消旋肾上腺素 | 329-65-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酚类
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 消旋肾上腺素
• 中文别名: 1-(3,4-二羟基苯基)-2-(甲基氨基)乙醇；DL-肾上腺素；(±)肾上腺素；3,4-二羟基-Α-(甲基氨基)苯甲醇；肾上腺素
• 英文名称: L-adrenaline
• 英文别名: L-epinephrine；2-hydroxy-4-[1-hydroxy-2-(methylazaniumyl)ethyl]phenolate
• CAS: 329-65-7
• 化学式: C₉H₁₃NO₃
• mdl: MFCD00063027
• 分子量: 183.207
• InChiKey: UCTWMZQNUQWSLP-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C (dec.)(lit.)
• 比旋光度：
  -0.5～+0.5°(D/20)(c=1,0.1mol/l HCl)
• 沸点：
  316.88°C (rough estimate)
• 密度：
  1.1967 (rough estimate)
• 溶解度：
  0.1 M HCL：2.5 mg/mL（13.65 mM；超声并用 HCl 将 pH 调节至 1）DMSO：1 mg/mL（5.46 mM；超声并用 HCl 将 pH 调节至 7）乙醇：< 1 mg/mL（不溶） H2O：< 0.1 mg/mL（不溶）
• 物理描述：
  3,4-dihydroxyl-alpha-[methylamino]methylbenzyl alcohol appears as odorless light brown or nearly white crystals. (NTP, 1992)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

ADMET

代谢

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

毒理性

• 在妊娠和哺乳期间的影响

◉ 母乳喂养期间使用总结：目前没有关于在哺乳期间使用肾上腺素的信息。由于肾上腺素的口服生物利用度差和半衰期短，乳汁中的肾上腺素不太可能影响婴儿。高剂量的静脉注射肾上腺素可能会减少乳汁产量或乳汁排放。低剂量的肌肉注射（如Epi-Pen）、硬脊膜外、局部、吸入或眼用肾上腺素不太可能干扰哺乳。为了在使用眼药水后显著减少药物的效果，可以在眼角处按压泪囊1分钟或更长时间，然后用吸水纸巾去除多余的溶液。肾上腺素是治疗过敏性休克的首选一线药物；在哺乳和非哺乳患者中应以相同的方式使用。 ◉ 对哺乳婴儿的影响：截至修订日期，未找到相关已发表信息。 ◉ 对泌乳和乳汁的影响：截至修订日期，未在哺乳母亲中找到相关已发表信息。在非哺乳对象和患有高催乳素血症的妇女中，静脉输注肾上腺素会降低血清催乳素浓度。动物数据显示，动脉内注射肾上腺素可以降低血清催乳素并抑制乳汁排放。然而，作为硬脊膜外镇痛一部分的低剂量肾上腺素输注并不会影响哺乳母亲的哺乳。已建立泌乳的母亲体内的催乳素水平可能不会影响她的哺乳能力。 一项埃及研究比较了75名接受2%利多卡因（n = 75）和70名接受2%利多卡因加1:200,000肾上腺素（n = 70）作为剖宫产后伤口浸润的效果。接受肾上腺素与利多卡因联合使用的患者术后89分钟开始哺乳，而仅接受利多卡因的患者为132分钟。这个差异在统计学上是显著的。

◉ Summary of Use during Lactation:No information is available on the use of epinephrine during breastfeeding. Because of its poor oral bioavailability and short half-life, any epinephrine in milk is unlikely to affect the infant. High intravenous doses of epinephrine might reduce milk production or milk letdown. Low-dose intramuscular (such as Epi-Pen), epidural, topical, inhaled or ophthalmic epinephrine are unlikely to interfere with breastfeeding. To substantially diminish the effect of the drug after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue. Epinephrine is the first line-medication of choice for treatment of anaphylaxis; it should be used in the same manner in breastfeeding and non-breastfeeding patients. ◉ Effects in Breastfed Infants:Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk:Relevant published information in nursing mothers was not found as of the revision date. Intravenous epinephrine infusion in nonnursing subjects and in women with hyperprolactinemia decreases serum prolactin concentrations. Animal data indicate that intraarterial epinephrine can decrease serum oxytocin and inhibit milk ejection. However, low-dose infusion of epinephrine as part of epidural analgesia does not impair breastfeeding in nursing mothers. The prolactin level in a mother with established lactation may not affect her ability to breastfeed. An Egyptian study compared lidocaine 2% (n = 75) to lidocaine 2% plus epinephrine 1:200,000 (n = 70) as a wound infiltration following cesarean section. Patients who received epinephrine in combination with lidocaine began breastfeeding at 89 minutes following surgery compared to 132 minutes for those receiving lidocaine alone. The difference was statistically significant.

来源:Drugs and Lactation Database (LactMed)

毒理性

• 蛋白质结合

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

吸收、分配和排泄

• 吸收

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

吸收、分配和排泄

• 消除途径

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

吸收、分配和排泄

• 分布容积

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

吸收、分配和排泄

• 清除

要查阅L-肾上腺素的药代动力学数据，请参考[DB00668]的药物条目。

To refer to the pharmacokinetic data of L-epinephrine, refer to the drug entry for [DB00668].

来源:DrugBank

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  T
• 安全说明：
  S26,S36/37,S45
• 危险类别码：
  R24,R36/37/38
• WGK Germany：
  3
• 危险品运输编号：
  UN 2811 6.1/PG 2
• 海关编码：
  2922509090
• 危险类别：
  6.1(b)
• RTECS号：
  DO2975000
• 包装等级：
  III
• 储存条件：
  密封避光保存。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name DL-Adrenaline
Portland OR
Synonym DL-Epinephrine
Chemical Formula C9H13NO3
CAS Number 329-65-7

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Section II. Composition and Information on Ingredients
Toxicology Data
Chemical Name CAS Number Percent (%) TLV/PEL
DL-Adrenaline 329-65-7 Min. 98.0 (T) Not available. Rat LD50 (intravenous) 0.07 mg/kg
Mouse LD50 (intraperitoneal) 7.8
mg/kg
Mouse LD50 (intravenous) 3.4
mg/kg

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Section III. Hazards Identification
Acute Health Effects Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always 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.
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or
many human organs.

---

Section IV. First Aid Measures
Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
Eye Contact
minutes. Get medical attention.
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing
Skin Contact
and shoes. Wash clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
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, perform mouth-to-mouth
resuscitation. 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.

---

Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
Not available.
Combustion Products These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NO, NO2).
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
and Instructions
Continued on Next Page
DL-Adrenaline
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
Consult with local fire authorities before attempting large scale fire-fighting operations.

---

Section VI. Accidental Release Measures
Spill Cleanup Toxic material. Teratogenic material. Irritating material. Light sensitive material. Heat sensitive material.
Stop leak if without risk. DO NOT get water inside container. DO NOT touch spilled material. Use water spray to reduce
Instructions
vapors. Prevent entry into sewers, basements or confined areas; dike if needed. Eliminate all sources of ignition. Consult
federal, state, and/or local authorities for assistance on disposal.

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Section VII. Handling and Storage
TOXIC. TERATOGEN. IRRITANT. LIGHT SENSITIVE. HEAT SENSITIVE. REFRIGERATE. Keep locked up. Keep away
Handling and Storage
from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a dry, cool place. Avoid
Information
excessive heat and light. DO NOT ingest. Do not breathe dust. Wear suitable protective clothing. If ingested, seek medical
advice immediately and show the container or the label. Treat symptomatically and supportively.
Always store away from incompatible compounds such as oxidizing agents, acids.

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
Personal Protection
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
Solid. (Crystal, powder. Pale yellow - Solubility
Physical state @ 20°C Not available.
greyish yellow red.)
Not available.
Specific Gravity
Molecular Weight 183.20 Partition Coefficient Not available.
Boiling Point Not available. Not applicable.
Vapor Pressure
Melting Point 197°C (386.6°F) Vapor Density Not available.
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Not available.
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data

---

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

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Section XI. Toxicological Information
RTECS Number DO2975000
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Rat LD50 (intravenous) 0.07 mg/kg
Toxicity Data
Mouse LD50 (intraperitoneal) 7.8 mg/kg
Mouse LD50 (intravenous) 3.4 mg/kg
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or many
human organs.
Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Acute Toxic Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Continued on Next Page
DL-Adrenaline

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

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
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 the substance.

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Section XIV. Transport Information
DOT Classification DOT CLASS 6.1: Toxic material.
PIN Number
Proper Shipping Name Toxic solid, organic, n.o.s.
II
Packing Group (PG)
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 CLASS D-1B: Material causing immediate and serious toxic effects (TOXIC).
On DSL.
(Canada)
EINECS Number (EEC) 206-347-6
EEC Risk Statements R23/24/25- Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38- Irritating to eyes, respiratory system and skin.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性方面，DL-肾上腺素是一种激素，由肾上腺髓质分泌，同时它也是一种神经递质。其主要作用靶点为去甲肾上腺受体。

反应信息

• 作为反应物：
  描述：

  消旋肾上腺素 在 pseudooctahedral quaterpyridineiron(III) complex bound to sodium poly(L-glutamate) 、 双氧水 作用下， 生成 肾上腺素红
  参考文献：
  名称：

  Pispisa, Basilio; Palleschi, Antonio; Paradossi, Gaio, Gazzetta Chimica Italiana, 1986, vol. 116, # 8, p. 423 - 430

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(1-羟基-2-(甲基氨基)乙基)苯酚 在 二羟基富马酸 、 acetate buffer 、 氧气 、 horse radish peroxidase 作用下， 生成 消旋肾上腺素
  参考文献：
  名称：

  Preparative hydroxylation of aromatic compounds catalyzed by peroxidase

  摘要：

  DOI：

  10.1021/ja00410a067

文献信息

• Compositions for Treatment of Cystic Fibrosis and Other Chronic Diseases
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20150231142A1

  公开（公告）日：2015-08-20

  The present invention relates to pharmaceutical compositions comprising an inhibitor of epithelial sodium channel activity in combination with at least one ABC Transporter modulator compound of Formula A, Formula B, Formula C, or Formula D. The invention also relates to pharmaceutical formulations thereof, and to methods of using such compositions in the treatment of CFTR mediated diseases, particularly cystic fibrosis using the pharmaceutical combination compositions.

  本发明涉及含有上皮钠通道活性抑制剂与至少一种ABC转运蛋白调节剂化合物（A式、B式、C式或D式）的药物组合物。该发明还涉及这些药物配方，以及使用这些组合物治疗CFTR介导的疾病，特别是囊性纤维化的方法。
• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2017012647A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds according to Formula (I), wherein R1, R3, R4, R5, L1, and Cy are as defined herein. The present invention also provides compounds, methods for the production of said compounds of the invention, pharmaceutical compositions comprising the same and their use in allergic or inflammatory conditions, autoimmune diseases, proliferative diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformations, and/or diseases associated with hypersecretion of IL6 and/or interferons. The present invention also methods for the prevention and/or treatment of the aforementioned diseases by administering a compound of the invention.

  本发明公开了根据式（I）的化合物，其中R1、R3、R4、R5、L1和Cy如本文所定义。本发明还提供了该发明的化合物、制备该化合物的方法、包括相同化合物的药物组合物以及它们在过敏或炎症症状、自身免疫疾病、增殖性疾病、移植排斥、涉及软骨周转障碍的疾病、先天软骨畸形和/或与IL6和/或干扰素过度分泌相关的疾病中的使用。本发明还提供了通过给予该发明的化合物来预防和/或治疗上述疾病的方法。
• [EN] COMPOUNDS THAT MODULATE EGFR ACTIVITY AND METHODS FOR TREATING OR PREVENTING CONDITIONS THEREWITH<br/>[FR] COMPOSÉS MODULANT L'ACTIVITÉ DES RÉCEPTEURS EGFR ET MÉTHODES POUR TRAITER OU PRÉVENIR DES TROUBLES À L'AIDE DE CEUX-CI
  申请人：GATEKEEPER PHARMACEUTICALS INC

  公开号：WO2011140338A1

  公开（公告）日：2011-11-10

  Provided are compounds and methods for treating or preventing kinase-mediated disorders therewith.

  提供了用于治疗或预防激酶介导的疾病的化合物和方法。
• [EN] KINASE INHIBITORS FOR THE TREATMENT OF DISEASE<br/>[FR] INHIBITEURS DE KINASE POUR LE TRAITEMENT D'UNE MALADIE
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2015006492A1

  公开（公告）日：2015-01-15

  The invention relates to compounds and their use in the treatment of disease. Novel irreversible inhibitors of wild-type and mutant forms of EGFR, FGFR, ALK, ROS, JAK, BTK, BLK, ITK, TEC, and/or TXK and their use for the treatment of cell proliferation disorders are described.

  这项发明涉及化合物及其在治疗疾病中的应用。描述了用于治疗细胞增殖紊乱的新型EGFR、FGFR、ALK、ROS、JAK、BTK、BLK、ITK、TEC和/或TXK的野生型和突变型不可逆抑制剂及其应用。
• SUBSTITUTED INDOLES
  申请人：Gant Thomas G.

  公开号：US20090191183A1

  公开（公告）日：2009-07-30

  Disclosed herein are substituted indole cysteinyl leukotriene receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

  本文揭示了Formula I的替代吲哚半胱氨酸白三烯受体调节剂，其制备方法，药物组合物以及使用方法。

表征谱图