Amylocaine
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Amylocaine
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CAS No:
644-26-8
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Formula:
C14H21NO2
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Chemical Name:
Amylocaine
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Synonyms:
2-Butanol,1-(dimethylamino)-2-methyl-,2-benzoate;2-Butanol,1-(dimethylamino)-2-methyl-,benzoate (ester);Amyleine;Amylocaine;Stovaine;Stovain;1-[(Dimethylamino)methyl]-1-methylpropyl benzoate
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CAS No:
Description
Stovaine is a benzoate ester.|Despite the introduction of using cocaine injections for regional anesthesia in 1884, non-addictive substitutes were sought after immediately. 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. Elsewhere in English speaking countries it was referred to as Stovaine, given the meaning of the French word 'fourneau' as 'stove' in English. Although amylocaine could be administered topically or injected, it was most widely used for spinal anesthesia. Even though it certainly possessed less severe side effects than cocaine, 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more effective, and even safer local anesthetics like lidocaine, bupivicaine, and prilocaine in the 1940s and 1950s superseded and made the use of amylocaine obsolete.
Characteristics
29.54000
2.57370
1.007g/cm3
183 °C
310.7ºC at 760 mmHg
103.5ºC
1.506
LDLo ivn-rat: 25 mg/kg PHREA7 12,262,32
Toxicity
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s.
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s.
Drug Information
The most common indication for the usage of amylocaine was spinal anesthesia.
Like all other local anesthetics, amylocaine acts as a membrane stabilizing drug that reversibly decreases the rate of depolarization and depolarization of excitable membranes. In this way, the conduction of neuronal signals for certain bodily movements can be blocked. In particular, when administered for spinal anesthesia, the resultant anesthesia can typically extend from the chest to the legs.
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s.
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s.
A lack of detailed information regarding the specificities of amylocaine relate to a lack of information on its pharmacokinetics at the time of its primary use in the early 1900s.
In particular, amylocaine, much like other local anesthetics, bind and blockade voltage gated sodium channels located in the excitable membranes of various sensory receptors. Once blocked, the influx of sodium across the channels and membrane is inhibited. Because the influx of sodium is necessary to facilitate neuronal action potentials and signal conduction across sensory receptor membranes, the influx inhibition subsequently prevents the body reactions that would normally result from the neuronal signals.
Amyleine
Computed Properties
Molecular Weight:235.32
XLogP3:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:235.157228913
Monoisotopic Mass:235.157228913
Topological Polar Surface Area:29.5
Heavy Atom Count:17
Complexity:247
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes