N-乙酰基-D-青霉胺 | 59-53-0

• 物质功能分类: 原料药 - 抗生素类药物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-乙酰基-D-青霉胺
• 中文别名: N-乙酰-DL-青霉胺；N-乙酰基-DL-青霉胺；N-乙酰基-3-巯基-D-缬氨酸；N-乙酰青霉胺；乙酰青霉胺
• 英文名称: NAP
• 英文别名: N-Acetyl-DL-penicillamin；N-Acetyl-dl-penicillamine；2-acetamido-3-methyl-3-sulfanylbutanoic acid
• CAS: 59-53-0
• 化学式: C₇H₁₃NO₃S
• mdl: MFCD00004855
• 分子量: 191.251
• InChiKey: MNNBCKASUFBXCO-UHFFFAOYSA-N

物化性质

• 熔点：
  186-189 °C (dec.)(lit.)
• 密度：
  1.2684 (rough estimate)
• 溶解度：
  DMF: 30 mg/ml,DMSO: 30 mg/ml,DMSO:PBS (pH 7.2) (1:7): 0.12 mg/ml,乙醇: 5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  67.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• 储存条件：
  充氩气密封并在4℃下干燥保存。

SDS

Name:	N-Acetyl-DL-Penicillamine 98% Material Safety Data Sheet
Synonym:	N-Acetyl-3-Mercaptovaline
CAS:	59-53-0

Section 1 - Chemical Product MSDS Name:N-Acetyl-DL-Penicillamine 98% Material Safety Data Sheet
Synonym:N-Acetyl-3-Mercaptovaline

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
59-53-0	N-Acetyl-DL-Penicillamine	98	200-434-2

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.Moisture sensitive.Light sensitive.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. Mercaptans may cause nausea and headache. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse. Mercaptans may cause nausea and headache.
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.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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. Do NOT get water inside containers. 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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation. Do not get water inside containers.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Store protected from light. Do not allow contact with water. Keep from contact with moist air and steam.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture. Store protected from light.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 59-53-0: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Crystalline powder
Color: white crystalline powder
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 188.00 - 189.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: (CH3)2C(SH)CH(NHCOCH3)CO2H
Molecular Weight: 191.24

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, light, dust generation, moisture, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Moisture, heat, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 59-53-0: YV9380000 LD50/LC50:
CAS# 59-53-0: Oral, rat: LD50 = >956 mg/kg.
Carcinogenicity:
N-Acetyl-DL-Penicillamine - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
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# 59-53-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 59-53-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 59-53-0 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

用途

乙酰青霉胺主要用于治疗类风湿性关节炎、慢性迁延性肝炎、硬皮病和口眼干燥综合征等自身免疫性疾病。此外，它还广泛应用于铜离子在各组织中沉积导致的肝豆状核变性，并对铅、汞中毒具有解毒作用。乙酰青霉胺也是制备青霉胺的一种中间体化合物。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  N-乙酰基-D-青霉胺	N-acetyl-D-penicillamine	15537-71-0	C7H13NO3S	191.251
  ——	N-acetylpenicillamine methyl ester	39239-85-5	C8H15NO3S	205.278
  S-亚硝基-N-乙酰-DL-青霉胺	S-nitroso-N-acetyl-DL-penicillamine	67776-06-1	C7H12N2O4S	220.249
  ——	N-acetyl-S-benzyl-DL-penicillamine	101115-49-5	C14H19NO3S	281.376

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  N-乙酰基-D-青霉胺	N-acetyl-D-penicillamine	15537-71-0	C7H13NO3S	191.251
  ——	N-acetylpenicillamine methyl ester	39239-85-5	C8H15NO3S	205.278
  ——	N-acetyl-S-methyl-DL-penicillamine	34297-29-5	C8H15NO3S	205.278
  N-乙酰基-3-(亚硝基硫代)-D-缬氨酸	S-nitroso-N-acetylpenicillamine	79032-48-7	C7H12N2O4S	220.249
  S-亚硝基-N-乙酰-DL-青霉胺	S-nitroso-N-acetyl-DL-penicillamine	67776-06-1	C7H12N2O4S	220.249
  ——	S-<15N>nitroso-N-acetyl-DL-penicillamine	——	C7H12N2O4S	221.243
  ——	N-acetyl-D,L-penicillamine disulfide	67809-84-1	C14H24N2O6S2	380.486
  ——	α-acetylamino-β-acetyldithioisovaleric acid	109795-73-5	C9H15NO4S2	265.354
  ——	N-acetyl-S-benzyl-DL-penicillamine	101115-49-5	C14H19NO3S	281.376
  5,5-二甲基噻唑烷-4-羧酸	5,5-dimethyl-thiazolidine-4-carboxylic acid	15260-83-0	C6H11NO2S	161.225

