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more effective, and even safer local anesthetics like lidocaine, bupivicaine, and prilocaine in the 1940s and 1950s superseded and made the use of amylocaine obsolete.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
ChemSpider
10311
ChEMBL
CHEMBL1718204
Predicted Properties
PropertyValueSource
Water Solubility1.06 mg/mLALOGPS
logP2.73ALOGPS
logP3.22Chemaxon
logS-2.3ALOGPS
pKa (Strongest Basic)8.91Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area29.54 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity69.68 m3·mol-1Chemaxon
Polarizability26.84 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon