Succinylcholine Chloride
Basic information
- CAS
71-27-2- Standard SMILES
C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C.[Cl-].[Cl-]- InChIKey
YOEWQQVKRJEPAE-UHFFFAOYSA-L- Molecular formula
- C14H30N2O4.2Cl
- Average molar mass
- 361.3 g/mol
- Monoisotopic mass
- 360.1582628
Overview
Suxamethonium dichloride is a fine white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- Succinylcholine Chloride
- IUPAC
- trimethyl-[2-[4-oxo-4-[2-(trimethylazaniumyl)ethoxy]butanoyl]oxyethyl]azanium dichloride
- English name
- Succinylcholine Chloride
- Molecular formula
- C14H30Cl2N2O4
- Molecular weight
- 361.3
Names & synonyms
Succinylcholine chloride71-27-2Succinyldicholine chlorideAnectineMidarineScolineAnectine chlorideSuxamethonii chloridumLysthenoneMyopleginePantolaxSucostrin
Show more names
SUXAMETHONIUM CHLORIDEDITILINskolinLYSTHENONSUCCICURAN
SukolinSuxinylSuccinyl-astaScoline chlorideCloruro de suxametonioQuelicin chlorideSucostrin chlorideChlorsuccinylcholin
Database identifiers
- CAS
71-27-2- PubChem CID
- 22475
- DTXSID
DTXSID1023603- ChEMBL
CHEMBL983- ChEBI
CHEBI:61219- UNII
- I9L0DDD30I
- EC Number
- 200-747-4
Properties
Computed structural properties
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 11
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 284
Experimental & physicochemical properties
Solubilitygreater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point313 to 325 °F (NTP, 1992)
Physical DescriptionSuxamethonium dichloride is a fine white powder. (NTP, 1992)
Physicochemical properties
- Melting point
- 164 °C · 164 °C
- storage temp.
- Refrigerator
- solubility
- Methanol (Slightly), Water (Slightly)
- form
- Solid
- color
- White to Off-White
- Merck
- 8875 · 8875
- Stability
- Stable. Combustible. Incompatible with strong oxidizing agents.
- CAS DataBase Reference
- 71 · 71-27-2(CAS DataBase Reference)
- FDA UNII
- 9 L0DDD30I · I9L0DDD30I
- NCI Drug Dictionary
- Anectine
- EPA Substance Registry System
- Succinylcholine chloride (71-27-2)
- Protein binding
- 70 % · 70%
- Excreted unchanged in urine
- 10 % · <10%
- Biological half-life
- 2 · 2-3 minutes / -
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 315 · H315-H332-H301-H335-H319-H311
- Precautionary statements
- 264 · P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P312-P264-P280-P305+P351+P338-P337+P313P-P280-P302+P352-P312-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
- Safety Statements
- 7 · 7/8
- RIDADR
- 3249 · 3249
- RTECS
- 2360000 · GA2360000
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Toxicity
- 50 i.v · LD50 i.v. in mice: 0.45 mg/kg (Anttila, Ertama)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (93.1%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 29 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - Ethanaminium, 2,2'-[(1,4-dioxo-1,4-butanediyl)bis(oxy)]bis[N,N,N-trimethyl-, dichloride: Environment tier I assessment
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include relaxation of skeletal muscles, particularly those of the abdominal wall.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 3 (93.1%)
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)
Toxicology
Adverse Effects
Hyperkalemia is the most common adverse effect of succinylcholine administration, attributed to the drug's stimulatory effect on skeletal muscles. Serum potassium levels may increase as much as 0.5 mEq/L, which is clinically insignificant unless a predisposition to hyperkalemia exists as a result of disease pathophysiology that induces upregulation of postjunctional acetylcholine receptors. Succinylcholine is contraindicated for patients with these conditions. If hyperkalemia is sufficient to create electrocardiography changes, clinicians should avoid using succinylcholine in such circumstances. Special consideration is also necessary for those with chronically elevated potassium levels, such as renal failure patients, to not induce acute on chronic hyperkalemia. Succinylcholine should be avoided in patients with significant burns or traumatic injuries that are 24 to 72 hours post-injury due to the high probability of acute hyperkalemia that may become exacerbated as a result. Marked or untreated hyperkalemia may result in dysrhythmias or even death.
Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Succinylcholine chloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- rtecs
- GA2360000
- ridadr
- 3249
- Toxicity
- LD50 i.v. in mice: 0.45 mg/kg (Anttila, Ertama)
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- safety_code
- 7/8
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H315-H332-H301-H335-H319-H311
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P261-P271-P304+P340-P312-P264-P280-P305+P351+P338-P337+P313P-P280-P302+P352-P312-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
SUCCINYLCHOLINE CHLORIDE
Depolarizing Neuromuscular Blocker [EPC]; Neuromuscular Depolarizing Blockade [PE]
MeSH Pharmacological ClassificationDrugs that interrupt transmission at the skeletal neuromuscular junction by causing sustained depolarization of the motor end plate. These agents are primarily used as adjuvants in surgical anesthesia to cause skeletal muscle relaxation.
Applications
DescriptionSuccinylcholine chloride is a potent relaxant of voluntary striated muscle but has little direct effect on smooth muscle. It has no anesthetic or pain-obliterating properties; therefore, immobilized animals remain completely conscious although unable to move. The duration of effect is quite brief because succinylcholine is rapidly destroyed by non-specific cholinesterases in the blood plasma and liver. Immobilization lasts five to 12 minutes in man and horses and somewhat longer in other species,with ruminants generally requiring longest recovery periods (Stowe et al. 1958).Since the discovery of its curariform properties in 1949, succinylcholine has been widely used for immobilization of animals and in human surgical procedures. Several workers have used succinylcholine on bears (Black 1958, Knudsen 1959, Craighead et al. 1960, Troyer et al. 1961,Hornocker 1962, Mundy 1963,Pearson et al. 1968, Jonkel and Cowan 1971 and Mundy and Flook 1973).Succinylcholine chloride is indicated as an adjunct to general anesthesia, to facilitate tracheal intubation, and to provide skeletal muscle relaxation during surgery or mechanical ventilation.
UsesA neuromuscular blocking agent. Muscle relaxant (skeletal).
General DescriptionSuccinylcholine chloride,choline chloride succinate (2:1) (Anectine, Sucostrin),is a white, odorless, crystalline substance that is freely solublein water to give solutions with a pH of about 4. It isstable in acidic solutions but unstable in alkali. Aqueous solutionsshould be refrigerated to ensure stability.Succinylcholine chloride is characterized by a very shortduration of action and a quick recovery because of its rapidhydrolysis after injection. It brings about the typical muscularparalysis caused by blocking nervous transmission at themyoneural junction. Large doses may cause temporary respiratorydepression, as with similar agents. Its action, in contrastwith that of (1)-tubocurarine, is not antagonized byneostigmine, physostigmine, or edrophonium chloride.These anticholinesterase drugs actually prolong the action ofsuccinylcholine chloride, which suggests that the drug isprobably hydrolyzed by cholinesterases. The brief durationof action of this curare-like agent is said to render an antidoteunnecessary if the proper supportive measures are available.Succinylcholine chloride has a disadvantage, however, inthat the usual antidotes cannot terminate its action promptly.
General DescriptionFine white powder.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A chloride salt in which the negative charge of the chloride ions is balanced by succinylcholine dications.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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