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Articaine hydrochloride

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Articaine hydrochloride Basic information

Product Name:
Articaine hydrochloride
Synonyms:
  • methyl 4-methyl-3-[[(1-oxo-2-(propylamino)propyl]amino]-2-thenoate monohydrochloride
  • CarticaineHCl
  • Ultracaine
  • CARTICAINE HYDROCHLORIDE
  • Ultracain
  • Articaine hydrochloride
  • Methyl 4-methyl-3-(2-propylaminopropanoylamino)thiophene-2-carboxylate hydrochloride
  • Articaine Hydrochloride (125 mg)
CAS:
23964-57-0
MF:
C13H20N2O3S.ClH
MW:
320.839
EINECS:
245-957-7
Product Categories:
  • API
  • research chemical
  • local anesthetic
  • Pharmaceutical intermediate
  • BDO
Mol File:
23964-57-0.mol
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Articaine hydrochloride Chemical Properties

Melting point:
177-178°
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
H2O: soluble20mg/mL, clear
form 
powder
color 
white to beige
Stability:
Hygroscopic
InChI
InChI=1S/C13H20N2O3S.ClH/c1-5-6-14-9(3)12(16)15-10-8(2)7-19-11(10)13(17)18-4;/h7,9,14H,5-6H2,1-4H3,(H,15,16);1H
InChIKey
GDWDBGSWGNEMGJ-UHFFFAOYSA-N
SMILES
C1(NC(=O)C(C)NCCC)C(C)=CSC=1C(=O)OC.Cl
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
2934990002
Toxicity
LD50 i.v. in mice: 37 mg/kg (Muschaweck, Rippel)
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Articaine hydrochloride Usage And Synthesis

Description

Articaine hydrochloride is a thiophene-containing local anesthetic pharmacologically similar to mepivacaine. Most local anesthetics act by abolishing voltage-gated sodium channel currents indiscriminately in all populations of neurons. Articaine is an amide local anesthetic most commonly used in dentistry. It possesses a unique ester side chain that is metabolized rapidly by circulating esterases. Articaine is reported to modify cardiac action potentials and ion currents only at concentrations higher than the therapeutic range needed to inhibit voltage-gated sodium channels.

Chemical Properties

White or almost white, crystalline powder.

Originator

Ultracain,Hoechst,W. Germany,1976

Uses

Articaine hydrochloride, belonging to the group of amide anesthetics, is a local anesthetic with a short duration of action. It is utilized for regional anesthesia in day-case surgeries such as arthroscopy, hand and foot surgery, and dentistry.

Manufacturing Process

3-α-Chloropropionylamino-2-carbomethoxy-4-methylthiophene (prepared from 3-amino-2-carbomethoxy-4-methylthiophene and chloropropionyl chloride) was dissolved in toluene and n-propylamine added. The whole mixture was heated to boiling for 6 to 7 hours. After cooling, the propylamine hydrochloride that had formed was removed by washing with water, The toluene phase was dried with sodium sulfate, and then the solvent and excess propylamine were removed by distillation. The oily residue was taken up in ether. The hydrochloride of 3-n-propylamino-α-propionylamino-2- carbomethoxy-4-methylthiophene was obtained by introducing hydrogen chloride gas or by means of methanolic hydrogen chloride. The base boils at 162°C to 167°C under 0.3 mm of mercury pressure and the hydrochloride melts at 177°C to 178°C.

brand name

Septanest (Cilag-Chemie, Switzerland); Septocaine (Cilag-Chemie, Switzerland); Ultracaine (Hoechst AG, Germany).

Therapeutic Function

Local anesthetic

Contact allergens

This local amide-type anesthetic is seldom reported as allergenic even in patients sensitized to other amidetype molecules like lidocaine, prilocaine, mepivacaine, or bupivacaine.

Biochem/physiol Actions

Articaine hydrochloride helps to alleviate pain and blocks transmission of the pain signal. Articaine is an amide local anesthetic widely used in dentistry. Articaine acts by inhibition of nerve impulse conduction by blockade of sodium channels.

Metabolism

Articaine is the only amide local anesthetic containing a thiophene aromatic ring rather than benzene. Because articaine hydrochloride is the only widely used amide local anesthetic that also contains an ester group, biotransformation of articaine hydrochloride occurs in both plasma (hydrolysis by plasma esterase—similarly to other ester local anesthetics) and liver (hepatic microsomal enzymes—similarly to other amide local anesthetics). The metabolism of articaine hydrochloride is initiated by hydrolysis of the carboxylic acid ester groups to obtain free carboxylic acid. Its primary metabolite, articainic acid, is pharmacologically inactive, undergoing additional biotransformation to form articainic acid glucuronide. Additional metabolites have been detected in animal studies. From this point, the reaction can follow several pathways: cleavage of carboxylic acid, formation of an acid amino group by internal cyclization, and oxidation.

Mode of action

Articaine Hydrochloride is the hydrochloride salt form of articaine, an amide-type local anesthetic. Its mechanism of action involves reversible blockage of nerve impulse conduction through binding to specific sodium ion channels on the membrane, thereby interfering with the electrical excitation in the nerve, slowing the propagation of the nerve impulse and reducing the rate of action potential rise. This results in a loss of sensation at the site of injection. Articaine hydrochloride is used for relief of pain in minor operations, usually in combination with the vasoconstrictor epinephrine.

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