Butacaine

Butacaine is a white crystalline ester used as a local anesthetic.^[1] It was first marketed in the 1920s.^[1]

Butacaine

Names
Preferred IUPAC name 3-(Dibutylamino)propyl 4-aminobenzoate
Identifiers
CAS Number	149-16-6
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL129529
ChemSpider	2386
ECHA InfoCard	100.005.214
PubChem CID	2480
UNII	Z84S23CGJJ Y
CompTox Dashboard (EPA)	DTXSID3045300
InChI InChI=1/C18H30N2O2/c1-3-5-12-20(13-6-4-2)14-7-15-22-18(21)16-8-10-17(19)11-9-16/h8-11H,3-7,12-15,19H2,1-2H3 Key: HQFWVSGBVLEQGA-UHFFFAOYAZ
SMILES O=C(OCCCN(CCCC)CCCC)c1ccc(N)cc1
Properties
Chemical formula	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). Infobox references

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

See also

• Isobucaine