DL-正肾上腺素盐酸盐 | 55-27-6

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: DL-正肾上腺素盐酸盐
• 中文别名: DL-去甲肾上腺素盐酸盐；去甲肾上腺素盐酸盐；盐酸-DL-去甲肾上腺素；DL-盐酸降肾上腺素；DL-降肾上腺素盐
• 英文名称: norepinephrine hydrochloride
• 英文别名: noradrenaline hydrochloride；dl-norepinephrine hydrochloride；(R/S)-noradrenaline hydrochloride；dl-noradrenaline hydrochloride；(+/-)-arterenol hydrochloride；(±)-1-(3,4-dihydroxyphenyl)-2-aminoethanol hydrochloride；4-(2-amino-1-hydroxyethyl)benzene-1,2-diol;hydron;chloride
• CAS: 55-27-6
• 化学式: C₈H₁₂NO₃*Cl
• mdl: MFCD00012880
• 分子量: 205.641
• InChiKey: FQTFHMSZCSUVEU-UHFFFAOYSA-N

物化性质

• 熔点：
  140-144 °C (dec.)
• 溶解度：
  水：可溶50mg/mL，透明至微浑浊，淡黄色至棕黄色

计算性质

• 辛醇/水分配系数(LogP)：
  -0.68
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  86.7
• 氢给体数：
  5
• 氢受体数：
  4

安全信息

• 危险等级：
  6.1(b)
• 危险品运输编号：
  UN 2811
• WGK Germany：
  3
• 海关编码：
  2922509090
• 危险类别：
  6.1(b)
• 危险类别码：
  R25
• RTECS号：
  DN6650000
• 包装等级：
  III
• 储存条件：
  2-8°C

SDS

Name:	DL-Norepinephrine Hydrochloride 99% Material Safety Data Sheet
Synonym:
CAS:	55-27-6

Section 1 - Chemical Product MSDS Name:DL-Norepinephrine Hydrochloride 99% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
55-27-6	DL-Norepinephrine Hydrochloride	99	200-229-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Inhalation of dust may cause respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use only in a well-ventilated area.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 55-27-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 145.00 - 147.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H11NO3.HCl
Molecular Weight: 205.64

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 55-27-6: DN6650000 LD50/LC50:
Not available.
Carcinogenicity:
DL-Norepinephrine Hydrochloride - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: ALKALOID SALTS, SOLID, N.O.S.*
Hazard Class: 6.1
UN Number: 1544
Packing Group: III
IMO
Shipping Name: ALKALOIDS, SOLID, N.O.S.
Hazard Class: 6.1
UN Number: 1544
Packing Group: III
RID/ADR
Shipping Name: ALKALOID SALTS, SOLID, N.O.S.
Hazard Class: 6.1
UN Number: 1544
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 55-27-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 55-27-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 55-27-6 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

DL-去甲肾上腺素盐酸盐是一种合成苯乙胺，模拟内源性去甲肾上腺素的拟交感神经作用。它是一种靶向α1和β1肾上腺素受体的神经递质，能够降低心内膜下氧分压。

靶点

• IC50: α1 和 β1 肾上腺素受体

反应信息

• 作为反应物：
  描述：

  DL-正肾上腺素盐酸盐 在 sodium disulfite 作用下， 以 水 为溶剂， 以55%的产率得到去甲肾上腺素杂质
  参考文献：
  名称：

  Synthesis and adrenoceptor affinity of some highly polar .beta.-substituted catecholamines

  摘要：

  In order to assess the potential for sympathomimetic or sympatholytic activity within the series of catecholamine beta-sulfonates 3a-c, alpha- and beta-adrenoceptor binding affinities were determined using rat brain homogenate preparations. Furthermore, their potential for indirect activity was assessed by measurement of blockade of norepinephrine uptake into rat synaptosomal preparations. Activity was uniformly low or nonexistent throughout the series. The possibility of unfavorable solution conformational distribution within the series was investigated by examination of the side chain vicinal 1H NMR coupling constants, but no differences that could account for the lack of affinity were found. The observed behavior may be due to receptor intolerance of the bulky beta-sulfonate substituent or an electronic mismatch in which normal H bonding is significantly altered.

