Structure via PubChem · Public domain (PubChem)
butacaine
Sign in to saveButacaine is a white crystalline ester used as a local anesthetic. It was first marketed in the 1920s.
Chemical data
- Formula
- C18H30N2O2
- Molecular weight
- 306.4 g/mol
- IUPAC name
- 3-(dibutylamino)propyl 4-aminobenzoate
- SMILES
- CCCCN(CCCC)CCCOC(=O)C1=CC=C(C=C1)N
- InChIKey
- HQFWVSGBVLEQGA-UHFFFAOYSA-N
- XLogP
- 4.5
- Polar surface area
- 55.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
55 papers- [Effect of procaine, nicotinoylprocaine and butacaine on mammalian cells in culture].Arzneimittel-Forschung · 1984
- Phospholipids as ionophores.The Journal of biological chemistry · 1976
- [Dimorphism of butacaine sulfate].Arzneimittel-Forschung · 1974
- Inhibition by local anaesthetics of adenine nucleotide translocation in rat liver mitochondria.The Biochemical journal · 1974
- The effect of butacaine on adenine nucleotide binding and translocation in rat liver mitochondria.The Biochemical journal · 1975
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 306.231
Show 5 more facts
- chemical formula
- C₁₈H₃₀N₂O₂
- canonical SMILES
- CCCCN(CCCC)CCCOC(=O)C1=CC=C(C=C1)N
- medical condition treated
- pain
- subject has role
- local anesthetic
- Commons category
- Butacaine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Butacaine is a white crystalline ester used as a local anesthetic. It was first marketed in the 1920s.
==Synthesis== The addition of metallic sodium to a mixture of allyl alcohol (1) and dibutylamine (2) gives the conjugate addition product 3-dibutylamino-1-propanol (3). Reaction of this intermediate with p-nitrobenzoyl chloride (4) gives the ester 5. A Béchamp reduction of the nitro group completes the synthesis of butacaine (6). thumb|500px|center|Synthesis of butacaine
Excerpted from Wikipedia’s “butacaine” article, available under the CC BY-SA 4.0 licence.