ChemicalBook > CAS DataBase List > EHNA HYDROCHLORIDE

EHNA HYDROCHLORIDE

Product Name
EHNA HYDROCHLORIDE
CAS No.
51350-19-7
Chemical Name
EHNA HYDROCHLORIDE
Synonyms
EHNA;EHNA HCL;NSC-263165;MEP1 HYDROCHLORIDE;EHNA HYDROCHLORIDE;9-erythro-(2-Hydroxyl-3-nonyl)adenine;(+)-erythro-9-(2-Hydroxy-3-nonyl)adenine;ERYTHRO-9-(2-HYDROXY-3-NONYL)ADENINE, HCL;ERYTHRO-9-(2-HYDROXY-3-NONYL)ADENINE HYDROCHLORIDE;9-erythro-(2-Hydroxy-3-nonyl)-adenine hydrochloride
CBNumber
CB1233267
Molecular Formula
C14H23N5O
Formula Weight
277.37
MOL File
51350-19-7.mol
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EHNA HYDROCHLORIDE Property

Melting point:
183~184℃
storage temp. 
0-6°C
solubility 
DMSO: 12 mg/mL
form 
solid
color 
white
Water Solubility 
water: 25mg/mL
Stability:
Stable for 2 years as supplied. Solutions in distilled water may be stored at -20°C for up to 3 months.
CAS DataBase Reference
51350-19-7
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Safety

WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
324630
Product name
EHNA, Hydrochloride - CAS 51350-19-7 - Calbiochem
Packaging
10mg
Price
$102
Updated
2025/07/31
Tocris
Product number
1261
Product name
EHNA hydrochloride
Purity
≥98%(HPLC)
Packaging
50
Price
$389
Updated
2021/12/16
Tocris
Product number
1261
Product name
EHNA hydrochloride
Purity
≥98%(HPLC)
Packaging
10
Price
$97
Updated
2021/12/16
TRC
Product number
H825590
Product name
9-Erythro-(2-Hydroxyl-3-nonyl)adenine
Packaging
25mg
Price
$120
Updated
2021/12/16
Usbiological
Product number
366880
Product name
EHNA Hydrochloride
Packaging
25mg
Price
$336
Updated
2021/12/16
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EHNA HYDROCHLORIDE Chemical Properties,Usage,Production

Description

EHNA (51350-19-7) inhibits phosphodiesterase 2 (PDE2) (IC50 = 0.8 – 5.5 μM in a variety of tissues and species) over PDE1, PDE3, or PDE4 (IC50 values > 100 μM).1,2 It also inhibits adenosine deaminase (ADA), IC50 = 1.2 and 1.5 μM in human RBCs and astrocytoma cells, respectively3, which may be responsible for its ability to induce apoptosis in malignant pleural mesothelioma cell lines4. Because it blocks breakdown of adenosine to inosine and hypoxanthine, EHNA prevents formation of free radical substrates, protecting against cardiac reperfusion-mediated injury.5 It inhibits differentiation and maintains expression of pluripotency markers in hESCs, but not through inhibition of PDEs or ADA.6

Chemical Properties

White Solid

Uses

A potent inhibitor of phosphodiesterase II (PDE II) (IC50=800nM). Does ot inhibit other PDE isozymes (IC50>100uM). Inhibits the retrograde transport motor, dynein. Also inhibits adenosine deaminase (Ki=4nM)

Uses

9-erythro-(2-Hydroxyl-3-nonyl)adenine is an intermediate in the synthesis of potent inhibitor of phosphodiesterase II.

Definition

ChEBI: (2R,3S)-EHNA is eHNA of absolute configuration 2R,3S. Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase. It has a role as an EC 3.5.4.4 (adenosine deaminase) inhibitor and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor. It is a conjugate base of a (2R,3S)-EHNA(1+). It is an enantiomer of a (2S,3R)-EHNA.

Biological Activity

Selective inhibitor of cGMP-stimulated phosphodiesterase (PDE2) (IC 50 = 0.8 - 4 mM). Also a potent inhibitor of adenosine deaminase.

References

[1] THOMAS PODZUWEIT  Antje M  Peter Nennstiel. Isozyme selective inhibition of cGMP-stimulated cyclic nucleotide phosphodiesterases by erythro-9-(2-hydroxy-3-nonyl) adenine[J]. Cellular signalling, 1995, 7 7: Pages 733-738. DOI:10.1016/0898-6568(95)00042-n
[2] P F MÉRY. Erythro-9-(2-hydroxy-3-nonyl)adenine inhibits cyclic GMP-stimulated phosphodiesterase in isolated cardiac myocytes.[J]. Molecular Pharmacology, 1995, 48 1: 121-130.
[3] J BARANKIEWICZ. Regulation of adenosine concentration and cytoprotective effects of novel reversible adenosine deaminase inhibitors.[J]. Journal of Pharmacology and Experimental Therapeutics, 1997, 283 3: 1230-1238.
[4] YASUHIRO NAKAJIMA. Adenosine deaminase inhibitor EHNA exhibits a potent anticancer effect against malignant pleural mesothelioma.[J]. Cellular Physiology and Biochemistry, 2015: 51-60. DOI:10.1159/000369674
[5] ANWAR S. ABD-ELFATTAH PH.D.  Andrew S W M D. Separation Between Ischemic and Reperfusion Injury by Site Specific Entrapment of Endogenous Adenosine and Inosine Using NBMPR and EHNA[J]. Journal of Cardiac Surgery, 1994, 9 3S: 387-396. DOI:10.1111/jocs.1994.9.3s.387
[6] PETER BURTON. Erythro-9-(2-hydroxy-3-nonyl)adenine (EHNA) blocks differentiation and maintains the expression of pluripotency markers in human embryonic stem cells.[J]. Biochemical Journal, 2010, 432 3: 575-584. DOI:10.1042/bj20100726

EHNA HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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EHNA HYDROCHLORIDE Suppliers

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51350-19-7, EHNA HYDROCHLORIDERelated Search:


  • 9-ERYTHRO-(2-HYDROXY-3-N-NONYL) ADENINE HYDROCHLORIDE
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  • 51350-19-7
  • C14H23N5OHCl
  • C14H24ClN5O
  • Adenosine deaminase inhibitor.
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