  DOI：

  10.1021/jm00142a026
• 作为产物：
  描述：

  2-氨基-3',4'-二羟基苯乙酮盐酸盐 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 45.0 ℃ 、50.0 Pa 条件下， 反应 5.0h， 以96.7%的产率得到DL-正肾上腺素盐酸盐
  参考文献：
  名称：

  [EN] PROCESS FOR PREPARATION OF (DL) -NOREPINEPHRINE ACID ADDITION SALT, A KEY INTERMEDIATE OF (R) - (-) - NOREPINEPHRINE
  [FR] PROCÉDÉ DE PRÉPARATION D'UN SEL D'ADDITION D'ACIDE DE NORÉPINÉPHRINE (DL), INTERMÉDIAIRE CLÉ DE LA NORÉPINÉPHRINE (R) - (-) -

  摘要：

  该发明揭示了一种制备(dl)-去甲肾上腺素盐的方法，通过将3,4-二羟基-α-卤代乙酰苯酮与六亚甲基四胺反应以提供六胺盐；随后进行水解和氢化。该发明还揭示了该过程中形成的一种新型中间体及其合成方法。

  公开号：

  WO2013008247A1

文献信息

• Arylsulfonylaminobenzene derivatives and the use thereof as factor Xa
  申请人：3-Dimensional Pharmaceuticals, Inc.

  公开号：US05741819A1

  公开（公告）日：1998-04-21

  The present invention is directed to non-peptidic factor Xa inhibitors which are useful for the treatment of arterial and venous thrombotic occlusive disorders, inflammation, cancer, and neurodegenerative diseases. The factor Xa inhibitors provide compounds of structure: ##STR1## or pharmaceutically acceptable salts thereof; wherein R.sup.1 is alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, heteroaryl or substituted heteroaryl; R.sup.2 is one of hydrogen, alkyl, cycloalkyl or aryl; R.sup.3 is one of hydrogen, hydroxy or alkoxy; R.sup.4 is one of --NH.sub.2, phenyl or pyridyl, wherein said phenyl and said pyridyl are optionally substituted with one or two of halogen, hydroxy, hydroxyalkyl, alkoxy, amino, monoalkylamino, dialkylamino, aminoalkyl, monoalkylaminoalkyl and/or dialkylaminoalkyl; X is one of --CH.sub.2 -- or --C(O)--; and n is from zero to eleven; provided that when R.sup.4 is --NH.sub.2, then R.sup.3 is hydrogen and n is other than zero; and also provided that when R.sup.3 is hydroxy or alkoxy, then R.sup.4 is other than --NH.sub.2, and n is other than zero.

  本发明涉及用于治疗动脉和静脉血栓性闭塞性疾病、炎症、癌症和神经退行性疾病的非肽因子Xa抑制剂。因子Xa抑制剂提供结构化合物：##STR1##或其药学上可接受的盐；其中R.sup.1是烷基、取代烷基、环烷基、芳基、取代芳基、杂环芳基或取代杂环芳基；R.sup.2是氢、烷基、环烷基或芳基中的一种；R.sup.3是氢、羟基或烷氧基中的一种；R.sup.4是--NH.sub.2、苯基或吡啶基中的一种，其中所述苯基和所述吡啶基可以选择地取代为卤素、羟基、羟基烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氨基烷基、单烷基氨基烷基和/或二烷基氨基烷基中的一种或两种；X是--CH.sub.2--或--C(O)--中的一种；n为零到十一；但是当R.sup.4为--NH.sub.2时，R.sup.3为氢且n不为零；同时当R.sup.3为羟基或烷氧基时，R.sup.4不为--NH.sub.2，且n不为零。
• A New and Efficient Route for the Synthesis of Naturally Occurring Catecholamines
  作者：Roberta Bernini、Fernanda Crisante、Maurizio Barontini、Giancarlo Fabrizi

  DOI：10.1055/s-0029-1217027

  日期：2009.11

  adrenergic receptor antagonists, have been prepared by a regioselective oxidation of the corresponding 4-hydroxyphenethylamine derivatives by 2-iodoxybenzoic acid (IBX) in homogeneous as well as in heterogeneous conditions and followed by cleavage of the amino protective group. By using polymer-supported IBX, after the first oxidation, the oxidant can be recovered, regenerated, and efficiently reused for

  儿茶酚胺，拟交感神经药和肾上腺素能受体拮抗剂已通过2-碘氧基苯甲酸（IBX）在均相和非均相条件下将相应的4-羟基苯乙胺衍生物进行区域选择性氧化，然后裂解氨基保护基来制备。通过使用聚合物支撑的IBX，在第一次氧化后，氧化剂可以被回收，再生并有效地再使用几次。还已经报道了一种合成许多药物关键成分的N-（甲氧基羰基）多巴胺的有效，简便和绿色的方法。 N-（甲氧羰基）多巴胺-儿茶酚胺-芳族羟基化-2-碘氧基苯甲酸-聚合物负载的IBX
• Fluorometric Determination of 1,2,3,4-Tetrahydro-6,7-dihydroxyisoquinoline in Biological Materials by HPLC.
  作者：Akira SHIRAHATA、Masanori YOSHIOKA、Zenzo TAMURA

