Butacaine
Chemical compound
From Wikipedia, the free encyclopedia
Butacaine is a white crystalline ester used as a local anesthetic.[1] It was first marketed in the 1920s.[1]
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| Names | |
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| Preferred IUPAC name
3-(Dibutylamino)propyl 4-aminobenzoate | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.005.214 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C18H30N2O2 | |
| Molar mass | 306.450 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The addition of metallic sodium to a mixture of allyl alcohol (1) and dibutylamine (2)[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).[3][4][5][6][7][8]
Synthesis of butacaine
