Amylocaine hydrochlorideProduct ingredient for Amylocaine
- Name
- Amylocaine hydrochloride
- Drug Entry
- Amylocaine
Despite the introduction of using cocaine injections for regional anesthesia in 1884, non-addictive substitutes were sought after immediately 4. Finally, in 1903 the world's first synthetic and non-addictive local anesthetic, amylocaine, was synthesized and patented under the name Forneaucaine by Ernest Fourneau at the Pasteur Institute 4. Elsewhere in English speaking countries it was referred to as Stovaine, given the meaning of the French word 'fourneau' as 'stove' in English 4.
Although amylocaine could be administered topically or injected, it was most widely used for spinal anesthesia 4. Even though it certainly possessed less severe side effects than cocaine 4, the eventual development and clinical use of newer, more effective, and even safer local anesthetics like lidocaine, bupivicaine, and prilocaine in the 1940s and 1950s superseded and made the use of amylocaine obsolete.
- Accession Number
- DBSALT001127
- Structure
- Synonyms
- Amylocaine HCl
- UNII
- 224EF0K14Q
- CAS Number
- 532-59-2
- Weight
- Average: 271.79
Monoisotopic: 271.1339067 - Chemical Formula
- C14H22ClNO2
- InChI Key
- YCAXNWFCHTZUMD-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H21NO2.ClH/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12;/h6-10H,5,11H2,1-4H3;1H
- IUPAC Name
- 1-(dimethylamino)-2-methylbutan-2-yl benzoate hydrochloride
- SMILES
- Cl.CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1
- External Links
- ChemSpider
- 10311
- ChEMBL
- CHEMBL1718204
- Predicted Properties
Property Value Source Water Solubility 1.06 mg/mL ALOGPS logP 2.73 ALOGPS logP 3.22 Chemaxon logS -2.3 ALOGPS pKa (Strongest Basic) 8.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 29.54 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 69.68 m3·mol-1 Chemaxon Polarizability 26.84 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon