Adenosine 3',5'-cyclic monophosphate 腺苷-3,5-环单磷酸

CAS 60-92-4 MFCD00005845

化学结构图

60-92-4
SMILES: Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(O)O[C@H]2[C@H]1O

化学属性

Mol. FormulaC10H12N5O6P
Mol. Weight329.21
Density2.47
Melting Point260°C
TSCAYes
Solubility50 MG/ML
Appearance powder
Boiling Point701.5°C at 760 mmHg

别名和识别编码

Chemical NameAdenosine 3',5'-cyclic monophosphate
Synonym Cyclic AMP {LY} Cyclic AMP {} {LY} Cyclic AMP {} {} {LY} Cyclic AMP {} {} {} {LY} Cyclic AMP {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cyclic AMP {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
CAS Number60-92-4
EC Number200-492-9
Beilstein Registry Number52645
MDL NumberMFCD00005845
PubChem Substance ID6076
Reaxys-RN52645
Merck Number2708
Chemical Name Translation腺苷-3,5-环单磷酸
Wiswesser Line NotationT56 BO FOPOTJ DQ GQ GO C- DT56 BN DN FN HNJ IZ
LabNetwork Molecule IDLN00191237
InChIInChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
Canonical SMILESNC1=C2N=CN([C@@H]3O[C@]4([H])COP(O)(O[C@@]4([H])[C@H]3O)=O)C2=NC=N1
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分类

  • {SNA} A-AM, Bioactive Small Molecules,
  • A-AM, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cyclic Nucleotide Metabolism, Cyclic Nucleotides and Analogs, G Proteins and Cyclic Nucleotides, Kinase/Phosphatase Biology, Protein Kinase A (PKA), Serine/Threonine Kinase Activators, Serine/Threonine Kinase Biology
  • {SNA} A-AM, Bioactive Small Molecule Alphabetical Index, Cyclic Nucleotide Metabolism, Cyclic Nucleotides and Analogs, G Proteins and Cyclic Nucleotides, Kinase/Phosphatase Biology, Protein Kinase A (PKA), Serine/Threonine Kinase Activators, Serine/Threonine Kinase Biology, 生物活性小分子, 细胞信号转导和神经科学,
  • {SNA} A-AM,

产品应用

  • cAMP依赖的蛋白激酶(PKA)的激动剂。cAMP是许多系统至神经递质或荷尔蒙诱导的受体刺激的第二信使, cAMP/PKA信号途径可以抑制细胞扩增、诱导分化和导致细胞凋亡。

相关文献及参考

  • Chen, T.C., et al., Up-regulation of the cAMP/PKA pathway inhibits proliferation, induces differentiation, and leads to apoptosis in malignant gliomas. Lab. Invest. 78 , 165-174, (1998) 摘要
  • Daniel, P.B., et al., Cyclic AMP signaling and gene regulation. Annu. Rev. Nutr. 18 , 353-383, (1998)
  • Merck 14 ,2708
  • Merck: 14,2708
  • Merck: 14,2708 Beilstein: 26,IV,3618
  • [1]. Cook SJ, et al. Inhibition by cAMP of Ras-dependent activation of Raf. Science. 1993 Nov 12;262(5136):1069-72.

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘;
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触;
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后,立即用大量水冲洗并征求医生意见;
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护;
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时,立即求医(可能时出示标签);
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R34 Causes burns 会导致灼伤
Precautionary statements
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
RTECSAU7357600
Storage condition -20°C {LY} -20°C 2-8°C 2-8°C, protect from light <0°C <;0 {} {LY} -20°C {} {} {LY} -20°C {} {} {} {LY} -20°C {} {} {} {} {LY} -20°C {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} -20°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY}
Hazard Codes C,Xi C
TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 100 umol/L
REFERENCE :
   JIDEAE Journal of Investigative Dermatology.  (Williams & Wilkins Co., 428
   E. Preston St., Baltimore, MD 21202)  V.1-    1938- Volume(issue)/page/year:
   65,52,1975

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Fibroblast
DOSE/DURATION           : 500 umol/L
REFERENCE :
   IJCNAW International Journal of Cancer.  (International Union Against
   Cancer, 3 rue du Conseil- General, 1205 Geneva, Switzerland)  V.1-    1966-
   Volume(issue)/page/year: 13,404,1974

