2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride, hydrate (1:1:1)
Basic information
- CAS
73360-54-0- Standard SMILES
CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C.Cl.O- InChIKey
HUCIWBPMHXGLFM-UHFFFAOYSA-N- Molecular formula
- C18H31ClN2O2
- Average molar mass
- 342.9 g/mol
- Monoisotopic mass
- 342.2074059
Overview
Bupivacaine hydrochloride hydrate is a racemate composed of equimolar amounts of dextrobupivacaine hydrochloride hydrate and levobupivacaine hydrochloride hydrate. A piperidinecarboxamide-based local anaesthetic, it has a slow onset and long duration of action. It has a role as a local anaesthetic, an EC 3.1.1.8 (cholinesterase) inhibitor, an adrenergic antagonist, an amphiphile and an EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor. It contains a bupivacaine hydrochloride (anhydrous), a levobupivacaine hydrochloride hydrate and a dextrobupivacaine hydrochloride hydrate.
Names & identifiers
- Preferred name
- 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride, hydrate (1:1:1)
- IUPAC
- 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrate;hydrochloride
- English name
- Bupivacaine Hydrochloride
- Molecular formula
- C18H31ClN2O2
- Molecular weight
- 342.91
Names & synonyms
DTXSID5013237792-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride, hydrate (1:1:1)RefChem:478278DTXCID80175318973360-54-0Bupivacaine hydrochloride hydrate(+/-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride, monohydrateBupivacaine (hydrochloride monohydrate)1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrate;hydrochlorideBupivacaine HCl H2-OUNII-7TQO7W3VT8Bupivacaine hydrochloride [EP]
Show more names
Bupivacaine HCl hydrateBupivacaine HCl H2O IP/USP/BP/EPBupivacaine Hydrochloride (300 mg)Bupivacaine Hydrochloride (500 mg)1-Butyl-N-(2,6-dimethylphenyl)piperidin-2-carboxamide HCl hydrate (1:1:1)1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride hydrateBupivacaine Hydrochloride Monohydrate 1.0 mg/ml in Methanol (as anhydrous free base)1-butyl-N-(2,6-dimethylphenyl)-2-Piperidinecarboxamide hydrochloride hydrate (1:1:1)
Properties
Computed structural properties
- Topological polar surface area
- 33.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 321
Physicochemical properties
- Melting point
- 255 · 255-259℃
- RTECS
- 6125000 · TK6125000
- storage temp.
- room temp
- solubility
- DMSO (Slightly), Methanol (Slightly), Water (Slightly)
- form
- solid
- Water Solubility
- 50 mM, · Soluble in water to 50 mM, in DMSO to 100 mM and in ethanol to 100 mM.
- Major Application
- forensics and toxicologypharmaceutical (small molecule)veterinary
- InChI
- InChI=1S/C18H28N2O.ClH.H2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H;1H2
- InChIKey
- HUCIWBPMHXGLFM-UHFFFAOYSA-N
- SMILES
- C(C1CCCCN1CCCC)(=O)NC1C(=CC=CC=1C)C.Cl.O
- FDA UNII
- 7 TQO7W3VT8 · 7TQO7W3VT8
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
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
H300+H310+H330 (95.1%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 1 (97.6%)
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGII
- risk_code
- 26/27/28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 22-36/37/39-45
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard statements
- H300+H310+H330
- Hazard Classifications
- Acute Tox. 1 InhalationAcute Tox. 2 DermalAcute Tox. 2 Oral
- Precautionary statements
Chemistry & industry
Applications
UsesIt is employed as Na+ channel blocker, local anesthetic and cAMP production inhibitor. It acts as a surfactant molecule possessing both hydrophilic and lipophilic properties, adrenergic antagonist, EC 3.1.1.8 (cholinesterase) inhibitor and EC 3.6.3.8 (Ca(2+)-transporting ATPase) inhibitor.
Additional notes
DefinitionChEBI: A racemate composed of equimolar amounts of dextrobupivacaine hydrochloride hydrate and levobupivacaine hydrochloride hydrate. A piperidinecarboxamide-based local anaesthetic, it has a slow onset and long duration of action.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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