(S)-O-去甲基雷氯必利 | 119670-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-O-去甲基雷氯必利
• 中文别名: 3,5-二氯-N-[(1-乙基-2-吡咯烷基)甲基]-2,6-二羟基苯甲酰胺；O-去甲基雷氯必利；去甲基雷氯必利
• 英文名称: (S)-(-)-3,5-dichloro-N-((1-ethyl-2-pyrrolidinyl)methyl)-2,6-dihydroxybenzamide
• 英文别名: O-desmethylraclopride；desmethyl raclopride；nor-raclopride；desmethyl-raclopride；norraclopride；Desmethylraclopride；3,5-dichloro-N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2,6-dihydroxybenzamide
• CAS: 119670-11-0
• 化学式: C₁₄H₁₈Cl₂N₂O₃
• 分子量: 333.215
• InChiKey: DPQOMEPZWBXAMA-QMMMGPOBSA-N

物化性质

• 熔点：
  221.0 to 225.0 °C
• 沸点：
  411.3±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)
• 溶解度：
  在水中的溶解度10 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2933990090
• 储存条件：
  室温

SDS

(S)-O-Desmethylraclopride
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: (S)-O-Desmethylraclopride
5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: (S)-O-Desmethylraclopride
Percent: >98.0%(HPLC)(T)
CAS Number: 119670-11-0
Synonyms: (S)-3,5-Dichloro-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dihydroxybenzamide
Chemical Formula: C14H18Cl2N2O3

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
(S)-O-Desmethylraclopride

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Section 5. FIRE-FIGHTING MEASURES
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use personal protective equipment. Keep people away from and upwind of spill/leak.
Personal precautions,
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
Colour: White - Slightly pale yellow
Odour: No data available
pH: No data available
Melting point/freezing point:223°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
No data available
Relative density:
Solubility(ies):
No data available
[Water]
[Other solvents]
Dilute hydrochloric acid
Very slightly
soluble:
(S)-O-Desmethylraclopride

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
No data available
NTP =
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with 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 the substance.

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Section 14. TRANSPORT INFORMATION
Does not correspond to the classification standard of the United Nations
Hazards Class:
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
(S)-O-Desmethylraclopride

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (S)-O-去甲基雷氯必利 、 碘甲烷 在 sodium hydroxide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 0.08h， 以5.8%的产率得到雷氯必利
  参考文献：
  名称：

  [11C]raclopride（一种正电子发射断层扫描放射性示踪剂）在微流控芯片上的连续流动合成

  摘要：

  11C 标记的放射性示踪剂（如 [11C]raclopride）的生产过程可能需要 45 到 60 分钟才能完成。这些传统方法可以消耗 11C (t1/...

  DOI：

  10.1139/cjc-2012-0331
• 作为产物：
  描述：

  雷氯必利 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 以50%的产率得到(S)-O-去甲基雷氯必利
  参考文献：
  名称：

  Langer; Dolle; Halldin, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S366-S368

  摘要：

  DOI：

文献信息

• Precursor synthesis and radiolabelling of the dopamine D2 receptor ligand [11C]raclopride from [11C]methyl triflate
  作者：Oliver Langer、Kjell Någren、Frédéric Dolle、Camilla Lundkvist、Johan Sandell、Carl-Gunnar Swahn、Françoise Vaufrey、Christian Crouzel、Bernard Maziere、Christer Halldin

  DOI：10.1002/(sici)1099-1344(199912)42:12<1183::aid-jlcr274>3.0.co;2-z

  日期：1999.12

  [11C]raclopride from [11C]methyl triflate. Conditions for the radiolabelling were optimized to obtain a simple and reproducible procedure suitable for automation. [11C]Raclopride was prepared with an average radiochemical yield of 55–65% (decay corrected, based on starting [11C]methyl triflate) in a total synthesis time (including purification and formulation of product) of 35 min. The radiolabelling procedure used

