Pinacidil

Last updated
Pinacidil
Pinacidil structure.svg
Names
IUPAC name
N-cyano-N'-pyridin-4-yl-N''-(1,2,2-trimethylpropyl)guanidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.056.614 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C13H19N5/c1-10(13(2,3)4)17-12(16-9-14)18-11-5-7-15-8-6-11/h5-8,10H,1-4H3,(H2,15,16,17,18) X mark.svgN
    Key: IVVNZDGDKPTYHK-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C13H19N5/c1-10(13(2,3)4)17-12(16-9-14)18-11-5-7-15-8-6-11/h5-8,10H,1-4H3,(H2,15,16,17,18)
    Key: IVVNZDGDKPTYHK-UHFFFAOYAY
  • CC(C(C)(C)C)N=C(NC#N)NC1=CC=NC=C1
Properties
C13H19N5
Molar mass 245.32346
Pharmacology
C02DG01 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pinacidil is a cyanoguanidine drug that opens ATP-sensitive potassium channels producing peripheral vasodilatation of arterioles. [1] It reduces blood pressure and peripheral resistance and produces fluid retention. [2]

Contents

Synthesis

Thieme Synthesis: Patents: Pinacidil synthesis.svg
Thieme Synthesis: Patents:

Condensation of 4-isothiocyanotopyridine [76105-84-5] (1) and 3,3-dimethyl-2-butanamine [3850-30-4] (2) gives thiourea [67027-06-9] (3). Treatment of that intermediate with a mixture of triphenylphosphine, carbon tetrachloride, and triethylamine leads to the unsymmetrical carbodiimide, CID:20501933 (4'). Addition of cyanamid affords pinacidil (5).

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References

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  2. Reynolds, James Blair; Martindale, William L. (1996). The extra pharmacopoeia (31st ed.). London: Royal Pharmaceutical Society. pp.  2739 pages. ISBN   0-85369-342-0.
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  4. Hansen, E. T.; Petersen, H. J. (2006). "Synthesis ofN-Alkyl-N'-cyano-N″-4-pyridylguanidines from 4-Pyridyldithiocarbamic AcidviaN-Alkyl-N′-4-Pyridylthioureas, orvia4-Pyridylcyaniminothiocarbamic Acid". Synthetic Communications. 14 (13): 1275–1283. doi:10.1080/00397918408076809.
  5. Zhang, Hao; Liu, Rui-Quan; Liu, Ke-Chang; Li, Qi-Bo; Li, Qing-Yang; Liu, Shang-Zhong (2014). "A One-Pot Approach to Pyridyl Isothiocyanates from Amines". Molecules 19(9): 13631–13642. doi:10.3390/molecules190913631.
  6. Hans J. Petersen, USRE31244E (1983 to Leo Pharma AS).
  7. Hans Jorgen Petersen, U.S. Patent 4,057,636 (1977 to Leo Pharma AS).