(E)-(+/-)-2-氨基-4-甲基-5-磷-3-戊烯酸 | 127910-31-0

• 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: (E)-(+/-)-2-氨基-4-甲基-5-磷-3-戊烯酸
• 中文别名: (3E)-2-氨基-4-甲基-5-膦酰-3-戊烯酸；（E）-（±）-2-氨基-4-甲基-5-膦基-3-戊烯酸
• 英文名称: DL-(E)-2-amino-4-methyl-5-phosphono-3-pentenoic acid
• 英文别名: CGP 37849；(R,S)-(E)-2-amino-4-methyl-5-phosphono-3-pentenoic acid；D,L-(E)-2-amino-4-methyl-5-phosphono-3-pentenoic acid；DL-[E]-2-amino-4-methyl-5-phosphono-3-pentenoic acid；D,L-(E)-2-amino-4-methylphosphono-3-pentanoic acid；DL-(E)-2-amino-4-methyl-phosphono-3-pentenoic acid；(E)-2-amino-4-methyl-5-phosphonopent-3-enoic acid
• CAS: 127910-31-0
• 化学式: C₆H₁₂NO₅P
• 分子量: 209.139
• InChiKey: BDYHNCZIGYIOGJ-DUXPYHPUSA-N

物化性质

• 沸点：
  523.1±60.0 °C(Predicted)
• 密度：
  1.506±0.06 g/cm3(Predicted)
• 溶解度：
  在水中的溶解度为≥2mg/mL（加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 储存条件：
  储存条件：2-8℃，干燥处，密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : CGP 37849
CAS-No. : 127910-31-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : (3E)-2-amino-4-methyl-5-phosphono-3-pentanoic acid
Formula : C6H12NO5P
Molecular Weight : 209,14 g/mol
Component Concentration
DL-2-Amino-4-methyl-5-phosphono-3-pentenoic acid
CAS-No. 127910-31-0 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: 2 - 8 °C
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
no data available
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

生物活性

CGP 37849 是一种有效的竞争性口服活性 N-甲基-D-天冬氨酸 (NMDA) 受体拮抗剂。它在啮齿动物中表现出抗惊厥、抗抑郁和抗焦虑作用。

体外研究

在体外，CGP 37849 在海马切片中选择性且可逆地对抗 NMDA 所引发的 CA1 锥状细胞放电率增加。在低 Mg²⁺浓度的培养基中，高达 10 μM 的 CGP 37849 可抑制由 Schaffer 联络纤维刺激所引起的 CA1 神经元突发性放电，而不影响初始群体尖峰的大小。

体内研究

CGP 37849 坚强有力地 (Ki 为 220 nM) 并竞争性地抑制 NMDA 敏感的 l-[3H]-谷氨酸与大鼠脑后突触致密区（PSD）片段结合。它还抑制选择性的 NMDA 受体拮抗剂 [3H]-(±)-3-(2-羧基哌嗪-4-基)丙基-1-膦酸 (CPP) 的结合，Ki 为 35 nM。

在体内实验中，向大鼠口服 CGP 37849 可特异性地阻断由离子载体应用的 NMDA 所引起的海马神经元放电，而不影响其对 quisqualate 或 kainate 的反应。给小鼠口服 CGP 37849 可以抑制最大电击诱发的癫痫发作，ED₅₀ 值为 21 mg/kg。

反应信息

• 作为反应物：
  描述：

  (E)-(+/-)-2-氨基-4-甲基-5-磷-3-戊烯酸 在 methyloxirane 作用下， 以 乙醇 为溶剂， 生成 CGP 39551
  参考文献：
  名称：

  Unsaturated amino acids

  摘要：

  该发明涉及式I的不饱和氨基酸##STR1##其中R.sup.1代表羟基或醚化羟基，R.sup.2代表氢、烷基、羟基或醚化羟基，R.sup.3代表氢、烷基、卤代烷基、羟基烷基、较低烷氧基烷基、芳基烷基、较低烯基、卤素或芳基，R.sup.4代表氢、烷基或芳基，R.sup.5代表氢或烷基，R.sup.6代表羧基或酯化或酰胺化的羧基，R.sup.7代表氨基或被烷基或酰基取代的氨基，A代表未取代或烷基取代的α，ω-烷基，其碳原子数为1至3，或代表键，B代表亚甲基或键，但A不是键时B代表键，以及其盐。它们可以通过Michaelis-Arbuzov反应等方法制造，并可用作药理活性物质。

  公开号：

  US05051413A1
• 作为产物：
  描述：

  E-2-formylamino-4-methyl-5-diethylphosphono-3-pentenoic acid ethyl ester 生成 (E)-(+/-)-2-氨基-4-甲基-5-磷-3-戊烯酸
  参考文献：
  名称：

