萘替芬 | 65472-88-0

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 抗真菌类药
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘替芬
• 中文别名: N-反-肉桂基-N-甲基-(1-萘甲基)胺盐酸盐；(E)-N-甲基-N-(3-苯基-2-丙烯基)-1-萘甲胺；桂萘甲胺；萘夫替芬；3-苯基-2-丙烯-N-甲基-1-萘甲胺；盐酸萘替芬
• 英文名称: naftifine
• 英文别名: (E)-N-methyl-N-(naphthalen-1-ylmethyl)-3-phenylprop-2-en-1-amine；trans-n-cinnamyl-n-methyl-(1-naphthylmethyl)amine
• CAS: 65472-88-0
• 化学式: C₂₁H₂₁N
• 分子量: 287.404
• InChiKey: OZGNYLLQHRPOBR-DHZHZOJOSA-N

物化性质

• 熔点：
  177 °C
• 沸点：
  bp0.015 torr 162-167°
• 密度：
  1.082±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（少量溶解）、DMSO（少量溶解）、乙酸乙酯（少量溶解）、甲醇（极少量）
• 稳定性/保质期：
  远离氧化物、高温和强光。

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

ADMET

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用概述：外用萘替芬在哺乳期尚未进行研究。由于局部应用后只有4%到6%被吸收，因此认为对哺乳婴儿的风险较低。[1] 避免涂抹在乳头区域，并确保婴儿的皮肤不直接接触已治疗的皮肤区域。只有水溶性乳膏、凝胶或液体产品可以涂抹在乳房上，因为软膏可能会使婴儿通过舔食接触到高水平的矿物石蜡。[2] ◉ 对哺乳婴儿的影响：截至修订日期，没有找到相关的已发布信息。 ◉ 对泌乳和母乳的影响：截至修订日期，没有找到相关的已发布信息。

◉ Summary of Use during Lactation:Topical naftifine has not been studied during breastfeeding. Because only 4 to 6% is absorbed after topical application, it is considered a low risk to the nursing infant.[1] Avoid application to the nipple area and ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only water-miscible cream, gel or liquid products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.[2] ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information was not found as of the revision date.

来源:Drugs and Lactation Database (LactMed)

安全信息

• 海关编码：
  2921499090
• 危险品标志：
  Xn,Xi
• 安全说明：
  S22,S24/25,S26
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• RTECS号：
  DB7350000
• 储存条件：
  存放在密封容器内，并置于阴凉、干燥处。请确保储存位置远离氧化剂、火源及高温环境。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine
Hydrochloride
Portland OR
Synonym Not available.
C21H21N•HCl
Chemical Formula
CAS Number 65472-88-0

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Section II. Composition and Information on Ingredients
Chemical Name CAS Number Percent (%) TLV/PEL Toxicology Data
N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine 65472-88-0 Min. 98.0 (T) Not available. Not available.
Hydrochloride

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Section III. Hazards Identification
Acute Health Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is
not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. DO NOT use an eye ointment. Flush eyes with running water for a minimum
of 15 minutes, occasionally lifting the upper and lower eyelids. Seek medical attention. Treat symptomatically and
supportively.
Skin Contact If the chemical gets spilled on a clothed portion of the body, remove the contaminated clothes as quickly as possible,
protecting your own hands and body. Place the victim under a deluge shower. If the chemical touches the victim's
exposed skin, such as the hands: Gently and thoroughly wash the contaminated skin with running water and non-abrasive
soap. Be particularly careful to clean folds, crevices, creases and groin. Cover the irritated skin with an emollient. Seek
medical attention. Treat symptomatically and supportively. Wash any contaminated clothing before reusing.
Inhalation If the victim is not breathing, perform artificial respiration. Loosen tight clothing such as a collar, tie, belt or waistband. If
breathing is difficult, oxygen can be administered. Seek medical attention. Treat symptomatically and supportively.
Ingestion INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Loosen tight clothing such as a collar, tie, belt, or waistband. If the victim is not breathing, administer artificial respiration.
Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic material
was ingested; the absence of such signs, however, is not conclusive. Seek immediate medical attention and, if possible,
show the chemical label. Treat symptomatically and supportively.

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Section V. Fire and Explosion Data
Auto-Ignition Not available.
Flammability Combustible.
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO 2), nitrogen oxides (NO, NO2), halogenated compounds.
WARNING: Highly toxic HCl gas is produced during combustion.
Fire Hazards
No specific information is available regarding the flammability of this compound in the presence of various materials.
Explosion Hazards Risks of explosion of the product in presence of mechanical impact: Not available.
Risks of explosion of the product in presence of static discharge: Not available.
No additional information is available regarding the risks of explosion.
Continued on Next Page
N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine
Hydrochloride
Fire Fighting Media
SMALL FIRE: Use DRY chemicals, CO 2, water spray or foam.
and Instructions LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.

