benzoquinonium profile

Benzoquinonium is a synthetic quaternary ammonium compound that acts as a potent neuromuscular blocking agent. Its synthesis typically involves the reaction of a suitable quinoline derivative with a dihaloalkane. Benzoquinonium exhibits a fast onset and short duration of action, leading to paralysis of skeletal muscles. It was initially studied for its potential use as a muscle relaxant in surgical procedures. However, due to its rapid action and short duration, it has not found widespread clinical application. Research on benzoquinonium has focused on understanding its mechanism of action and exploring its potential for specific medical applications, such as in the treatment of muscle spasms or for diagnostic purposes.'

benzoquinonium: RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	9394
CHEMBL ID	1358790
CHEBI ID	173301
SCHEMBL ID	12648552
MeSH ID	M0046247

Synonym
7554-16-7
CHEBI:173301
benzyl-[3-[[4-[3-[benzyl(diethyl)azaniumyl]propylamino]-3,6-dioxocyclohexa-1,4-dien-1-yl]amino]propyl]-diethylazanium
tocris-0424
NCGC00024582-01
NCGC00163229-01
benzoquinonium
t91wj82joz ,
unii-t91wj82joz
benzenemethanaminium, n,n'-((3,6-dioxo-1,4-cyclohexadiene-1,4-diyl)bis(imino-3,1-propanediyl))bis(n,n-diethyl-
CHEMBL1358790
9025-57-4
benzoquinonium cation
n,n'-((3,6-dioxo-1,4-cyclohexadiene-1,4-diyl)bis(imino-3,1-propanediyl))bis(n,n-diethylbenzenemethanaminium
benzoquinonium ion
SCHEMBL12648552
benzyl({3-[(4-{[3-(benzyldiethylazaniumyl)propyl]amino}-3,6-dioxocyclohexa-1,4-dien-1-yl)amino]propyl})diethylazanium
311-09-1 (di-chloride)
1,4-b-d-xylan xylanohydrolase
pentosanase
e.c. 3.2.1.8
DTXSID60997003
n~1~,n~4~-bis{3-[benzyl(diethyl)azaniumyl]propyl}-3,6-bis(oxidaniumylidene)cyclohexa-1,4-diene-1,4-bis(aminide)
benzoquinonium-dibromide
Q27289827

Excerpt	Reference	Relevance
"Benzoquinonium (Mytolon) has been shown to produce a curare-like rather than a decamethonium-like paralysis of neuromuscular transmission in the tibialis anterior and soleus muscle of cats and the gastrocnemius muscle of hens. "	( The neuromuscular blocking action of benzoquinonium chloride in the cat and in the hen. BOWMAN, WC, 1958)	1.95

