of compounds of formula n n n wherein R 1 and R 19 are as defined. Compounds of formula 12 are useful as intermediates for synthesizing compounds having pharmacological activity inhibiting cdk5, cdk2, and GSK-3.

专利号:US-10005720-B2
优先权日:2013-04-05
标题:Compounds useful for the treatment of metabolic disorders and synthesis of the same
发明人：SEXTON JONATHAN Z; BRENMAN JAY E; MUSSO DAVID L
权利人:NORTH CAROLINA CENTRAL UNIV; UNIV NORTH CAROLINA CHAPEL HILL
摘要:The present invention provides compounds of Formula (I): wherein variables X, Y, Z and R1 are as described herein. Some of the compounds described herein are glutamate dehydrogenase activators. The invention is also directed to pharmaceutical compositions comprising these compounds, uses of these compounds and compositions in the treatment of metabolic disorders as well as synthesis of the compounds.

专利号:US-2006030625-A1
优先权日:2004-08-06
标题 :Dietary neurotransmitter precursors for balanced synthesis of neurotransmitters
发明人：HART CHERYLE RAM; GROSSMAN RONALD S; RAM HERBERT
权利人:HART CHERYLE RAM; GROSSMAN RONALD S; RAM HERBERT
摘要:Dietary supplements for treating a neurotransmitter deficiency include one or more precursors of the deficient neurotransmitter and a cofactor for activating in vivo enzymatic synthesis of the deficient neurotransmitter. The dietary supplements can also include an appropriate neurotransmitter, such as an amino acid. When administered through the oral mucosa, increases in levels of the deficient neurotransmitters and relief from deficiency symptoms are obtained.

专利号:US-9409855-B2
优先权日:2012-07-25
标题 :Asymmetric synthesis of (âˆ’)-venlafaxine using organocatalyst
发明人：CHAVAN SUBHASH PRATAPRAO; GARAI SUMANTA; PAWAR KAILASH PRALHAD
权利人:COUNCIL SCIENT IND RES
摘要:The patent discloses an asymmetric synthesis of (âˆ’)-venlafaxine using an organocatalyst via a unified strategy employing organcatalytic Michael addition, regio-selective dehydration and selective epoxide ring opening.

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合成参考文献

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参考文献:10.1186/1744-859x-9-3|10.1186/1744-859x-9-s1-s226
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参考文献:10.1016/j.encep.2009.02.004
摘要:Amara G, Saada W, Ben Nasr S, Ben Hadj Ali B. [Cholinesterase inhibitors and depression in the elderly]. Encephale. 2010 Feb;36(1):77–81. doi: 10.1016/j.encep.2009.02.004.
参考文献:10.1016/j.ajem.2009.05.010
摘要:Charniot J, Vignat N, Monsuez J, Kidouche R, Avramova B, Artigou J, Albertini J. Cardiogenic shock associated with reversible dilated cardiomyopathy during therapy with regular doses of venlafaxine. The American Journal of Emergency Medicine. 2010 Feb;28(2):256.e1–5. doi: 10.1016/j.ajem.2009.05.010.
参考文献:10.1155/2011/893905
摘要:Ishizaki J, Mimura M. Dysthymia and Apathy: Diagnosis and Treatment. Depression Research and Treatment. 2011;2011():1–7. doi: 10.1155/2011/893905.