| Identification | Back Directory | [Name]
N6-CYCLOHEXYLADENOSINE | [CAS]
36396-99-3 | [Synonyms]
CHA
Cyclohexyladenosine
N-Cyclohexyladenosine
N6-CYCLOHEXYLADENOSINE
Adenosine, N-cyclohexyl-
N6-Cyclohexyladenosine,CHA
N(sup 6)-cyclohexyladenosine
(2R,4S)-4-fluoropyrrolidine-6-carboxylicacid
N6-CYCLOHEXYLADENOSINE (CHA) SELECTIVE A 1 ADENOSIN
(2R,3R,4S,5R)-2-(6-(CyclohexylaMino)-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol | [Molecular Formula]
C16H23N5O4 | [MDL Number]
MFCD00036808 | [MOL File]
36396-99-3.mol | [Molecular Weight]
349.38 |
| Chemical Properties | Back Directory | [Melting point ]
182 - 184°C | [Boiling point ]
675.2±65.0 °C(Predicted) | [density ]
1.71±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.12±0.70(Predicted) | [color ]
White to Off-White | [Stability:]
Hygroscopic | [InChI]
1S/C16H23N5O4/c22-6-10-12(23)13(24)16(25-10)21-8-19-11-14(17-7-18-15(11)21)20-9-4-2-1-3-5-9/h7-10,12-13,16,22-24H,1-6H2,(H,17,18,20)/t10-,12-,13-,16-/m1/s1 | [InChIKey]
SZBULDQSDUXAPJ-XNIJJKJLSA-N | [SMILES]
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCCC4)ncnc23 |
| Hazard Information | Back Directory | [Description]
N6-Cyclohexyladenosine is an adenosine receptor agonist. It selectively binds to adenosine A1 receptors in rat cortical membranes (IC50 = 2.3 nM) over A2 receptors in rat striatal membranes (IC50 = 870 nM). N6-Cyclohexyladenosine decreases heart rate and increases coronary flow in a perfused working rat heart model ex vivo (EC25s = 5 and 860 nM, respectively). In vivo, it decreases heart rate and blood pressure in normotensive rats (EC25s = 2.4 and 4.2 μg/kg, respectively). N6-Cyclohexyladenosine (100 μM) induces sleep in rats when administered via basal forebrain infusion. N6-Cyclohexyladenosine also decreases locomotor activity in mice (ED50 = 60 μg/kg, i.p.). | [Uses]
N6-Cyclohexyladenosine is a derivative of Adenosine (A280400), and is used testing adenosine A1 and A2A receptor activation for pharmaceuticals such as antidepressants. N6-Cyclohexyladenosine also is used as a JAK2 inhibitor, blocking STAT3 signalling in human cancer cells. | [Biochem/physiol Actions]
Selective A1 adenosine receptor agonist. | [storage]
Store at -20°C | [References]
[1] A J HUTCHISON. CGS 21680C, an A2 selective adenosine receptor agonist with preferential hypotensive activity.[J]. Journal of Pharmacology and Experimental Therapeutics, 1989, 251 1: 47-55.
[2] CARLOS BLANCO-CENTURION. Adenosine and sleep homeostasis in the Basal forebrain.[J]. Journal of Neuroscience, 2006, 26 31: 8092-8100. DOI: 10.1523/jneurosci.2181-06.2006
[3] OLGA NIKODIJEVI? Kenneth A J John W Daly. Characterization of the locomotor depression produced by an A2-selective adenosine agonist[J]. FEBS Letters, 1990, 261 1: Pages 67-70. DOI: 10.1016/0014-5793(90)80638-y |
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