  Unsaturated amino acids

  摘要：

  该发明涉及式I的不饱和氨基酸##STR1##其中R.sup.1代表羟基或醚化羟基，R.sup.2代表氢、烷基、羟基或醚化羟基，R.sup.3代表氢、烷基、卤代烷基、羟基烷基、较低烷氧基烷基、芳基烷基、较低烯基、卤素或芳基，R.sup.4代表氢、烷基或芳基，R.sup.5代表氢或烷基，R.sup.6代表羧基或酯化或酰胺化的羧基，R.sup.7代表氨基或被烷基或酰基取代的氨基，A代表未取代或烷基取代的α，ω-烷基，其碳原子数为1至3，或代表键，B代表亚甲基或键，但A不是键时B代表键，以及其盐。它们可以通过Michaelis-Arbuzov反应等方法制造，并可用作药理活性物质。

  公开号：

  US05051413A1

文献信息

• Methods for the preparation of {2-[(8,9)-dioxo-2,6-diaza-bicyclo[5.2.0]-non-1(7)-en-2-yl[ethyl} phosphonic acid and esters thereof
  申请人：Wilk K. Bogdan

  公开号：US20050090470A1

  公开（公告）日：2005-04-28

  The present invention provides methods for the preparation of 2-[(8,9)-dioxo-2,6-diaza-bicyclo[5.2.0]-non-1 (7)-en-2-yl]ethyl}phosphonic acid, and esters thereof.

  本发明提供了制备2-[(8,9)-二氧化-2,6-二氮杂双环[5.2.0]-壬-1(7)-烯-2-基]乙基}膦酸及其酯的方法。
• Ungesättigte Aminosäuren
  申请人：CIBA-GEIGY AG

  公开号：EP0233154A2

  公开（公告）日：1987-08-19

  Die Erfindung betrifft ungesättigte Aminosäuen der Formel I, worin R¹ Hydroxy oder verethertes Hydroxy bedeutet, R² Wasserstoff, Alkyl, Hydroxy oder verethertes Hydroxy bedeutet, R³ Wasserstoff, Alkyl, Halogenalkyl, Hydroxyalkyl, Niederalkoxyalkyl, Arylalkyl, Niederalkenyl, Halogen oder Aryl bedeutet, R⁴ für Wasserstoff, Alkyl oder Aryl steht, R⁵ Wasserstoff oder Alkyl bedeutet, R⁶ für Carboxy, verestertes oder amidiertes Carboxy steht, R⁷ für Amino oder durch Alkyl oder Acyl substituiertes Amino steht, A für unsubstituiertes oder durch Alkyl substituiertes α,ω-Alkylen mit 1 bis 3 Kohlenstoff­atomen steht oder eine Bindung bedeutet, B Methylen oder eine Bindung bedeutet, mit der Massgabe, dass A von einer Bindung verschieden ist, wenn B eine Bindung bedeutet, sowie Salze davon. Sie können z.B. nach der Michaelis-Arbuzov-Reaktion hergestellt werden und lassen sich als pharmakologische Wirkstoffe verwenden.

  本发明涉及式 I 的不饱和氨基酸、 其中 R¹ 是羟基或醚化羟基，R² 是氢、烷基、羟基或醚化羟基，R³ 是氢、烷基、卤代烷基、羟基烷基、低级烷氧基烷基、芳基烷基、低级烯基、卤素或芳基，R⁴ 是氢、烷基或芳基，R⁵ 是氢或烷基，R⁶ 是羧基、酯化羧基或酰胺化羧基、R⁷ 代表氨基或被烷基或酰基取代的氨基，A 代表未取代或被烷基取代的具有 1 至 3 个碳原子的 α、ω-亚烷基或代表键，B 代表亚甲基或代表键，但条件是当 B 代表键时，A 不同于键，以及它们的盐。例如，它们可以根据迈克尔斯-阿尔布佐夫反应制备，并可用作药剂。
• Verfahren zur Herstellung neuer ungesättigter Aminosäureverbindungen
  申请人：CIBA-GEIGY AG

  公开号：EP0302826A2

  公开（公告）日：1989-02-08

  Die Erfindung betrifft Verfahren zur Herstellung ungesättigter Aminosäureverbindungen der Formel worin R1 Wasserstoff, Alkyl oder Hydroxy bedeutet, R2 Wasserstoff, Alkyl, Halogenniederalkyl, Hydroxyniederalkyl, Niederalkoxyniederalkyl, Arylniederalkyl, Niederalkenyl, Halogen oder Aryl bedeutet, R3 für Wasserstoff, Alkyl oder Aryl steht, R4 Wasserstoff oder Alkyl bedeutet, R5 für gegebenenfalls verestertes oder amidiertes Carboxy steht, R6 eine unsubstituierte durch Niederalkyl oder Arylniederalkyl substituierte Aminogruppe darstellt, A unsubstituiertes oder durch Alkyl substituiertes a,m-Alkylen mit 1 bis 3 Kohlenstoffatomen (C-Atomen) oder eine direkte Bindung darstellt und B Methylen oder eine Bindung bedeutet, mit der Massgabe, dass A unsubstituiertes oder durch Alkyl substituiertes α,ω-Alkylen mit 1 bis 3 C-Atomen darstellt, wenn B für eine direkte Bindung steht, und ihrer Salze, dadurch gekennzeichnet, dass man in einer Verbindung der Formel worin Z1 gegebenenfalls geschütztes Hydroxy bedeutet, Z2 eine Gruppe R1 oder geschütztes Hydroxy bedeutet, Z5 eine Gruppe R5 oder geschütztes Carboxy bedeutet, Z6 eine geschützte Gruppe R6 darstellt und R1, R2, R3, R4, R5, R6, A und B die vorstehend angegebenen Bedeutungen haben, die geschützten Gruppe Z6 und gegebenenfalls Z1, Z2 und/oder Z5 durch Behandeln mit einem Triniederalkylhalogensilan freisetzt und gewünschtenfalls die erhaltene Verbindung in eine andere Verbindung der Formel 1 umwandelt, ein erhaltenes Gemisch optischer Isomeren in die Komponenten auftrennt und das gewünschte Isomer abtrennt und/oder eine erhaltene freie Verbindung in ein Salz oder ein erhaltenes Salz in die freie Verbindung oder in ein anderes Salz überführt. Die Erfindung betrifft auch den (2R)-E-2-Amino-4-methyl-5-phosphono-3-pentensäureethylester und seine Salze.

  本发明涉及一种制备不饱和氨基酸化合物的工艺，其式如下 其中 R1 是氢、烷基或羟基，R2 是氢、烷基、卤代低级烷基、羟基低级烷基、低级烷氧基低级烷基、芳基低级烷基、低级烯基、卤素或芳基，R3 是氢、烷基或芳基，R4 是氢或烷基，R5 是任选酯化或酰胺化的羧基，R6 是被低级烷基或芳基低级烷基取代的未取代氨基、A 代表未取代的或烷基取代的具有 1 至 3 个碳原子（C 原子）的 a、m-亚烷基或直接键，B 代表亚甲基或键，但当 B 代表直接键时，A 代表未取代的或烷基取代的具有 1 至 3 个 C 原子的 α、ω-亚烷基，以及它们的盐，其特征在于，在式化合物中 其中 Z1 是可选的受保护羟基，Z2 是基团 R1 或受保护羟基，Z5 是基团 R5 或受保护羧基，Z6 是受保护基团 R6，且 R1、R2、R3、R4、R5、R6、A 和 B 具有上述含义，受保护基团 Z6 和可选的 Z1、Z2 和/或 Z5，用低级烷基卤代硅烷处理，如果需要，将所得化合物转化为另一种式 1 化合物，将所得光学异构体混合物分离为各组分并分离出所需异构体，和/或将所得游离化合物转化为盐，或将所得盐转化为游离化合物或另一种盐。本发明还涉及(2R)-E-2-氨基-4-甲基-5-膦酰基-3-戊烯酸乙酯及其盐。
• Use of combined excitatory amino acid and cholinergic antagonists to prevent neurological deterioration
  申请人：Olney, John William

  公开号：EP0424179A2

  公开（公告）日：1991-04-24

  The neurotoxic effects of NMDA antagonists are reduced by administering, in conjunction with an NMDA antagonist, an anti-cholinergic agent which is capable of penetrating the blood-brain barrier and which exerts a pharmaceutically antagonistic effect on cholinergic receptors of the muscarinic type on the surfaces of neurons in the central nervous system. Also, excitotoxic damage to neurons in a mammalian central nervous system is reduced by the administration of: (a) an NMDA antagonist which penetrates blood-brain barriers in quantities sufficient to inhibit the functioning of NMDA receptors; and (b) a non-NMDA antagonist which penetrates blood-brain barriers in quantities sufficient to inhibit the functioning of at least one type of non-NMDA receptor.

  在使用 NMDA 拮抗剂的同时，还可以使用一种抗胆碱能药物，这种药物能够穿透血脑屏障，并对中枢神经系统神经元表面的毒蕈碱型胆碱能受体产生药理拮抗作用，从而减少 NMDA 拮抗剂的神经毒性作用。此外，哺乳动物中枢神经系统神经元的兴奋毒性损伤也可通过服用以下药物而减轻： (a) 一种 NMDA 拮抗剂，它能穿透血脑屏障，足以抑制 NMDA 受体的功能；以及 (b) 非 NMDA 拮抗剂，其穿透血脑屏障的量足以抑制至少一种非 NMDA 受体的功能。
• Excitatory amino acid antagonists as anti-emetic drugs
  申请人：Olney, John William

  公开号：EP0432994A2

  公开（公告）日：1991-06-19

  Emesis may be suppressed by administering at least one compound which antagonizes the activity of at least one type of excitatory amino acid receptor on the surfaces of neurons in or adjacent to circumventricular organs in the central nervous system.

  至少有一种化合物可以拮抗中枢神经系统中环状器官或邻近环状器官的神经元表面上至少一种兴奋性氨基酸受体的活性，从而抑制呕吐。