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Amylocaine

HCID 10767
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Basic information

CAS
644-26-8
Standard SMILES
CCC(C)(CN(C)C)OC(=O)c1ccccc1
InChIKey
FDMBBCOBEAVDAO-UHFFFAOYSA-N
Molecular formula
C14H21NO2
Average molar mass
235.32 g/mol
Monoisotopic mass
235.15722891

Overview

Stovaine is a benzoate ester.

Names & identifiers

Preferred name
Amylocaine
IUPAC
[1-(dimethylamino)-2-methylbutan-2-yl] benzoate
English name
1-[(dimethylamino)methyl]-1-methylpropyl benzoate
Molecular formula
C14H21NO2
Molecular weight
235.32

Names & synonyms

AmylocaineStovaine644-26-8QRW683O56T1-(DIMETHYLAMINO)-2-METHYL-2-BUTANOL BENZOATEDTXSID6047862(1-((dimethylamino)methyl)-1-methyl-propyl) benzoate[1-[(dimethylamino)methyl]-1-methyl-propyl] benzoateRefChem:557965DTXCID2027838211-411-1Amyleine
Show more names
Stovain2-Butanol, 1-(dimethylamino)-2-methyl-, 2-benzoateBenzoic acid 1-[(dimethylamino)methyl]-1-methylpropyl ester
Amylocaine [BAN]1-(Dimethylamino)-2-methylbutan-2-yl benzoate[1-(dimethylamino)-2-methylbutan-2-yl] benzoateEINECS 211-411-1Amylocaine (BAN)1-[(Dimethylamino)methyl]-1-methylpropyl benzoate1-((Dimethylamino)methyl)-1-methylpropyl benzoate2-Butanol, 1-(dimethylamino)-2-methyl-, benzoate

Database identifiers

CAS
644-26-8
PubChem CID
10767
DTXSID
DTXSID6047862
ChEMBL
CHEMBL1740065
ChEBI
CHEBI:34981
UNII
QRW683O56T
EC Number
211-411-1
Nikkaji
J13.802I

Properties

Computed structural properties

XLogP
3
Topological polar surface area
29.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
17
Formal charge
0
Complexity
247

Experimental & physicochemical properties

Human DrugsPharmaceuticals

Physicochemical properties

Boiling point
377.72 °C · 377.72°C (rough estimate)
Density
1.0247 · 1.0247 (rough estimate)
refractive index
1.5385 · 1.5385 (estimate)
FDA UNII
683 O56T · QRW683O56T
Toxicity
25 mg/kg · LDLo ivn-rat: 25 mg/kg PHREA7 12,262,32

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

Toxicity
LDLo ivn-rat: 25 mg/kg PHREA7 12,262,32

Chemistry & industry

Pharmacology

Protein BindingA 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.
Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Biological Half-LifeA 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.
Metabolism/MetabolitesA 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.
Absorption, Distribution and Excretion · 4 items

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.

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Compound notes

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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.

Uses & manufacturing

Use ClassificationPharmaceuticals

Applications

UsesAmylocaine is a local agent that can suppress or relieve pain of the ester type. Amylocaine can cause reversible insensitization near the area where it is administered. Amylocaine is used mostly in spinal anesthesia[1].

Upstream & downstream products

Upstream raw materials

1-Chloro-2-methyl-2-butanol

Additional notes

DefinitionChEBI: Stovaine is a benzoate ester.