Structure via PubChem · Public domain (PubChem)
etidocaine
Sign in to saveAlso known as (+-)-N-(2,6-dimethylphenyl)-2-(ethylpropylamino)butanamide, (+-)-2-(ethylpropylamino)-2',6'-butyroxylidide
Etidocaine, marketed under the trade name Duranest, is an amide-type local anesthetic given by injection during surgical procedures and labor and delivery. Etidocaine has a long duration of activity, and the main disadvantage of use during dentistry is increased bleeding during surgery. ==Synthesis== thumb|center|500px|Patent: 2-bromobutyryl chloride synthesis: The amide reaction between 2,6-xylidine (1) and 2-bromobutyryl chloride [22118-12-3] (2) gives 2-Bromo-N-(2,6-Dimethylphenyl)Butanamide [53984-81-9] (3). Alkylation with N-Ethylpropylamine [20193-20-8] (4) gives Etidocaine (5).
Chemical data
- Formula
- C17H28N2O
- Molecular weight
- 276.4 g/mol
- IUPAC name
- N-(2,6-dimethylphenyl)-2-[ethyl(propyl)amino]butanamide
- SMILES
- CCCN(CC)C(CC)C(=O)NC1=C(C=CC=C1C)C
- InChIKey
- VTUSIVBDOCDNHS-UHFFFAOYSA-N
- XLogP
- 3.7
- Polar surface area
- 32.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1976
- Admin. routes
- parenteral
via ChEMBL · EBI
Research
394 papers- Toxic systemic reactions of bupivacaine and etidocaine.Oral surgery, oral medicine, oral pathology, oral radiology, and endodontics · 1995
- From cocaine to ropivacaine: the history of local anesthetic drugs.Current topics in medicinal chemistry · 2001
- Etidocaine in dentistry.Anesthesia progress · 1989
- Cardiac arrest following regional anesthesia with etidocaine or bupivacaine.Anesthesiology · 1979
- Etidocaine, bupivacaine, and lidocaine seizure thresholds in monkeys.Anesthesiology · 1975
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 276.220164
- Has use
- medication
Show 6 more facts
- Commons category
- Etidocaine
- chemical formula
- C₁₇H₂₈N₂O
- medical condition treated
- pain
- World Health Organisation international non-proprietary name
- etidocaine
- canonical SMILES
- CCCN(CC)C(CC)C(=O)NC1=C(C=CC=C1C)C
- subject has role
- local anesthetic
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- References
- External links
Etidocaine, marketed under the trade name Duranest, is an amide-type local anesthetic given by injection during surgical procedures and labor and delivery. Etidocaine has a long duration of activity, and the main disadvantage of use during dentistry is increased bleeding during surgery. ==Synthesis== thumb|center|500px|Patent: 2-bromobutyryl chloride synthesis: The amide reaction between 2,6-xylidine (1) and 2-bromobutyryl chloride [22118-12-3] (2) gives 2-Bromo-N-(2,6-Dimethylphenyl)Butanamide [53984-81-9] (3). Alkylation with N-Ethylpropylamine [20193-20-8] (4) gives Etidocaine (5).
== References ==
Excerpted from Wikipedia’s “etidocaine” article, available under the CC BY-SA 4.0 licence.