A2A受体选择性拮抗剂,DMPX | 14114-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: A2A受体选择性拮抗剂,DMPX
• 中文别名: 3,7-二甲基-1-炔丙基黄嘌呤；3,7-二甲基-1-丙炔黄嘌呤
• 英文名称: 3,7-dimethyl-1-propargylxanthine
• 英文别名: 3,7-dihydro-3,7-dimethyl-1-(2-propynyl)-1H-purine-2,6-dione；DMPX；3,7-dimethyl-1-(prop-2-yn-1-yl)-3,7-dihydro-1H-purine-2,6-dione；3,7-dimethyl-1-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione；N¹-propargyltheobromine；3,7-dimethyl-1-propargyl xanthine；3,7-dimethyl-1-prop-2-ynylpurine-2,6-dione
• CAS: 14114-46-6
• 化学式: C₁₀H₁₀N₄O₂
• mdl: MFCD00078576
• 分子量: 218.215
• InChiKey: IORPOFJLSIHJOG-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205°C
• 溶解度：
  二甲基亚砜：≥15 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933990090
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  存放在室温、干燥且密封的环境中。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3,7-Dimethyl-1-propargylxanthine
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 14114-46-6
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
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
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
Safety data sheet available on request.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 3,7-Dimethyl-1-(2-propynyl)xanthine
DMPX
Formula : C10H10N4O2
Molecular Weight : 218,21 g/mol
CAS-No. : 14114-46-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3,7-Dimethyl-1-propargylxanthine
CAS-No. 14114-46-6 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3,7-Dimethyl-1-propargylxanthine
CAS-No. 14114-46-6 Xi, R36/37/38 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Carbon oxides, nitrogen oxides (NOx)
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 vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
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.Normal measures for preventive fire
protection.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white, beige
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 204 - 205 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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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 sensitisation
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available
Neurotoxic effects., To the best of our knowledge, the chemical, physical, and toxicological properties have
not been thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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. Contact a licensed
professional waste disposal service to dispose of this material. 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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  A2A受体选择性拮抗剂,DMPX 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 三(2-呋喃基)膦 、 potassium carbonate 、 二环己胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 3.0h， 生成 1-[(2Z)-4-(adamantan-1-ylamino)-3-(pyridin-3-yl)but-2-en-1-yl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  Exploiting adamantane as a versatile organic tecton: multicomponent catalytic cascade reactions

  摘要：

  三元和九元的Pd(0)催化的烯丙烯、芳基碘化物和N-亲核试剂的组装，以及三取代Z-烯烃的同时引入，均可轻松实现。

  DOI：

  10.1039/c2cc35054h
• 作为产物：
  描述：

  可可碱 、 3-溴丙炔 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 A2A受体选择性拮抗剂,DMPX
  参考文献：
  名称：

  铜/石墨烯/粘土纳米杂化物：一种高效多相纳米催化剂，可通过“点击” Huisgen 1,3-偶极环加成反应合成新型1,2,3-三唑基碳环核苷

  摘要：

  一些新颖1个的非常温和的和高效合成ħ三唑carboacyclic核苷- -1,2,3-经由一个“点击”胡伊斯根环加成Ñ使用Cu / aminoclay /还原氧化石墨烯纳米杂化物（铜/ AC -propargyl核碱基和叠氮基醇/ r-GO纳米杂化）作为纳米催化剂的描述。讨论了Cu / AC / r-GO纳米杂化物的制备和表征。该催化剂的特征在于X射线衍射，FT IR，TEM和X射线技术的能量色散分析。Cu / AC / r-GO纳米杂化物是一种稳定且高效的多相纳米催化剂，可通过简单过滤轻松地制备，使用和从反应混合物中恢复，并在许多连续试验中重复使用而活性没有明显降低。

  DOI：

  10.1002/hlca.201500149

文献信息

• Immunosuppressive effects of 8-substituted xanthine derivatives
  申请人：K.U. Leuven Research & Development

  公开号：US07253176B1

  公开（公告）日：2007-08-07

  The invention relates to a novel use of 8-substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders.