  Desmethyl-raclopride 通过简单的三步合成方法合成，并用于从 [11C] 三氟甲磺酸甲酯制备 [11C] raclopride。优化放射性标记的条件以获得适合自动化的简单且可重复的程序。[11C]Raclopride 的平均放射化学产率为 55-65%（衰减校正，基于起始的 [11C] 三氟甲磺酸甲酯），总合成时间（包括产品的纯化和配方）为 35 分钟。放射性标记程序使用的前体显着减少，避免使用 DMSO，并且与使用 [11C] 甲基碘的标准放射性标记程序相比更短。版权所有 © 1999 John Wiley & Sons, Ltd.
• Application of Microreactor to the Preparation of C-11-Labeled Compounds &lt;i&gt;via&lt;/i&gt; &lt;i&gt;O&lt;/i&gt;-[&lt;sup&gt;11&lt;/sup&gt;C]Methylation with [&lt;sup&gt;11&lt;/sup&gt;C]CH&lt;sub&gt;3&lt;/sub&gt;I: Rapid Synthesis of [&lt;sup&gt;11&lt;/sup&gt;C]Raclopride
  作者：Hidekazu Kawashima、Hiroyuki Kimura、Yuta Nakaya、Kenji Tomatsu、Kenji Arimitsu、Hiroaki Nakanishi、Eiichi Ozeki、Yuji Kuge、Hideo Saji

  DOI：10.1248/cpb.c15-00365

  日期：——

  A new radiolabeling method using a microreactor was developed for the rapid synthesis of [11C]raclopride. A chip bearing a Y-shaped mixing junction with a 200 µm (width)×20 µm (depth)×250 mm (length) flow channel was designed, and the efficiency of O-[11C]methylation was evaluated. Dimethyl sulfoxide solutions containing the O-desmethyl precursor or [11C]CH3I were introduced into separate injection ports by infusion syringes, and the radiochemical yields were measured under various conditions. The decay-corrected radiochemical yield of microreactor-derived [11C]raclopride reached 12% in 20 s at 25°C, which was observed to increase with increasing temperature. In contrast, batch synthesis at 25°C produced a yield of 5%: this indicates that this device could effectively achieve O-[11C]methylation in a shorter period of time. The microreactor technique may facilitate simple and efficient routine production of 11C-labeled compounds via O-[11C]methylation with [11C]CH3I.

  为快速合成 [11C]raclopride 开发了一种使用微反应器的放射性标记新方法。该方法设计了一个带有 Y 形混合结的芯片，其流道为 200 微米（宽）×20 微米（深）×250 毫米（长），并对 O-[11C]甲基化的效率进行了评估。通过输液注射器将含有 O-去甲基前体或 [11C]CH3I 的二甲基亚砜溶液分别注入不同的注入口，并在不同条件下测量放射化学产率。在 25°C 温度下，微反应器衍生的[11C]拉克必利的衰变校正放射化学产率在 20 秒内达到 12%，而且随着温度的升高而增加。相比之下，在 25°C 温度下批量合成的产率为 5%：这表明该装置可以在更短的时间内有效实现 O-[11C]甲基化。该微反应器技术可通过[11C]CH3I 的 O-[11C]methylation 简单高效地实现 11C 标记化合物的常规生产。
• An Improved Synthesis of PET Dopamine D₂ Receptors Radioligand [¹¹C]Raclopride
  作者：Xiangshu Fei、Bruce H. Mock、Timothy R. DeGrado、Ji‐Quan Wang、Barbara E. Glick‐Wilson、Michael L. Sullivan、Gary D. Hutchins、Qi‐Huang Zheng

  DOI：10.1081/scc-120034174

  日期：2004.12.31

  An improved synthesis of [C-11]raclopride is reported. The precursor desmethyl-raclopride was synthesized from 3,5-dichloro-2,6-dimethoxybenzoic acid and (S)-(-)-2-aminoethyl-1-ethylpyrrolidine via a straightforward, four-step synthetic approach with 29% overall chemical yield. [C-11]Raclopride was prepared by O-[C-11]methylation of the precursor with [C-11]methyl triflate and purification with a semi-preparative HPLC method in 20-34% radiochemical yield, based on [C-11]methyl bromide, decay corrected to end of bombardment (EOB).
• Gillings, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S894-S895
  作者：Gillings

  DOI：——

  日期：——
• EHRIN E.; GAWELL L.; DE HOGBERG TH.; PAULIS T.; STROM P., J. LABELL. COMPOUNDS AND RADIOPHARM., 24,(1987) N 8, 931-940
  作者：EHRIN E.、 GAWELL L.、 DE HOGBERG TH.、 PAULIS T.、 STROM P.

  DOI：——

  日期：——