  DOI：10.1248/cpb.45.1814

  日期：——

  In the belief that endogenous 1, 2, 3, 4-tetrahydro-6, 7-dihydroxyisoquinoline (DA-Fp) could be a potential marker involved in the etiology of various diseases such as Parkinsonism, we attempted to develop a fluorescence method for DA-Fp. It was synthesized by condensation of dopamine with formaldehyde according to an established method.Periodate was identified by screening from various oxidation reagents as a fluorescence reagent to DA-Fp. Optimal reaction conditions were obtained with 0.25 mM NaIO4 in 0.1 M phosphate buffer (pH 8.0) at 37°C for 15 min. The fluorescence spectrum of the derivative showed that we had found a new reaction specific for DA-Fp. This reaction we coupled on-line to high performance liquid chromatography (HPLC), which enabled us to achieve a highly sensitive method for determining DA-Fp. A working curve was linear from 2 to 800 pmol of DA-Fp per injection.To determine DA-Fp in biological materials, the pretreatment before HPLC was optimized by hydrolysis of its conjugate and suppression of the artifact with l-phenylephrine. Urinary excretion of DA-Fp in men was measured by this new present method. The urinary excretion of endogenous DA-Fp increased in a rabbit given L-DOPA. The DA-Fp concentration was determined in rat brain. The significance of DA-Fp in these biological materials is discussed and evaluated. We conclude that the present method will be useful for studying tetrahydroisoquinolines involved in meny diseases.

  由于认为内源性 1, 2, 3, 4-四氢-6, 7-二羟基异喹啉（DA-Fp）可能是帕金森病等多种疾病病因的潜在标志物，我们尝试开发一种 DA-Fp 的荧光方法。通过从各种氧化试剂中筛选，确定高碘酸盐为 DA-Fp 的荧光试剂。最佳反应条件是在 0.1 M 磷酸盐缓冲液（pH 8.0）中加入 0.25 mM NaIO4，在 37°C 下反应 15 分钟。衍生物的荧光光谱显示，我们发现了 DA-Fp 的新特异性反应。我们将该反应与高效液相色谱（HPLC）联用，从而实现了高灵敏度的 DA-Fp 检测方法。为了测定生物材料中的DA-Fp，我们对HPLC前的预处理进行了优化，水解了DA-Fp的共轭物，并用l-苯肾上腺素抑制了伪影。采用这种新方法测定了男性尿液中DA-Fp的排泄量。服用 L-DOPA 的兔子尿液中内源性 DA-Fp 的排泄量增加。测定了大鼠大脑中的 DA-Fp 浓度。我们讨论并评估了 DA-Fp 在这些生物材料中的意义。我们得出结论，本方法将有助于研究与多种疾病相关的四氢异喹啉类化合物。
• [EN] COMPOSITIONS AND METHODS OF REGULATING CANCER RELATED DISORDERS AND DISEASES<br/>[FR] COMPOSITIONS ET MÉTHODES DE RÉGULATION DE TROUBLES ET MALADIES ASSOCIÉS AU CANCER
  申请人：ONCO THERAPIES LLC

  公开号：WO2017070052A1

  公开（公告）日：2017-04-27

  Provided herein are naphthylic derivative compounds, or pharmaceutically acceptable salts thereof, that are useful for inhibiting cancers. Also provided herein are methods of using effective amounts of said compounds, optionally with pharmaceutical carriers, for the treatment of cancers within human subjects.

  本文提供了萘基衍生物化合物或其药用盐，用于抑制癌症。本文还提供了使用有效量的该化合物的方法，可选地与药用载体一起，用于治疗人体内的癌症。
• Reaction of malondialdehyde with amine neurotransmitters. Formation and oxidation chemistry of fluorescent 1,4-dihydropyridine adducts
  作者：Marco d'Ischia、Alessandra Napolitano、Claudio Costantini

  DOI：10.1016/0040-4020(95)00552-j

  日期：1995.8

  Under physiologically relevant conditions, malondialdehyde reacts smoothly with amine neurotransmitters, i.e. dopamine, norepinephrine and serotonin, to give the fluorescent dihydropyridines 1, 4 and 5, respectively, as the relatively most abundant products. Small amounts of enaminal derivatives, such as 2 and 6, could also be obtained in the reactions with dopamine and serotonin. Oxidation of 1 with

  在生理相关条件下，丙二醛与胺神经递质（即多巴胺，去甲肾上腺素和5-羟色胺）平稳反应，分别得到荧光二氢吡啶1、4和5，这是相对最丰富的产物。在与多巴胺和5-羟色胺的反应中也可以获得少量的烯胺衍生物，例如2和6。用过氧化氢/过氧化物酶氧化1会导致形成不稳定产物的复杂模式，不稳定产物的主要成分已被分离并鉴定为邻醌环氧化物7。类似的4和5氧化主要得到二氢吡啶8和4,4 ′-二吲哚基9。这些结果为丙二醛在神经元变性和脂褐素形成中的作用提供了新的线索。

表征谱图