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C1055

Sigma-Aldrich

Cromakalim

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Synonym(s):
(±)-trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol
Empirical Formula (Hill Notation):
C16H18N2O3
CAS Number:
94470-67-4
Molecular Weight:
286.33
MDL number:
MFCD00133201
PubChem Substance ID:
24891962
NACRES:
NA.77

form

powder

Quality Level

200

storage temp.

2-8°C

SMILES string

CC1(C)Oc2ccc(cc2[C@H]([C@@H]1O)N3CCCC3=O)C#N

InChI

1S/C16H18N2O3/c1-16(2)15(20)14(18-7-3-4-13(18)19)11-8-10(9-17)5-6-12(11)21-16/h5-6,8,14-15,20H,3-4,7H2,1-2H3/t14-,15+/m1/s1

InChI key

TVZCRIROJQEVOT-CABCVRRESA-N

Gene Information

rat ... Kcna1(24520) , Kcnj1(24521) , Kcnj5(29713) , Kcnj8(25472)

Application

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.

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.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  6. Can I dissolve Product C1055, Cromakalim, in something else besides chloroform? 

    Yes. One publication reports that Product C1055, Cromakalim, can be dissolved in DMSO at 20 mM.  Post, J.M., et al., Effect of cromakalim and lemakalim on slow waves and membrane currents in colonic smooth muscle.  Am. J. Physiol. Cell. Physiol.,  260(2), C375-C382 (1991).

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I Cavero et al.
The Journal of pharmacology and experimental therapeutics, 248(3), 1261-1268 (1989-03-01)
Cromakalim (BRL 34915), a K+ channel activator, and diltiazem relaxed isolated rat aortic rings contracted with a low KCl concentration (25 mM). Gilbenclamide (0.1-3 microM) did not modify base-line resting tension or responses to KCl but prevented the vasorelaxant effects
Effect of cromakalim on the purinergic and cholinergic transmission in the rat detrusor muscle
Boselli C, et al.
European Journal of Pharmacology, 335(1), 23-30 (1997)
Xue-Feng Wu et al.
Pain, 152(11), 2605-2615 (2011-09-13)
Adenosine triphosphate-sensitive potassium (K(ATP)) channels are suggested to be involved in pathogenesis of neuropathic pain, but remain underinvestigated in primary afferents and in the spinal cord. We examined alterations of K(ATP) channels in rat spinal cord and tested whether and
P Lijnen et al.
European journal of clinical pharmacology, 37(6), 609-611 (1989-01-01)
The effect of cromakalim, a K(+)-channel activator, on the plasma renin-angiotensin-aldosterone system, catecholamines and alpha-atrial natriuretic peptide, and on the intraerythrocyte concentration and transmembrane fluxes of Na+ and K+ has been investigated in 18 normal male subjects, in a double-blind
Xavier Florence et al.
Bioorganic & medicinal chemistry, 19(13), 3919-3928 (2011-06-15)
The synthesis of different series of 4- and 6-substituted R/S-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans is described. All of these new benzopyran derivatives were bearing, at the 4-position, a phenylthiourea moiety substituted on the phenyl ring by a meta or a para-electron-withdrawing group such as
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