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Section VI. Accidental Release Measures
Spill Cleanup In case of a spill and/or a leak, always shut off any sources of ignition, ventilate the area, and exercise caution. Use a
shovel to put the material into a convenient waste disposal container. Finish cleaning the spill by rinsing any
Instructions
contaminated surfaces with copious amounts of water. Consult federal, state, and/or local authorities for assistance on
disposal.

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Section VII. Handling and Storage
Handling and Storage Keep away from heat and sources of ignition. Mechanical exhaust required. When not in use, tightly seal the container
and store in a dry, cool place. Avoid excessive heat and light. DO NOT breathe dust. In case of insufficient ventilation,
Information
wear suitable respiratory equipment. If you feel unwell, seek medical attention and show the label when possible. Treat
symptomatically and supportively. Avoid contact with skin and eyes.
Always store away from incompatible compounds such as oxidizing agents.

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Section VIII. Exposure Controls/Personal Protection
Engineering Controls Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below
recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to
airborne contaminants below the exposure limit.
Personal Protection Splash goggles. Lab coat. Dust respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling
this product.
Exposure Limits
Not available.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C Powder. Solubility
Not available.
Not available.
Specific Gravity
Molecular Weight Partition Coefficient
323.87 Not available.
Boiling Point Vapor Pressure
Not available. Not available.
Melting Point 177°C (350.6°F) Vapor Density Not available.
Refractive Index Not available. Volatility Not available.
Critical Temperature Not available. Odor Not available.
Viscosity Not available. Taste Not available.

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents.

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Section XI. Toxicological Information
RTECS Number Not available.
Eye contact. Inhalation. Ingestion.
Routes of Exposure
Toxicity Data Not available.
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
There is no known effect from chronic exposure to this product. Repeated or prolonged exposure to this compound is not
known to aggravate existing medical conditions.
Acute Toxic Effects No specific information is available in our data base regarding the toxic effects of this material for humans. However,
exposure to any chemical should be kept to a minimum. Skin and eye contact may result in irritation. May be harmful if
inhaled or ingested. Always follow safe industrial hygiene practices and wear proper protective equipment when handling
this compound.
Continued on Next Page
N-trans-Cinnamyl-N-methyl-(1-naphthylmethyl)amine
Hydrochloride

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Section XII. Ecological Information
Ecotoxicity Not available.
Environmental Fate Not available.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local or regional authorities. You may be able to dissolve or mix material with
Waste Disposal
a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state, and local regulations when disposing of this substance.

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Section XIV. Transport Information
DOT Classification Not a DOT controlled material (United States).
PIN Number Not applicable.
Proper Shipping Name
Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not controlled under WHMIS (Canada).
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements Not available.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
无色粘稠液体，沸点为162～167℃（2.00Pa）。盐酸萘替芬（Naftifine Hydrochloride）：C₂₁H₂₁N:HCl。[65473-14-5]。在丙醇中结晶，熔点177℃。

用途
广谱局部抗真菌药，主要用于皮肤真菌的治疗。其疗效优于发癣退、克霉唑、美康唑和益康唑等药物，并且毒性较低。

生产方法
方法一：将1.42g 1-甲基-1-萘甲胺盐酸盐与2.89g碳酸钠溶于10ml二甲基甲酰胺中，室温下滴加1.25g肉桂基氯。反应完毕后，在室温继续搅拌18小时。过滤并减压浓缩滤液，剩余物溶解在甲苯中，用无水硫酸钠干燥，再进行浓缩和减压蒸馏，最终获得萘替芬，其沸点为162～167℃/2.00Pa。将萘替芬与含氯化氢的异丙醇溶液反应，可结晶得到盐酸萘替芬，熔点为177℃（丙醇重结晶）。也可通过异丙醇-乙醚重结晶获得。

另一种方法：以1-氯甲基萘为原料，在5～7℃下向其乙醇溶液中滴加30%甲胺乙醇溶液。反应完成后在室温下搅拌过夜，蒸除乙醇，剩余物溶于氯仿，洗涤至中性并干燥后浓缩。减压蒸馏收集133～134℃/0.533kPa的馏分即为N-甲基-1-萘甲胺，收率为70%。将浓盐酸加入到N-甲基-1-萘胺中，并添加碳酸钠和二甲基甲酰胺，滴加肉桂基氯后搅拌并过滤。浓缩滤液至干，加入甲苯干燥并浓缩，再加入异丙醇调节pH值为3。通过乙醚进行洗涤、过滤并干燥，可获得白色固体的盐酸萘替芬，收率为59.3%，熔点175～177℃。

