Hexamethonium

A nicotinic cholinergic antagonist often referred to as the prototypical ganglionic blocker. It is poorly absorbed from the gastrointestinal tract and does not cross the blood-brain barrier. It has been used for a variety of therapeutic purposes including hypertension but, like the other ganglionic blockers, it has been replaced by more specific drugs for most purposes, although it is widely used a research tool

General

Type : Bisquaternary,Nicotinic antagonist,Trimethylammonium

Chemical_Nomenclature : 1,6-bis(trimethylammonium)hexane

Canonical SMILES : C[N+](C)(C)CCCCCC[N+](C)(C)C.[OH-].[OH-]

InChI : InChI=1S\/C12H30N2.2H2O\/c1-13(2,3)11-9-7-8-10-12-14(4,5)6\;\;\/h7-12H2,1-6H3\;2*1H2\/q+2\;\;\/p-2

InChIKey : GYLUMIIRFKDCKI-UHFFFAOYSA-L

Other name(s) : UNII-RVL393940Z,Hexamethonium hydroxide solution,Hexamethonum,Bistrium,Depressin,Hexanium


MW : 273.29

Formula : C12H30N2Cl2

CAS_number : 60-25-3

PubChem : 6059

UniChem : GYLUMIIRFKDCKI-UHFFFAOYSA-L

IUPHAR :

Wikipedia : Hexamethonium

Target

Families : Hexamethonium ligand of proteins in family: ACHE

Stucture :

Protein :

References (30)

Title : Subchronic effects following a single sarin exposure on blood-brain and blood-testes barrier permeability, acetylcholinesterase, and acetylcholine receptors in the central nervous system of rat: a dose-response study - Jones_2000_J.Toxicol.Environ.Health.A_61_695
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Abstract : Jones_2000_J.Toxicol.Environ.Health.A_61_695
ESTHER : Jones_2000_J.Toxicol.Environ.Health.A_61_695
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Title : Indian red scorpion venom modulates spontaneous activity of rat right atria through the involvement of cholinergic and adrenergic systems - Alex_1999_Indian.J.Exp.Biol_37_455
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Title : Increased plasma cholinesterase activity and mivacurium resistance: report of a family -
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Ref : Anesthesia & Analgesia , 89 :1579 , 1999
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Title : Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase - Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97
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Abstract : Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97
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Title : Pharmacology of neurotransmission to the smooth muscle of the rat and the guinea-pig prostate glands - Lau_1998_J.Auton.Pharmacol_18_349
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Title : Basal acetylcholine release in leech ganglia depolarizes neurons through receptors with a nicotinic binding site - Marin Burgin_1998_J.Exp.Biol_201_1907
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Title : Cholinergic nerve function in monkey ciliary arteries innervated by nitroxidergic nerve - Toda_1998_Am.J.Physiol_274_H1582
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Title : Evaluation of the nature of camel retinal acetylcholinesterase: inhibition by hexamethonium - Alhomida_1997_J.Enzyme.Inhib_12_303
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Title : Is the input to a GABAergic or cholinergic synapse the sole asymmetry in rabbit's retinal directional selectivity? - Grzymacz_1997_Visual.Neurosci_14_39
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Title : Possible nicotinic receptor-mediated modulation of synaptic transmission in nucleus of the solitary tract - Shiraki_1997_Am.J.Physiol_272_R869
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Title : Cardiovascular effects of an organophosphate toxin isolated from Ptychodiscus brevis - Mazumder_1997_Biomed.Environ.Sci_10_85
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Title : Central nicotinic receptor blockade inhibits emotionally conditioned pressor responses in rats - Kubo_1996_Experientia_52_348
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Title : [Effects of drugs on re-excitability of synapses of isolated frog ganglia] - Sandorne_1996_Acta.Pharm.Hung_66_259
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Title : Acute toxicity of several organophosphorous insecticides and protection by cholinergic antagonists and 2-PAM on Artemia salina larvae - Sanchez-Fortun_1996_Arch.Environ.Contam.Toxicol_31_391
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Title : Use of C1300 neuroblastoma cells to evaluate the protective value of hexamethonium, trimethaphan, hemicholinium, and triethylcholine against diisopropyl phosphorofluoridate toxicity - Hong_1995_J.Pharmaceutical.Scis_84_65
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Title : Differential effects of peripheral site ligands on Torpedo and chicken acetylcholinesterase - Eichler_1994_Mol.Pharmacol_45_335
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Title : Acetylcholinesterase peripheral anionic site degeneracy conferred by amino acid arrays sharing a common core - Barak_1994_J.Biol.Chem_269_6296
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Title : Histochemical and functional evidence for a cholinergic innervation of the equine ureter - Prieto_1994_J.Autonom.Nerv.Syst_47_159
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Title : Acetylcholinesterase as polyelectrolyte: interaction with multivalent cationic inhibitors - Tougu_1993_Biochim.Biophys.Acta_1157_199
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PubMedSearch : Tougu_1993_Biochim.Biophys.Acta_1157_199
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Title : Secretion of acetylcholinesterase and butyrylcholinesterase from the guinea-pig isolated ileum - Appleyard_1989_Br.J.Pharmacol_97_490
Author(s) : Appleyard ME , Smith AD
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PubMedSearch : Appleyard_1989_Br.J.Pharmacol_97_490
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Title : Inhibition of acetyl- and butyrylcholinesterase and amylase release from canine pancreas - Oguchi_1989_Pancreas_4_423
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Title : Effects of some mono- and bisquaternary ammonium compounds on the reactivatability of soman-inhibited human acetylcholinesterase in vitro - Hallek_1988_Biochem.Pharmacol_37_819
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Title : Structure-activity relationship of reversible cholinesterase inhibitors including paraquat - Seto_1988_Arch.Toxicol_62_37
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Title : Effects of cholinergic drugs on muscle contraction in Moniliformis moniliformis (Acanthocephala) - Sangster_1987_J.Parasitol_73_998
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Title : Selective facilitatory effect of vasoactive intestinal polypeptide (VIP) on muscarinic firing in vesical ganglia of the cat - Kawatani_1985_Brain.Res_336_223
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Title : Efficacy and toxicity of drug combinations in treatment of physostigmine toxicosis - Klemm_1983_Toxicology_27_41
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Title : The ganglionic blocking properties of the cholinesterase reactivator, HS-6 - Lundy_1978_Can.J.Physiol.Pharmacol_56_857
Author(s) : Lundy PM
Ref : Canadian Journal of Physiology & Pharmacology , 56 :857 , 1978
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Title : Effects of organophosphate insecticides on the cholinergic receptors of frog skeletal muscle - Dekin_1978_J.Pharmacol.Exp.Ther_205_319
Author(s) : Dekin MS , Guy HR , Edwards C
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Title : Differences in subunit activities in acetylcholinesterase as possible cause for apparent deviation from normal Michaelis-Menten kinetics - Gentinetta_1976_Biochim.Biophys.Acta_438_437
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Ref : Biochimica & Biophysica Acta , 438 :437 , 1976
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