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - rat Cells - not otherwise specified
DOSE/DURATION           : 10 mmol/L
REFERENCE :
   CYTBAI Cytobios. (Faculty Press, 88 Regent St., Cambridge, UK)  V.1- 1969- 
   Volume(issue)/page/year: 4,121,1971

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - rat Liver
DOSE/DURATION           : 10 mmol/L
REFERENCE :
   CYTBAI Cytobios. (Faculty Press, 88 Regent St., Cambridge, UK)  V.1- 1969- 
   Volume(issue)/page/year: 4,121,1971

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - rat Cells - not otherwise specified
DOSE/DURATION           : 10 mmol/L
REFERENCE :
   CYTBAI Cytobios. (Faculty Press, 88 Regent St., Cambridge, UK)  V.1- 1969- 
   Volume(issue)/page/year: 4,121,1971

其他信息

  • MOL 文件:60-92-4.mol
  • 用途:用于缓解心绞痛及急、慢性心肌梗塞等病症
  • 水中溶解度:50mg/mL。
  • NIST化学物质信息:Adenosine 3',5'-cyclic monophosphate(60-92-4)
  • RTECS号:AU7357600
  • EPA化学物质信息:Adenosine, cyclic 3',5'-(hydrogen phosphate)(60-92-4)
  • 图谱信息:腺苷环磷酸酯(60-92-4)质谱(MS) 腺苷环磷酸酯(60-92-4)红外图谱(IR2) 腺苷环磷酸酯(60-92-4)红外图谱(IR1)
  • color:white
  • F:10-21
  • 比旋光度:-53.7 ° (c=0.7,water)
  • 生产方法:以5'-AMP为原料 5'-AMP复盐的制备 投料比为N,N'-二环已基吗林胍(m):吡啶(V):5'-AMP(m):水(V)=1:9.62:1.19:1.7。将N,N'-二环己基吗啉胍及吡啶加入反应器中,加热至80℃溶解,再加5'-AMP和水,5'-AMP溶解后,在80℃减压蒸馏至干,加少量无水吡啶,减压蒸干,反复两次,得产品。 5'-AMP[N,N'-二环己基吗啉胍,吡啶]→[80℃]5'-AMP复盐 cAMP粗品的制备 投料比为5'-AMP复盐(m):无水吡啶(V):二环己基碳二亚胺(V)=1:235:1.07。先将二分之一量的无水吡啶与二环已基碳二亚胺混合,在140-145℃下回流,在回流下将5'-AMP复盐与另二分之一量的无水吡啶混合溶液分批缓慢加入,约在3h内加完,加完后继续回流6h,冷却, 70℃减压蒸出吡啶至干,残留物用乙醚和水的混合液(1:1.5)溶解,过滤除去不溶物二环己脲,将滤液中的水层分出,再用乙醚洗三次,用水泵抽去残留的乙醚。 5'-AMP复盐[无水吡啶,二环己基碳二亚胺]→[9h]cAMP粗品 cAMP粗品的精制 将水层用盐酸调pH为2,过滤除去不溶物,滤液用100目的强碱性苯乙烯系阳离子交换树脂001×7(732)吸附,树脂用量为5'-AMP的80-100倍。然后用1.01mol/L盐酸洗脱,收集第二吸收峰(E260),用碳酸氢铵中和至中性,60℃减压浓缩至cAMP含量为15%-20%为止,过滤,滤液加等体积的乙醇(95%)后,用2mol/L盐酸调pH为2,过滤,干燥,得cAMP成品。 cAMP粗品[001×7(732)树脂,盐酸,乙醇]→[pH2]cAMP成品。
  • 腺苷环磷酸酯价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 225805000 腺苷环磷酸酯 Adenosine 3',5'-cyclic monophosphate 99+% 500 MG 1378元 2010/06/21 225800010 腺苷环磷酸酯 Adenosine 3',5'-cyclic monophosphate 99+% 1 GR 2154元 2010/06/21 225800050 腺苷环磷酸酯 Adenosine 3',5'-cyclic monophosphate 99+% 5 GR 7434元

系列性分类


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