Basic information
- CAS
94470-67-4- Standard SMILES
CC1(C)Oc2ccc(C#N)cc2[C@H](N2CCCC2=O)[C@H]1O- InChIKey
TVZCRIROJQEVOT-LSDHHAIUSA-N- Molecular formula
- C16H18N2O3
- Average molar mass
- 286.33 g/mol
- Monoisotopic mass
- 286.13174244
Overview
See also: Cromakalim (annotation moved to).
Names & identifiers
- Preferred name
- (+)-Cromakalim
- IUPAC
- (3R,4S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydrochromene-6-carbonitrile
- English name
- CROMAKALIM
- Molecular formula
- C16H18N2O3
- Molecular weight
- 286.33
Names & synonyms
(+)-CromakalimDTXSID30131735094535-51-0RefChem:1048936DTXCID501747167CromakalinCHEMBL11684(+/-)-cromakalim(3R,4S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydro-2H-1-benzopyran-6-carbonitrile(3R,4S)-3-hydroxy-2,2-dimethyl-4-(2-oxopyrrolidin-1-yl)-3,4-dihydrochromene-6-carbonitrileNCGC00025132-01NCGC00025132-02
Show more names
BRL-34915CROMAKALIMAKOS 91890(±)-CromakalimCromakalim, KIR6.x (KATP) channel activatorCromakalim=([+/-]-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
Tocris-1377Tocris-1378SCHEMBL12833orb17050383-Hydroxy-2,2-dimethyl-4-(2-oxo-pyrrolidin-1-yl)-chroman-6-carbonitrile(3S,4R)-3-Hydroxy-2,2-dimethyl-4-(2-oxo-pyrrolidin-1-yl)-chroman-6-carbonitrileDTXSID001017959BDBM50044253
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 73.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 481
Physicochemical properties
- Melting point
- 242 · 242-244°C
- Boiling point
- 482.34 · 482.340±45.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.313 · 1.313±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in DMSO (up to 40 mg/ml) or in Ethanol (up to 10 mg/ml).
- form
- solid
- pka
- 13.175 · 13.175±0.60(predicted)
- color
- Off-white
- Stability
- 2 years · 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.
- 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
- InChIKey
- TVZCRIROJQEVOT-CABCVRRESA-N
- SMILES
- CC1(C)Oc2ccc(cc2[C@H]([C@@H]1O)N3CCCC3=O)C#N
- FDA UNII
- 0 G4X367WA3 · 0G4X367WA3
- UNSPSC Code
- 12352200 · 12352200
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
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.
UsesCromakalim 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.
UsesCromakalim causes vasodilation by activation of potassim channels
Suppliers21 total
Aladdin Scientific[email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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