A dual inhibitor of PDE2 and ADA
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EHNA (hydrochloride)

Item No. 13352

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αR,βS)-rel-6-amino-β-hexyl-α-methyl-9H-purine-9-ethanol, monohydrochloride
CAS Number
58337-38-5
Synonyms
  • NSC 263164
  • erythro-9-(2-Hydroxy-3-nonyl)adenine
Molecular Formula
C14H23N5O • HCl
Formula Weight
313.8
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/mlWater: 10 mg/ml
λmax
210, 261 nm
SMILES
NC1=C2C(N([C@@H](CCCCCC)[C@H](O)C)C=N2)=NC=N1.Cl
InChi Code
InChI=1S/C14H23N5O.ClH/c1-3-4-5-6-7-11(10(2)20)19-9-18-12-13(15)16-8-17-14(12)19;/h8-11,20H,3-7H2,1-2H3,(H2,15,16,17);1H/t10-,11+;/m1./s1
InChi Key
VVDXNJRUNJMYOZ-DHXVBOOMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $43

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    10 mg

    $82

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    25 mg

    $194

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    Product Description

    EHNA is a reversible adenosine deaminase inhibitor (IC50 = 1.2 μM in human red blood cells) that also selectively inhibits the cGMP-specific phosphodiesterase (PDE2) (IC50s = 0.8 and 2 μM from human and porcine myocardium, respectively, 3.5 μM in rat hepatocyte, and 5.5 μM in human platelet).1,2 Comparatively, EHNA is much less potent at inhibiting PDE1, PDE3, or PDE4 (IC50s > 100 μM).1 EHNA has been used to evaluate cardioprotective and neuroprotective effects during ischemia, to study the role of cAMP/cGMP signaling, and to maintain pluripotency/prevent differentiation of human embryonic stem cells.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Podzuweit, T., Nennstiel, P., and Müller, A. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine. Cell. Signal. 7(7), 733-738 (1995).

    2. Michie, A.M., Lobban, M., Müller, T., et al. Rapid regulation of PDE-2 and PDE-4 cyclic AMP phosphodiesterase activity following ligation of the T cell antigen receptor on thymocytes: Analysis using the selective inhibitors erythro-9-(2-hydroxy-3-nonyl)-adenine (EHNA) and rolipram. Cell. Signal. 8(2), 97-110 (1996).

    3. Barankiewicz, J., Danks, A.M., Abushanab, E., et al. Regulation of adenosine concentration and cytoprotective effects of novel reversible adenosine deaminase inhibitors. J. Pharmacol. Exp. Ther. 283(3), 1230-1238 (1997).

    4. Dickinson, N.T., Jang, E.K., and Haslam, R.J. Activation of cGMP-stimulated phosphodiesterase by nitroprusside limits cAMP accumulation in human platelets: Effects on platelet aggregation. Biochem. J. 323(Pt. 2), 371-377 (1997).

    5. Burton, P., Adams, D.R., Abraham, A., et al. Erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) blocks differentiation and maintains the expression of pluripotency markers in human embryonic stem cells. Biochem. J. 432(3), 575-584 (2010).