反应信息

• 作为反应物：
  描述：

  N-乙酰基-D-青霉胺 在 盐酸 、 硫酸 、 sodium nitrite 作用下， 生成 N-乙酰基-3-(亚硝基硫代)-D-缬氨酸
  参考文献：
  名称：

  Nitric oxide-releasing packaging membranes

  摘要：

  开发并测试了具有抗菌性能的可生物降解复合膜，由纳米纤维素纤维、壳聚糖和硝基乙酰青霉胺（SNAP）组成，用于食品包装应用。硝基氧化物供体SNAP被封装到完全分散的壳聚糖中，与纳米纤维素纤维（CNF）充分混合，制备成复合膜。制备的膜中壳聚糖和SNAP均匀分散在纳米纤维素纤维中，通过扫描电子显微镜（SEM）和化学发光氧化物分析仪确认。没有SNAP的膜的水蒸气透过率低于带有SNAP的膜。添加SNAP导致2层和3层膜结构的杨氏模量降低。SNAP包含的膜的抗菌性能评估显示对肠球菌、金黄色葡萄球菌和李斯特菌的细菌菌株有有效的抑制区，并展示了其在食品包装中的潜在应用。

  公开号：

  US10494493B1
• 作为产物：
  描述：

  S-亚硝基-N-乙酰-DL-青霉胺 在 甲酸 作用下， 以 水 为溶剂， 生成 N-乙酰基-D-青霉胺
  参考文献：
  名称：

  解吸电喷雾电离质谱在线研究水相电化学反应

  摘要：

  电化学（EC）与质谱（MS）的结合是阐明电化学反应机理的强大工具。然而，很少探索直接在线分析水相中的电化学反应。本文介绍了使用脱附电喷雾电离质谱（DESI-MS）在线研究几种与水相具有生物学相关性的电化学反应，例如亚硝基硫醇还原，碳水化合物氧化和卡马西平氧化。已发现亚硝基硫醇[例如，亚硝酰化的胰岛素B（13-23）]的电还原会由于NO的丢失而导致游离硫醇，这是首次通过在线MS分析得到证实。29 Da的特征质量转移和降低的强度提供了快速的方法来鉴定亚硝基化的物质。同样重要的是 碰撞诱导解离（CID）后，还原的肽离子比其亚硝化的前体离子产生更多的碎片离子（推测主链片段无法与前体离子的简便NO竞争），从而促进了肽的测序。在糖氧化的情况下，发现葡萄糖在碱性pH下经历电氧化以产生葡糖酸，而在中性和酸性pH下不发生。对于二糖如麦芽糖和纤维二糖也观察到了这种pH依赖性的电化学行为。经电化学氧化后，发现卡

  DOI：

  10.1007/s13361-015-1210-2

文献信息

• [EN] S-NITROSOMERCAPTO COMPOUNDS AND RELATED DERIVATIVES<br/>[FR] COMPOSÉS DE S-NITROSOMERCAPTO ET DÉRIVÉS APPARENTÉS
  申请人：GALLEON PHARMACEUTICALS INC

  公开号：WO2009151744A1

  公开（公告）日：2009-12-17

  The present invention is directed to mercapto-based and S- nitrosomercapto-based SNO compounds and their derivatives, and their use in treating a lack of normal breathing control, including the treatment of apnea and hypoventilation associated with sleep, obesity, certain medicines and other medical conditions.

  本发明涉及基于巯基和S-亚硝基巯基的SNO化合物及其衍生物，以及它们在治疗正常呼吸控制缺失方面的用途，包括治疗与睡眠、肥胖、某些药物和其他医疗状况相关的呼吸暂停和低通气。
• Uptake Kinetics of Methylmercury in a Freshwater Alga Exposed to Methylmercury Complexes with Environmentally Relevant Thiols
  作者：Aleksandra Skrobonja、Zivan Gojkovic、Anne L. Soerensen、Per-Olof Westlund、Christiane Funk、Erik Björn

  DOI：10.1021/acs.est.9b05164

  日期：2019.12.3

  environment. Rate constants for MeHg interactions with cells were determined for the MeHg-thiol treatments and a control assay containing the thermodynamically less stable MeHgOH complex. We found both elevated amounts of MeHg associated with whole cells and higher MeHg association rate constants in the control compared to the thiol treatments. Furthermore, the association rate constants were lower when

