Basic information
- CAS
144-44-5- Standard SMILES
C[N+]1(CCCCC[N+]2(C)CCCC2)CCCC1- InChIKey
XSBSKEQEUFOSDD-UHFFFAOYSA-N- Molecular formula
- C15H32N2+2
- Average molar mass
- 240.43 g/mol
- Monoisotopic mass
- 240.25654903
Overview
Pentolinium ion is a dication whose structure comprises a pentane backbone linking two 1-methylpyrrolidinium groups; a nicotinic antagonist used as a ganglionic blocking agent in hypertension. It contains a pyrrolidinium ion.
Names & identifiers
- Preferred name
- Pentolinium
- IUPAC
- 1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-ium
- English name
- 1,1'-(Pentamethylene)bis(1-methylpyrrolidinium)
- Molecular formula
- C15H32N2+2
- Molecular weight
- 240.43
Names & synonyms
PentoliniumPentoloniumPentolonumpentolineumpentolinium ion144-44-5Pentolinium cation1-methyl-1-[5-(1-methylpyrrolidin-1-ium-1-yl)pentyl]pyrrolidin-1-iumULL76WPU5XDTXSID5048554CHEBI:3474011-methyl-1-(5-(1-methylpyrrolidin-1-ium-1-yl)pentyl)pyrrolidin-1-ium
Show more names
1,1'-Pentamethylenebis(1-methylpyrrolidinium)1,1'-(Pentamethylene)bis(1-methylpyrrolidinium)1,1'-(Pentamethylene)bis(1-methylpyrrolidine-1-ium)1,1'-(1,5-Pentanediyl)bis(1-methylpyrrolidin-1-ium)
RefChem:860063DTXCID50281101,1'-(1,5-Pentanediyl)bis(1-methylpyrrolidinium)1,1'-pentane-1,5-diylbis(1-methylpyrrolidinium)UNII-ULL76WPU5XCHEMBL1271PENTOLONIUM [WHO-DD]1,1/'-(Pentamethylene)bis(1-methylpyrrolidinium)
Database identifiers
- CAS
144-44-5、52-62-0- PubChem CID
- 5850
- DTXSID
DTXSID5048554
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 6
- Heavy atoms
- 17
- Formal charge
- 2
- Complexity
- 201
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.16e-05 g/L
Melting Point213 °C (tartrate salt)
Physical DescriptionSolid
Physicochemical properties
- FDA UNII
- 76 WPU5X · ULL76WPU5X
Chemistry & industry
Pharmacology
PharmacodynamicsPentolinium acts as a ganglionic blocking agent. Pentolinium inhibits release of adrenaline and noradrenaline from adrenergic nerves. It is used as an antihypertensive, and can be administered orally, intramuscularly, and subcutaneously.
Mechanism of Action
Pentolinium binds to the nicotinic (ganglion) acetylcholine receptor. This receptor/channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. Blockage of the receptor leads to smooth muscle relaxation and vasodilaton.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Agents having as their major action the interruption of neural transmission at nicotinic receptors on postganglionic autonomic neurons. Because their actions are so broad, including blocking of sympathetic and parasympathetic systems, their therapeutic use has been largely supplanted by more specific drugs. They may still be used in the control of blood pressure in patients with acute dissecting aortic aneurysm and for the induction of hypotension in surgery.
Drugs that bind to nicotinic cholinergic receptors (RECEPTORS, NICOTINIC) and block the actions of acetylcholine or cholinergic agonists. Nicotinic antagonists block synaptic transmission at autonomic ganglia, the skeletal neuromuscular junction, and at central nervous system nicotinic synapses.
Cellular LocationsMembrane
Additional notes
DefinitionChEBI: A dication whose structure comprises a pentane backbone linking two 1-methylpyrrolidinium groups; a nicotinic antagonist used as a ganglionic blocking agent in hypertension.
Related reactions
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Compound notes
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