方法二：在冰浴冷却下，向30%甲胺的乙醇溶液中滴加1-氯甲基萘的无水乙醇溶液，并于室温放置过夜以获得N-甲基-1-萘甲胺。将该化合物溶解在乙醇中，加入浓盐酸、35%甲醛水溶液和苯乙酮，在加热回流并补加聚甲醛细粉的情况下进行Mannich反应得到2-[N-甲基-N-(1-萘甲基)氨基]乙基苯基酮。在催化量的相转移催化剂存在下，于乙酸乙酯中使用硼氢化钠将羰基还原为羟基。最后，在盐酸中回流脱水以制得萘替芬的盐酸盐，总收率为30.1%。

反应信息

• 作为反应物：
  描述：

  萘替芬 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以78%的产率得到3-[methyl(naphthalen-1-ylmethyl)amino]-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  ADENYLYL CYCLASE INHIBITORS FOR NEUROPATHIC AND INFLAMMATORY PAIN

  摘要：

  这项发明通常涉及腺苷酸环化酶抑制剂化合物及利用这些化合物治疗神经病理性或炎症性疼痛的方法。

  公开号：

  US20160272572A1
• 作为产物：
  描述：

  N-cinnamyl-N-methyl-1-naphthylamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以89%的产率得到萘替芬
  参考文献：
  名称：

  一种胺类化合物及其制备方法与应用

  摘要：

  本发明公开了一种含有烯丙基或苄基的胺类化合物及其制备方法与应用。本发明通过将原料1、胺、催化剂、添加剂依次加入到反应溶剂中，在空气氛围和50～120℃条件下搅拌反应12～24h，得到反应液；其中，所述原料1为烯丙醇或苄醇；所述原料1、胺、催化剂、添加剂和反应溶剂的摩尔体积比为(0.2～8)mmol：(0.4～12)mmol：(0.01～0.4)mmol：(0.01～0.4)mmol：(2～40)mL；除去所述反应液的反应溶剂，再通过薄层层析法/柱层析法纯化，展开剂体系为石油醚/乙酸乙酯，得到含有烯丙基或苄基的胺类化合物。该胺类化合物可应用在生物和药物活性分子的骨架的制备中。本发明制备方法适用的底物范围广泛，操作方便，绿色环保。

  公开号：

  CN113277963B

文献信息

• [EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
  申请人：GILEAD APOLLO LLC

  公开号：WO2017075056A1

  公开（公告）日：2017-05-04

  The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.

  本发明提供了化合物I和II，这些化合物可用作乙酰辅酶A羧化酶（ACC）的抑制剂，以及它们的组合物和使用方法。
• THIENYLPYRIDYLCARBOXAMIDES
  申请人：Dunkel Ralf

  公开号：US20110105564A1

  公开（公告）日：2011-05-05

  Novel thienylpyridylcarboxamides of the formula (I) The present application is also directed to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and also novel intermediates and their preparation.

  新型噻吩基吡啶基羧酰胺的化学式（I） 本申请还涉及多种制备这些化合物的方法，以及它们用于控制不受欢迎的微生物的用途，还有新颖的中间体及其制备。
• PYRIMIDINYL AND 1,3,5-TRIAZINYL BENZIMIDAZOLES AND THEIR USE IN CANCER THERAPY
  申请人：Rewcastle Gordon William

  公开号：US20110009405A1

  公开（公告）日：2011-01-13

  Provided herein are pyrimidinyl and 1,3,5-triazinyl benzimidazoles of Formula I, and their pharmaceutical compositions, preparation, and use as agents or drugs for cancer therapy, either alone or in combination with radiation and/or other anticancer drugs.

  本文提供了式I的嘧啶基和1,3,5-三嗪基苯并咪唑化合物，以及它们的药物组合物、制备方法，以及作为抗癌治疗药物或药剂的用途，可以单独使用，也可以与放疗和/或其他抗癌药物联合使用。
• N-ARYLAMIDINE-SUBSTITUTED TRIFLUOROETHYL SULFIDE DERIVATIVES AS ACARICIDES AND INSECTICIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20140315898A1

  公开（公告）日：2014-10-23

  The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I) in which X 1 , X 2 , X 3 , X 4 , R 1 , R 2 , R 3 , n have the meanings given in the description—to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation

  本发明涉及公式（I）中的新型N-芳酰胺取代三氟乙基硫醚衍生物，其中X1、X2、X3、X4、R1、R2、R3、n的含义如描述所示—它们作为杀螨剂和杀虫剂用于控制动物害虫，并涉及其制备的过程和中间体。
• FUNGICIDAL ISOXAZOLIDINES
  申请人：TSENG CHI-PING

  公开号：US20090270407A1

  公开（公告）日：2009-10-29

  Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein A, B, D, R 1 , R 2 , R 3 , X and m are as defined in the disclosure. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

  公开的是Formula 1的化合物，包括所有的几何和立体异构体、N-氧化物和盐， 其中 A、B、D、R 1 、R 2 、R 3 、X和m如披露中所定义。 还公开了含有Formula 1化合物的组合物，以及用于控制由真菌病原体引起的植物疾病的方法，包括施用本发明的化合物或组合物的有效量。