  浮游植物对细胞吸收溶解性甲基汞（MeHg）的吸收是MeHg进入水生食物网的最重要切入点。但是，该过程尚未完全理解。在这项研究中，我们调查了化学形态对淡水绿色微藻小硒硒藻对MeHg积累速率常数的影响。我们使用了六种MeHg-硫醇复合物，它们在环境中通常具有中等但重要的结构差异。对于MeHg-硫醇处理和包含热力学较不稳定的MeHgOH配合物的对照测定，确定了MeHg与细胞相互作用的速率常数。我们发现与硫醇处理相比，与全细胞结合的MeHg量升高，并且在对照中具有较高的MeHg结合率常数。此外，与藻类结构较简单的复合物相比，藻类暴露于具有较大硫醇和更大“支化”化学结构的MeHg复合物时，缔合速率常数较低。结果进一步证明，MeHg络合物在介质中的热力学稳定性和化学结构是MeHg与细胞表面相互作用速率的重要控制因素，而不是跨膜的MeHg交换速率的重要控制因素。我们的结果与摄取机制有关，该机制涉及在内化
• Alkylamine-Substituted Perthiocarbamates: Dual Precursors to Hydropersulfide and Carbonyl Sulfide with Cardioprotective Actions
  作者：Vinayak S. Khodade、Blaze M. Pharoah、Nazareno Paolocci、John P. Toscano

  DOI：10.1021/jacs.9b12180

  日期：2020.3.4

  alkylamine-substituted perthiocarbamates. Triggered by a base-sensitive, self-immolative moiety, these precursors show efficient RSSH release, and also demonstrate the ability to generate carbonyl sulfide (COS) in the presence of thiols. Using this dually reactive alkylamine-substituted perthiocarbamate platform, the generation of both RSSH and COS is tunable with respect to half-life, pH, and availability

  最近在哺乳动物系统中发现的氢过硫化物 (RSSH) 表明它们在细胞信号传导中的潜在作用。然而，由于 RSSH 在生理条件下的不稳定性，对其生物学意义的探索具有挑战性。在此，我们报告了烷基胺取代的全硫代氨基甲酸酯的制备、RSSH 释放特性和细胞保护性质。由碱敏感的自焚部分触发，这些前体显示出有效的 RSSH 释放，并且还证明了在硫醇存在下生成羰基硫 (COS) 的能力。使用这种双反应性烷基胺取代的全硫代氨基甲酸酯平台，RSSH 和 COS 的生成可根据硫醇的半衰期、pH 值和可用性进行调节。重要的，
• [EN] NOVEL THIOPHENE AMIDINES, COMPOSITIONS THEREOF, AND METHODS OF TREATING COMPLEMENT-MEDIATED DISEASES AND CONDITIONS<br/>[FR] NOUVELLES AMIDINES DE THIOPHENE, COMPOSITIONS DE CES AMIDINES ET PROCEDE POUR TRAITER DES MALADIES ET DES ETATS MEDIES PAR LE COMPLEMENT
  申请人：DIMENSIONAL PHARM INC

  公开号：WO2003099805A1

  公开（公告）日：2003-12-04

  Disclosed is a method for treating the symptoms of an acute or chronic disorder mediated by the classical pathway of the complement cascade, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula (I) or a solvate, hydrate or pharmaceutically acceptable salt thereof; wherein R1, R2, R3, R4 and R7 are defined in the specification, Z is SO or SO2, and Ar is an aromatic or heteroaromatic group as defined herein.

  揭示了一种治疗急性或慢性疾病症状的方法，该方法通过补体级联的经典途径介导，包括向需要此类治疗的哺乳动物施用化合物I的治疗有效量或其溶剂化合物、水合物或药用可接受盐；其中规范中定义了R1、R2、R3、R4和R7，Z为SO或SO2，Ar为本规范中定义的芳香族或杂环芳基。
• [EN] DRUGS FOR CHRONIC PAIN<br/>[FR] MEDICAMENTS CONTRE LA DOULEUR CHRONIQUE
  申请人：NICOX SA

  公开号：WO2004054965A1

  公开（公告）日：2004-07-01

  The present invention relates to nitrooxyderivatives or salts thereof having the following general formula (I): R-NR1c -(K)k0-(B)b0-(C)c0-NO2 (I), wherein c0, b0 and k0 are 0 or 1; R is the radical of an analgesic drug for chronic pain, for instance neurophatic pain; R1c, is H or alkyl with from 1 to 5 carbon atoms; B is such that its precursor is selected from amino acids, hydroxy acids, polyalcohol, compounds; C is a bivalent radical containing an aliphatic, heterocyclic or aromatic radical.

  本发明涉及具有以下一般式（I）的硝基氧衍生物或其盐：R-NR1c-(K)k0-(B)b0-(C)c0-NO2（I），其中c0、b0和k0为0或1；R是用于慢性疼痛的镇痛药物的基团，例如神经性疼痛；R1c为H或含有1至5个碳原子的烷基；B的前体选自氨基酸、羟基酸、多元醇、化合物；C是含有脂肪族、杂环或芳香族基团的二价基团。