Class	Description
aromatic amine	An amino compound in which the amino group is linked directly to an aromatic system.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASE	Homo sapiens (human)	Potency	1.4125	0.0032	45.4673	12,589.2998	AID2517
USP1 protein, partial	Homo sapiens (human)	Potency	63.0957	0.0316	37.5844	354.8130	AID504865
lethal factor (plasmid)	Bacillus anthracis str. A2012	Potency	1.2589	0.0200	10.7869	31.6228	AID912
Inositol monophosphatase 1	Rattus norvegicus (Norway rat)	Potency	11.2202	1.0000	10.4756	28.1838	AID1457
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Assay ID	Title	Year	Journal	Article
AID1508630	Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay	2021	Cell reports, 04-27, Volume: 35, Issue:4	A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347154	Primary screen GU AMC qHTS for Zika virus inhibitors	2020	Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49	Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	14 (50.00)	18.7374
1990's	8 (28.57)	18.2507
2000's	3 (10.71)	29.6817
2010's	1 (3.57)	24.3611
2020's	2 (7.14)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	32 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
carbamates [no description available]	1.97	1	amino-acid anion
choline [no description available]	1.93	1	cholines	allergen; Daphnia magna metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; neurotransmitter; nutrient; plant metabolite; Saccharomyces cerevisiae metabolite
phenol [no description available]	2.05	1	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
decamethonium decamethonium: RN given refers to parent cpd. decamethonium : A quaternary ammonium ion that is a depolarising muscle relaxant whose structure comprises a decane-1,10-diamine core in which each amino group carries three methyl substituents.	1.93	1	quaternary ammonium ion	muscle relaxant; nicotinic acetylcholine receptor agonist
edrophonium Edrophonium: A rapid-onset, short-acting cholinesterase inhibitor used in cardiac arrhythmias and in the diagnosis of myasthenia gravis. It has also been used as an antidote to curare principles.. edrophonium : A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.	2.34	2	phenols; quaternary ammonium ion	antidote; diagnostic agent; EC 3.1.1.8 (cholinesterase) inhibitor
hexamethonium 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.	1.98	1	quaternary ammonium salt
mecamylamine Mecamylamine: A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.	1.97	1	primary aliphatic amine
neostigmine Neostigmine: A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.. neostigmine : A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.	2.34	2	quaternary ammonium ion	antidote to curare poisoning; EC 3.1.1.7 (acetylcholinesterase) inhibitor
quinone benzoquinone : The simplest members of the class of benzoquinones, consisting of cyclohexadiene which is substituted by two oxo groups.. 1,4-benzoquinone : The simplest member of the class of 1,4-benzoquinones, obtained by the formal oxidation of hydroquinone to the corresponding diketone. It is a metabolite of benzene.. quinone : Compounds having a fully conjugated cyclic dione structure, such as that of benzoquinones, derived from aromatic compounds by conversion of an even number of -CH= groups into -C(=O)- groups with any necessary rearrangement of double bonds (polycyclic and heterocyclic analogues are included).	1.92	1	1,4-benzoquinones	cofactor; human xenobiotic metabolite; mouse metabolite
succinylcholine Succinylcholine: A quaternary skeletal muscle relaxant usually used in the form of its bromide, chloride, or iodide. It is a depolarizing relaxant, acting in about 30 seconds and with a duration of effect averaging three to five minutes. Succinylcholine is used in surgical, anesthetic, and other procedures in which a brief period of muscle relaxation is called for.. succinylcholine : A quaternary ammonium ion that is the bis-choline ester of succinic acid.	1.93	1	quaternary ammonium ion; succinate ester	drug allergen; muscle relaxant; neuromuscular agent
sulfasalazine Sulfasalazine: A drug that is used in the management of inflammatory bowel diseases. Its activity is generally considered to lie in its metabolic breakdown product, 5-aminosalicylic acid (see MESALAMINE) released in the colon. (From Martindale, The Extra Pharmacopoeia, 30th ed, p907). sulfasalazine : An azobenzene consisting of diphenyldiazene having a carboxy substituent at the 4-position, a hydroxy substituent at the 3-position and a 2-pyridylaminosulphonyl substituent at the 4'-position.	2.21	1
carbachol Carbachol: A slowly hydrolyzed CHOLINERGIC AGONIST that acts at both MUSCARINIC RECEPTORS and NICOTINIC RECEPTORS.	1.96	1	ammonium salt; carbamate ester	cardiotonic drug; miotic; muscarinic agonist; nicotinic acetylcholine receptor agonist; non-narcotic analgesic
dimethylphenylpiperazinium iodide Dimethylphenylpiperazinium Iodide: A selective nicotinic cholinergic agonist used as a research tool. DMPP activates nicotinic receptors in autonomic ganglia but has little effect at the neuromuscular junction.	1.97	1	N-arylpiperazine; organic iodide salt; piperazinium salt; quaternary ammonium salt	nicotinic acetylcholine receptor agonist
physostigmine Physostigmine: A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity.	3.06	5	carbamate ester; indole alkaloid	antidote to curare poisoning; EC 3.1.1.8 (cholinesterase) inhibitor; miotic
tubocurarine Tubocurarine: A neuromuscular blocker and active ingredient in CURARE; plant based alkaloid of Menispermaceae.. tubocurarine : A benzylisoquinoline alkaloid muscle relaxant which constitutes the active component of curare.. isoquinoline alkaloid : Any alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.	2.87	4	bisbenzylisoquinoline alkaloid	drug allergen; muscle relaxant; nicotinic antagonist
benzyl chloride benzyl chloride: RN given refers to unlabeled cpd. chlorophenylmethane : A chlorohydrocarbon that is phenylmethane substituted by a chloro group at unspecified position.. benzyl chloride : A member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.	1.92	1	benzyl chlorides
galantamine Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.	1.98	1	benzazepine alkaloid fundamental parent; benzazepine alkaloid; organic heterotetracyclic compound; tertiary amino compound	antidote to curare poisoning; cholinergic drug; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; plant metabolite
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.	2.03	1	ergoline alkaloid
myomodulin myomodulin: found in motor neuron B16 of Aplysia; amino acid sequence given in first source	1.98	1
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.03	1
genistein [no description available]	2.04	1	7-hydroxyisoflavones	antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; geroprotector; human urinary metabolite; phytoestrogen; plant metabolite; tyrosine kinase inhibitor
cesium Cesium: A member of the alkali metals. It has an atomic symbol Cs, atomic number 50, and atomic weight 132.91. Cesium has many industrial applications, including the construction of atomic clocks based on its atomic vibrational frequency.	1.97	1	alkali metal atom
tetrodotoxin Tetrodotoxin: An aminoperhydroquinazoline poison found mainly in the liver and ovaries of fishes in the order TETRAODONTIFORMES, which are eaten. The toxin causes paresthesia and paralysis through interference with neuromuscular conduction.. tetrodotoxin : A quinazoline alkaloid that is a marine toxin isolated from fish such as puffer fish. It has been shown to exhibit potential neutotoxicity due to its ability to block voltage-gated sodium channels.	2.39	2	azatetracycloalkane; oxatetracycloalkane; quinazoline alkaloid	animal metabolite; bacterial metabolite; marine metabolite; neurotoxin; voltage-gated sodium channel blocker
fmrfamide FMRFamide: A molluscan neuroactive peptide which induces a fast excitatory depolarizing response due to direct activation of amiloride-sensitive SODIUM CHANNELS. (From Nature 1995; 378(6558): 730-3)	2.39	2
cardiovascular agents Cardiovascular Agents: Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume.	3.31	7
pyrethrins [no description available]	1.96	1

Condition	Relationship Strength	Studies
Congenital Zika Syndrome [description not available]	2.25	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.5	2
Zika Virus Infection A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.	2.25	1
Innate Inflammatory Response [description not available]	2.21	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	2.21	1
Electrolytes Substances that dissociate into two or more ions, to some extent, in water. Solutions of electrolytes thus conduct an electric current and can be decomposed by it (ELECTROLYSIS). (Grant & Hackh's Chemical Dictionary, 5th ed)	2.05	1
Amyotonia Congenita [description not available]	1.93	1
Palsy [description not available]	1.93	1
Neuromuscular Diseases A general term encompassing lower MOTOR NEURON DISEASE; PERIPHERAL NERVOUS SYSTEM DISEASES; and certain MUSCULAR DISEASES. Manifestations include MUSCLE WEAKNESS; FASCICULATION; muscle ATROPHY; SPASM; MYOKYMIA; MUSCLE HYPERTONIA, myalgias, and MUSCLE HYPOTONIA.	1.93	1
Paralysis A general term most often used to describe severe or complete loss of muscle strength due to motor system disease from the level of the cerebral cortex to the muscle fiber. This term may also occasionally refer to a loss of sensory function. (From Adams et al., Principles of Neurology, 6th ed, p45)	1.93	1
Neuromuscular Blockade The intentional interruption of transmission at the NEUROMUSCULAR JUNCTION by external agents, usually neuromuscular blocking agents. It is distinguished from NERVE BLOCK in which nerve conduction (NEURAL CONDUCTION) is interrupted rather than neuromuscular transmission. Neuromuscular blockade is commonly used to produce MUSCLE RELAXATION as an adjunct to anesthesia during surgery and other medical procedures. It is also often used as an experimental manipulation in basic research. It is not strictly speaking anesthesia but is grouped here with anesthetic techniques. The failure of neuromuscular transmission as a result of pathological processes is not included here.	1.93	1
Muscle Relaxation That phase of a muscle twitch during which a muscle returns to a resting position.	1.92	1
Cystic Fibrosis of Pancreas [description not available]	2.04	1
Cystic Fibrosis An autosomal recessive genetic disease of the EXOCRINE GLANDS. It is caused by mutations in the gene encoding the CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR expressed in several organs including the LUNG, the PANCREAS, the BILIARY SYSTEM, and the SWEAT GLANDS. Cystic fibrosis is characterized by epithelial secretory dysfunction associated with ductal obstruction resulting in AIRWAY OBSTRUCTION; chronic RESPIRATORY INFECTIONS; PANCREATIC INSUFFICIENCY; maldigestion; salt depletion; and HEAT PROSTRATION.	2.04	1
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.98	1

benzoquinonium

Description

Cross-References

Synonyms (25)

Research Excerpts

Effects

Drug Classes (1)

Protein Targets (4)

Potency Measurements

Bioassays (2)

Research

Studies (28)

Market Indicators

Research Demand Index: 64.50

Study Types