Succinylcholine (CED0003400)

Record Information
Version1.0
Creation Date2016-05-25 18:18:58 UTC
Update Date2026-08-19 08:03:00 UTC
Accession NumberCHEM022065
Identification
Common NameSuccinylcholine
ClassSmall Molecule
Description
Succinylcholine is an organic compound with the formula C14H30N2O4 and an average molecular weight of 290.40 g/mol. Succinylcholine belongs to the quaternary ammonium salts, a subclass of organonitrogen compounds within the organic compounds. This compound is recorded as being found in or released from 20 sources. Within the healthcare, pharmaceuticals, and veterinary products category, it is used as a muscle relaxant. Other recorded sources include food preservation and the preparation of wine or sparkling wine. Additionally, it is associated with household cleaning and consumer products, such as tobacco smoke filters, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is also found in electrical and electronic equipment, including antennas, conductors or conductive bodies characterised by the conductive materials, cores yokes or armatures, electric switches, and electrically stimulated smoking devices, among eight other sources. Recorded routes of exposure for the compound include intravenous, intramuscular, and parenteral administration. Succinylcholine interacts with 13 recorded protein targets. It acts as an agonist of the muscarinic acetylcholine receptor M2 (CHRM2), the muscarinic acetylcholine receptor M3 (CHRM3), the neuronal acetylcholine receptor subunit beta-2 (CHRNB2), and the neuronal acetylcholine receptor subunit alpha-5 (CHRNA5), as well as nine other proteins.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
2,2'-[(1,4-DIOXOBUTANE-1,4-diyl)bis(oxy)]bis(N,N,N-trimethylethanaminium)ChEBI
Dicholine succinateChEBI
Succinic acid, diester with cholineChEBI
SuccinocholineChEBI
SuccinoylcholineChEBI
SuccinylbischolineChEBI
SuccinyldicholineChEBI
SuxamethoniumChEBI
Dicholine succinic acidGenerator
Succinate, diester with cholineGenerator
ScolineHMDB
Succinylcholine chlorideHMDB
Suxamethonium chlorideHMDB
Bromide, suxamethoniumHMDB
Succinylcholine dichlorideHMDB
Succinylcholine dichloride, di H2OHMDB
Suxamethonium bromideHMDB
AnectineHMDB
Dibromide, succinylcholineHMDB
Diiodide, succinylcholineHMDB
Diperchlorate, succinylcholineHMDB
ListenonHMDB
SuccicuranHMDB
Succinylcholine dibromideHMDB
Succinylcholine iodideHMDB
Dichloride, succinylcholineHMDB
DitilinHMDB
CelocurineHMDB
LysthenonHMDB
MyorelaxinHMDB
QuelicinHMDB
Succinylcholine dichloride, di-H2OHMDB
Succinylcholine diiodideHMDB
Succinylcholine diperchlorateHMDB
Succinate, dicholineHMDB
Chemical FormulaC14H30N2O4
Average Molecular Mass290.399 g/mol
Monoisotopic Mass290.221 g/mol
CAS Registry Number306-40-1
IUPAC Nametrimethyl[2-({4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl}oxy)ethyl]azanium
Traditional Namesuccinylcholine
SMILESC[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C
InChI IdentifierInChI=1S/C14H30N2O4/c1-15(2,3)9-11-19-13(17)7-8-14(18)20-12-10-16(4,5)6/h7-12H2,1-6H3/q+2
InChI KeyAXOIZCJOOAYSMI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentAcyl cholines
Alternative Parents
Substituents
  • Acyl choline
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Amine
  • Organooxygen compound
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00076 g/LALOGPS
logP-2.5ALOGPS
logP-8.4ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity100.94 m³·mol⁻¹ChemAxon
Polarizability33.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
888.0Log mg/kg[500:1600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
365Muscle relaxantsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)9.57545
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)5.83869
Muscarinic acetylcholine receptor M5 structureClick to view 3D structureMuscarinic acetylcholine receptor M5P08912HumansPredicted (SEA)4.82665
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)12.0666
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)19.3845
Click to view 3D structureShort transient receptor potential channel 4Q9QUQ5Mus musculusPredicted (SEA)13.4679
Click to view 3D structureMuscarinic acetylcholine receptor M1P08482Rattus norvegicusPredicted (SEA)75.5137
Click to view 3D structureMuscarinic acetylcholine receptor M2P10980Rattus norvegicusPredicted (SEA)51.614
Click to view 3D structureMuscarinic acetylcholine receptor M3P08483Rattus norvegicusPredicted (SEA)38.1461
Click to view 3D structureMuscarinic acetylcholine receptor M4P08485Rattus norvegicusPredicted (SEA)24.7561
Click to view 3D structureMitochondrial carnitine/acylcarnitine carrier proteinO43772HumansPredicted (SEA)4.98235
Click to view 3D structureAcetylcholinesteraseP21836Mus musculusPredicted (SEA)177.963
Click to view 3D structureMuscarinic acetylcholine receptor M3Q8VH26Cavia porcellusPredicted (SEA)83.2208
Neuronal acetylcholine receptor subunit alpha-7 structureClick to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P36544HumansPredicted (SEA)494.576
High affinity choline transporter 1 structureClick to view 3D structureHigh affinity choline transporter 1Q9GZV3HumansPredicted (SEA)429.728
Click to view 3D structureAcetylcholine receptor subunit deltaP02718Torpedo californicaPredicted (SEA)0.467095
Autotaxin structureClick to view 3D structureAutotaxinQ13822HumansPredicted (SEA)178.82
Click to view 3D structureLysophosphatidic acid receptor 3Q9UBY5HumansPredicted (SEA)116.93
Lysophosphatidic acid receptor 1 structureClick to view 3D structureLysophosphatidic acid receptor 1Q92633HumansPredicted (SEA)178.742
Lysophosphatidic acid receptor 2 structureClick to view 3D structureLysophosphatidic acid receptor 2Q9HBW0HumansPredicted (SEA)90.7722
Click to view 3D structureCytochrome P450 2C23P24470Rattus norvegicusPredicted (SEA)11.5217
Click to view 3D structureGalanin receptor type 3O60755HumansPredicted (SEA)156.555
Click to view 3D structureMuscarinic acetylcholine receptor M1P12657Mus musculusPredicted (SEA)3.19182
Click to view 3D structureAcetylcholine-binding proteinP58154Lymnaea stagnalisPredicted (SEA)278.233
Click to view 3D structureNeuronal acetylcholine receptor subunit alpha-7Q05941Rattus norvegicusPredicted (SEA)621.704
Concentrations
Not Available
External Links
DrugBank IDDB00202
HMDB IDHMDB0014347
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSCK
Wikipedia LinkSuxamethonium chloride
Chemspider ID5123
ChEBI ID45652
PubChem Compound ID5314
Kegg Compound IDC07546
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jonsson M, Dabrowski M, Gurley DA, Larsson O, Johnson EC, Fredholm BB, Eriksson LI: Activation and inhibition of human muscular and neuronal nicotinic acetylcholine receptors by succinylcholine. Anesthesiology. 2006 Apr;104(4):724-33.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11123992
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=13063382
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17667569
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23223104
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23838346
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24018151
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=29368335
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=4032432
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6196640
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=7526642
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9435889