Identification

Name
Amylocaine
Accession Number
DB09088
Type
Small Molecule
Groups
Approved, Withdrawn
Description

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more effective, and even safer local anesthetics like lidocaine, bupivicaine, and prilocaine in the 1940s and 1950s superseded and made the use of amylocaine obsolete.

Structure
Thumb
Synonyms
  • 1-(Dimetylaminometyl)-1-metylpropyl benzoate
  • Amyléine
  • Stovaine
Product Ingredients
IngredientUNIICASInChI Key
Amylocaine hydrochloride224EF0K14Q532-59-2YCAXNWFCHTZUMD-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dentition Sirop DeSyrup180 mgDentalLab Nadeau LtÉe, Division Of Technilab Inc.1945-12-311999-09-28Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Rhino MexAmylocaine hydrochloride (.2 %) + Naphazoline hydrochloride (.1 %)LiquidNasalLaboratoires Charton Laboratories1978-12-311999-09-17Canada
Categories
UNII
QRW683O56T
CAS number
644-26-8
Weight
Average: 235.327
Monoisotopic: 235.15722892
Chemical Formula
C14H21NO2
InChI Key
FDMBBCOBEAVDAO-UHFFFAOYSA-N
InChI
InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3
IUPAC Name
1-(dimethylamino)-2-methylbutan-2-yl benzoate
SMILES
CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1

Pharmacology

Indication

The most common indication for the usage of amylocaine was spinal anesthesia [1].

Pharmacodynamics

Like all other local anesthetics, amylocaine acts as a membrane stabilizing drug that reversibly decreases the rate of depolarization and depolarization of excitable membranes [2]. In this way, the conduction of neuronal signals for certain bodily movements can be blocked [2]. In particular, when administered for spinal anesthesia, the resultant anesthesia can typically extend from the chest to the legs [2].

Mechanism of action

In particular, amylocaine, much like other local anesthetics, bind and blockade voltage gated sodium channels located in the excitable membranes of various sensory receptors [2]. Once blocked, the influx of sodium across the channels and membrane is inhibited [2]. 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 [2].

TargetActionsOrganism
AVoltage gated sodium channel
antagonist
Humans
Absorption

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 [3].

Volume of distribution

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 [3].

Protein binding

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 [3].

Metabolism

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 [3].

Route of elimination

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 [3].

Half life

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 [3].

Clearance

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 [3].

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 [3].

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Coleman RB: SPINAL ANAESTHESIA BY STOVAINE. Br Med J. 1925 Mar 21;1(3351):548-9. [PubMed:20771971]
  2. Butterworth JF 4th, Strichartz GR: Molecular mechanisms of local anesthesia: a review. Anesthesiology. 1990 Apr;72(4):711-34. [PubMed:2157353]
  3. Gary R. Strichartz (1987). Local Anesthetics. Springer, Berlin, Heidelberg. [ISBN:978-3-642-71112-1]
  4. The Wood Library-Museum: Stovaine Profile [Link]
External Links
KEGG Drug
D07454
KEGG Compound
C14169
PubChem Compound
10767
PubChem Substance
310265015
ChemSpider
10312
ChEBI
34981
ChEMBL
CHEMBL1740065
Drugs.com
Drugs.com Drug Page
Wikipedia
Amylocaine
MSDS
Download (52.5 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SyrupDental180 mg
LiquidNasal
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
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
Polarizability26.96 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Benzoyl derivatives / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzoate ester / Benzoyl / Amino acid or derivatives / Carboxylic acid ester / Tertiary aliphatic amine / Tertiary amine / Carboxylic acid derivative / Monocarboxylic acid or derivatives / Amine / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:34981)

Targets

1. Voltage gated sodium channel
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
References
  1. Butterworth JF 4th, Strichartz GR: Molecular mechanisms of local anesthesia: a review. Anesthesiology. 1990 Apr;72(4):711-34. [PubMed:2157353]

Drug created on September 15, 2015 14:30 / Updated on November 02, 2018 08:46