  这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。
• Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 6: Synthesis of Sugar, Nucleoside, Purine, Benzodiazepinone and β-lactam Analogues via Capture of in situ Generated Vinylstannanes
  作者：Adele Casaschi、Ronald Grigg、José M. Sansano

  DOI：10.1016/s0040-4020(00)00661-x

  日期：2000.9

  The regioselective palladium catalysed hydrostannylation of alkynes bearing a β-heteroatom affords mainly α-vinyltin(IV) compounds that are used as terminating species in palladium catalysed cyclisation–anion capture processes. The pharmacophore attached to the alkyne moiety permits the synthesis of sugars, nucleosides, purines, benzodiazepinones and β-lactams analogues in good yields.

  带有β-杂原子的炔烃的区域选择性钯催化的氢化锡烷基化主要提供α-乙烯基锡（IV）化合物，这些化合物在钯催化的环化-阴离子捕获过程中用作终止物种。附于炔部分的药效基团允许以高收率合成糖，核苷，嘌呤，苯并二氮杂酮和β-内酰胺类似物。
• Synthesis and Biological Evaluation of Novel 1,2,3-Triazolonucleotides
  作者：Iwona E. Głowacka、Jan Balzarini、Andrzej E. Wróblewski

  DOI：10.1002/ardp.201200421

  日期：2013.4

  The application of microwave irradiation shortened the reaction time to 10 min in comparison to ca. 48 h when 1,3‐dipolar cycloadditions were performed under standard conditions. All compounds were evaluated in vitro for inhibitory activity against a broad variety of DNA and RNA viruses. None of the compounds were antivirally active at subtoxic concentrations. Compound 17k exhibited moderate inhibitory

  详细阐述了从 2-叠氮乙氧基甲基和 2-叠氮乙氧基乙基膦酸二乙酯制备核苷的 1,2,3-三唑类似物的一般程序。与大约 10 分钟相比，微波辐射的应用将反应时间缩短至 10 分钟。在标准条件下进行 1,3-偶极环加成反应 48 小时。在体外评估了所有化合物对多种 DNA 和 RNA 病毒的抑制活性。没有一种化合物在亚毒性浓度下具有抗病毒活性。化合物 17k 对人 T 淋巴细胞的增殖表现出中等抑制作用（CEM 的 IC50 = 64 µM）。
• A2A ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Elzein Elfatih

  公开号：US20070208040A1

  公开（公告）日：2007-09-06

  The present invention relates to novel compounds that are A 2A adenosine receptor antagonists, and to their use in treating mammals for various disease states, such as obesity, CNS disorders, including the “movement disorders” (Parkinson's disease, Huntington's Chorea, and catelepsy), and cerebral ischemia, excitotoxicity, cognitive and physiological disorders, depression, ADHD, and drug addiction (alcohol, amphetamine, cannabinoids, cocaine, nicotine, and opioids) and to their use in the enhancement of immune response. The invention also relates to methods for the preparation of such compounds, and to pharmaceutical compositions containing them.

  本发明涉及一种新型化合物，它们是A2A腺苷受体拮抗剂，并且用于治疗哺乳动物的各种疾病状态，如肥胖、中枢神经系统紊乱，包括“运动障碍”（帕金森病、亨廷顿舞蹈症和猫病）、脑缺血、兴奋毒性、认知和生理紊乱、抑郁症、注意力缺陷多动障碍（ADHD）以及药物成瘾（酒精、安非他明、大麻素、可卡因、尼古丁和阿片类药物），以及用于增强免疫应答。该发明还涉及制备这类化合物的方法，以及含有它们的药物组合物。
• A2A adenosine receptor antagonists
  申请人：——

  公开号：US20030149060A1

  公开（公告）日：2003-08-07

  Disclosed are novel A 2A adenosine receptor antagonists, useful for treating various disease states, for example cardiovascular disorders, including tissue damage due to ischemia, CNS diseases, including Parkinson's disease, depression, and the like.

  揭示了一种新型A2A腺苷受体拮抗剂，可用于治疗各种疾病状态，例如心血管疾病，包括因缺血引起的组织损伤，中枢神经系统疾病，包括帕金森病、抑郁症等。