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C1055

Sigma-Aldrich

Cromakalim

Synonym(s):

(±)-trans-6-Cyano-3,4-dihydro-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-2H-1-benzopyran-3-ol

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About This Item

Empirical Formula (Hill Notation):
C16H18N2O3
CAS Number:
Molecular Weight:
286.33
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

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

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.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  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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    Ask a Scientist here.

W Spinelli et al.
European journal of pharmacology, 179(3), 243-252 (1990-04-25)
The cardiac electrophysiologic effects of the potassium channel activators cromakalim, pinacidil and nicorandil were determined in anesthetized open-chest normotensive dogs using conventional surface electrogram recording techniques. Intravenous administration of cromakalim (0.025-0.5 mg/kg), pinacidil (0.1-2.0 mg/kg) and nicorandil (0.1-2.5 mg/kg) produced
BRL 34915 (cromakalim) activates ATP-sensitive K+ current in cardiac muscle
Sanguinetti M C, et al.
Proceedings of the National Academy of Sciences, 85(21), 8360-8364 (1988)
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
E Grana et al.
European journal of pharmacology, 319(1), 57-64 (1997-01-14)
The present study was carried out to look at the influence of the K+ channel opener cromakalim, compared with suramin and prazosin, on the contractile response evoked by single-pulse field stimulation and exogenous agonists in epididymal and prostatic portions of
Cromakalim blocks the purinergic response evoked in rat vas deferens by single-pulse electrical stimulation
Grana E, et al.
European Journal of Pharmacology, 319(1), 57-64 (1997)

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