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CROMAKALIM

Product Name
CROMAKALIM
CAS No.
94470-67-4
Chemical Name
CROMAKALIM
Synonyms
BRL-34915;CROMAKALIM;AKOS 91890;(±)-Cromakalim;(+/-)-CROMAKALIM;Cromakalim, KIR6.x (KATP) channel activator;Cromakalim=([+/-]-trans-6-Cyano-3,4-dihydro-2,2-;rac-(3α*,4β*)-3-Hydroxy-2,2-dimethyl-4-(2-oxopyrrolidine-1-yl)chroman-6-carbonitrile;(-trans-6-Cyano-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-3,4-dihydro-2H-benzo[b]pyran-3-ol;(3S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydrochromene-6-carbonitrile
CBNumber
CB7771686
Molecular Formula
C16H18N2O3
Formula Weight
286.33
MOL File
94470-67-4.mol
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CROMAKALIM Property

Melting point:
242-244°C
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
form 
solid
color 
Off-white
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C1055
Product name
Cromakalim
Packaging
10mg
Price
$218
Updated
2025/07/31
Sigma-Aldrich
Product number
C1055
Product name
Cromakalim
Packaging
50mg
Price
$966
Updated
2025/07/31
Cayman Chemical
Product number
14601
Product name
(±)-Cromakalim
Purity
≥99%
Packaging
10mg
Price
$121
Updated
2024/03/01
Cayman Chemical
Product number
14601
Product name
(±)-Cromakalim
Purity
≥99%
Packaging
50mg
Price
$481
Updated
2024/03/01
Tocris
Product number
1377
Product name
Cromakalim
Purity
≥99%(HPLC)
Packaging
10
Price
$205
Updated
2021/12/16
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CROMAKALIM Chemical Properties,Usage,Production

Description

(±)-Cromakalim is a prototypical activator of the ATP-sensitive potassium channel, SUR2-Kir6, that displays anti-ischemic (EC25 = 8.9 μM) and cardioprotective (IC50 = 0.03 μM) effects in rat hearts. (±)-Cromakalim has also been shown to relax bladder smooth muscle in vitro. It has been used to investigate potassium channel biology and as a scaffold to develop increasingly selective K+ channel openers with clinical relevance.

Chemical Properties

White Crystalline Solid

Uses

Cromakalim has been used:

  • as a potassium channel agonist to study its response to an acute increase in downstream pressure in rat lymphatic vessels.
  • as a potassium channel opener to study its effects on the release of transmitters from adrenergic nerves in rat vas deferens.
  • as a potassium channel activator to study its effects on the release of transmitters from purinergic and cholinergic nerves in the rat detrusor muscle.

Uses

Cromakalim causes vasodilation by activation of potassim channels

Definition

ChEBI: Cromakalim is a 1-benzopyran.

Biological Activity

Prototypical K ATP channel opener. Relaxes rabbit isolated portal vein with an IC 50 value of 21 nM . Potent, orally active and hypotensive in vivo .

Biochem/physiol Actions

Cromakalim is an activator of the potassium channel. It is involved in the relaxation of the vascular smooth muscles. Cromakalim exhibits anti-hypertensive activity.

References

[1] M C SANGUINETTI. BRL 34915 (cromakalim) activates ATP-sensitive K+ current in cardiac muscle.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1988, 85 21: 8360-8364. DOI:10.1073/pnas.85.21.8360
[2] XUE-FENG WU . Reopening of ATP-sensitive potassium channels reduces neuropathic pain and regulates astroglial gap junctions in the rat spinal cord[J]. PAIN®, 2011, 152 11: Pages 2605-2615. DOI:10.1016/j.pain.2011.08.003
[3] PHILIPPE TRECHOT  Fanny T  Jean Baptiste Conart. ATP sensitive potassium channel openers: A new class of ocular hypotensive agents[J]. Experimental eye research, 2019, 178: Pages 223-224. DOI:10.1016/j.exer.2016.06.014
[4] ZHIJUAN CAO. Opening of the Adenosine Triphosphate-sensitive Potassium Channel Attenuates Morphine Tolerance by Inhibiting JNK and Astrocyte Activation in the Spinal Cord[J]. Clinical Journal of Pain, 2016, 32 1: 617-623. DOI:10.1097/ajp.0000000000000299

CROMAKALIM Preparation Products And Raw materials

Raw materials

Preparation Products

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CROMAKALIM Suppliers

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94470-67-4, CROMAKALIMRelated Search:

3-M-TOLYL-DL-BETA-ALANINOL (S)-3-(1-Aminoethyl)benzonitrile 3-(methylaminomethyl)benzonitrile Anisonitrile 4-ETHOXYBENZONITRILE 4-TERT-BUTOXYBENZONITRILE (R)-3-(1-aminoethyl)benzonitrile (S)-3-Amino-3-phenylpropan-1-ol LEVCROMAKALIM (S)-1-(2-Methoxyphenyl)ethylamine 3-CYANOBENZYLAMINE CROMAKALIM CHROMAN-4-YLAMINE (S)-3-Dimethylamino-3-phenylpropanol 3-(Diethylamino)-1,2-propanediol N-(2-Hydroxyethyl)-2-pyrrolidone 1-(3-HYDROXYPROPYL)-2-PYRROLIDONE 4-isopropoxybenzonitrile

  • Cromakalim=([+/-]-trans-6-Cyano-3,4-dihydro-2,2-
  • (+/-)-CROMAKALIM
  • CROMAKALIM
  • TRANS-3,4-DIHYDRO-3-HYDROXY-2,2-DIMETHYL-4-(2-OXO-1-PYRROLIDINYL)-2H-1-BENZOPYRAN-6-CARBONITRILE
  • (+/-)-TRANS-6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-4-(2-OXOPYRROLIDIN-1-YL)-2H-1-BENZOPYRAN-3-OL
  • [+/-]-TRANS-6-CYANO-3,4-DIHYDRO-2,2-DIMETHYL-4-[2-OXOPYRROLIDIN-1-YL]-2H-1-BENZOPYRAN-3-OL
  • BRL-34915
  • rac-(3α*,4β*)-3,4-Dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidine-1-yl)-2H-1-benzopyran-6-carbonitrile
  • rac-(3α*,4β*)-3-Hydroxy-2,2-dimethyl-4-(2-oxopyrrolidine-1-yl)chroman-6-carbonitrile
  • rac-3,4-Dihydro-3α*-hydroxy-2,2-dimethyl-4β*-(2-oxopyrrolidine-1-yl)-2H-1-benzopyran-6-carbonitrile
  • (3R,4S)-rel-3,4-Dihydro-3-hydroxy-2,2-diMethyl-4-(2-oxo-1-pyrrolidinyl)-2H-1-benzopyran-6-carbonitrile
  • (-trans-6-Cyano-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-3,4-dihydro-2H-benzo[b]pyran-3-ol
  • AKOS 91890
  • 2H-1-Benzopyran-6-carbonitrile, 3,4-dihydro-3-hydroxy-2,2-dimethyl-4-(2-oxo-1-pyrrolidinyl)-, (3R,4S)-rel-
  • (3S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydrochromene-6-carbonitrile
  • Cromakalim, KIR6.x (KATP) channel activator
  • (±)-Cromakalim
  • 94470-67-4
  • Monovalent Ion Channels
  • Ion Channels
  • Voltage-gated Ion Channels
  • Potassium Channel Modulators
  • BioChemical
  • Cell Biology
  • Cell Signaling and Neuroscience
  • All Inhibitors
  • Inhibitors