Local anesthetic drug Chemical Properties Uses Production method
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Prilocaine

Local anesthetic drug Chemical Properties Uses Production method
Product Name
Prilocaine
CAS No.
721-50-6
Chemical Name
Prilocaine
Synonyms
PRILOCAINE BASE;Aβ25-35;Citanest;Propitocaine;l67;N-(2-methylphenyl)-2-(propylamino)propionamide;L 67;Priloca;astra1512;astra1515
CBNumber
CB8270843
Molecular Formula
C13H20N2O
Formula Weight
220.31
MOL File
721-50-6.mol
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Prilocaine Property

Melting point:
37-38°
Boiling point:
bp0.1 159-162°
Density 
1.0117 (rough estimate)
refractive index 
nD20 1.5298
storage temp. 
2-8°C
solubility 
Slightly soluble in water, very soluble in acetone and in ethanol (96 per cent).
pka
pKa 7.32 or 7.89 (Uncertain)
form 
Solid
color 
White to off-white
Water Solubility 
6.169g/L(25 ºC)
InChI
InChI=1S/C13H20N2O/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2/h5-8,11,14H,4,9H2,1-3H3,(H,15,16)
InChIKey
MVFGUOIZUNYYSO-UHFFFAOYSA-N
SMILES
C(NC1=CC=CC=C1C)(=O)C(NCCC)C
CAS DataBase Reference
721-50-6(CAS DataBase Reference)
NIST Chemistry Reference
Propanamide, n-(2-methylphenyl)-2-(propylamino)-(721-50-6)
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Safety

HS Code 
2924296000
Hazardous Substances Data
721-50-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR3105
Product name
Prilocaine
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$182
Updated
2024/03/01
Sigma-Aldrich
Product number
P2939000
Product name
Prilocaine
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
p2939000
Price
$220
Updated
2024/03/01
Sigma-Aldrich
Product number
1560990
Product name
Prilocaine
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$186.4
Updated
2024/03/01
TRC
Product number
P725005
Product name
Prilocaine
Packaging
5mg
Price
$195
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0005904
Product name
PRILOCAINE
Purity
95.00%
Packaging
1G
Price
$186.9
Updated
2021/12/16
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Prilocaine Chemical Properties,Usage,Production

Local anesthetic drug

Prilocaine belongs to amide local anesthetic drug with its anesthesia intensity and speed being similar as lidocaine but with a longer duration period and weaker effect on vasodilation. It has a lower toxicity than lidocaine. It is clinically for local anesthesia, especially suitable for treating patients who are not allowed to use adrenaline.
[Pharmacological] its 3% solution has a similar local anesthesia efficacy as the anesthesia drug of 2% lidocaine together with adrenaline. It has a slow onset time which lasts about 6~7min and the duration time of about 1.5~2h. It has a strong penetration capability through mucous membranes. Adrenaline has a slightly prolonged duration of action. PPB is 55% and T1/2 of about 1.5h. It is subject to liver metabolism with its metabolites nitroso toluidine being able to oxidize hemoglobin to form methemoglobin. It can be transported to the fetus through the placenta.
[Adverse reactions] once the usage amount exceeds 600mg, methaemoglobinaemia can occur with cyanosis, tachycardia, headache, dizziness and weakness occurring.
[Note] patients of anemia, congenital or acquired methaemoglobinaemia, respiratory failure or heart failure and hypoxic patients should be disabled. It is forbidden for applied to obstetric anesthesia.
[Usage and dosage] infiltration anesthesia: 0.5% to 1% solution with the duration of action of 1 to 1.5 hours.
Nerve blocking anesthesia: use 1% to 2% solution with the duration of action being 2-3 hours.
Epidural anesthesia: use10 to 30 mL of 1.5%~1% solution with the duration of action of 2.5 to 3.5 hours. Use a maximum dose of 600 mg.

Figure 1 the structural formula of prilocaine
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chemical Properties

It is a kind of needle-like crystals with the melting point being 37-38 ℃ and the boiling point being 159-162 ℃ (0.133kPa), and refractive index (nD20) being 1.5299. Its hydrochloride ([1786-81-8]) is a white crystalline powder. The Melting point is 167-168 ℃. It is soluble in water and ethanol, slightly soluble in chloroform. It has sour taste and bitter taste and is odorless.

Uses

It is a kind of local anesthetic drug. The product has better efficacy than procaine and the local anesthesia intensity and speed being similar as lidocaine but with longer duration time and less toxicity as well as smaller accumulation effect. It is suitable for epidural anesthesia, conduction anesthesia and infiltration anesthesia.

Production method

O-toluidine and α-bromo-propionyl bromide are condensed and further have reaction with propylamine obtain prilocaine.

Chemical Properties

White or almost white, crystalline powder.

Uses

Prilocaine is a local anesthetic of the amino amide type. Prilocaine is often used in dentistry. Prilocaine is also often combined with lidocaine as a preparation for dermal anesthesia (lidocaine/prilocaine or EMLA), for treatment of conditions like paresthesia.

Uses

In terms of pharmacological parameters, prilocaine is comparable to lidocaine; however, because of a number of toxic manifestations, it is rarely used in medical practice. Citanest and xylonest are well-known synonyms for prilocaine.

Definition

ChEBI: An amino acid amide in which N-propyl-DL-alanine and 2-methylaniline have combined to form the amide bond; used as a local anaesthetic.

brand name

lidocaine/prilocaine topical
Brand names: Emla, LiproZonePak, Dolotranz, Livixil Pak, and Anodyne LPT.

General Description

Prilocaine hydrochloride is a water-soluble salt available asa solution for nerve block or infiltration in dental procedures.Prilocaine is used for intravenous regional anesthesiaas the risk of CNS toxicity is low because of the quick metabolism.Prilocaine prepared in the crystal form is used inEMLA for topical administration to decrease painful needlesticks in children. Prilocaine 4% solution should be protectedfrom light and the manufacturer recommends discardingif the solution turns pinkish or slightly darker than lightyellow. Solutions are available in various concentrations upto 4%, with or without epinephrine and with or withoutpreservatives.

Pharmacology

Prilocaine is less toxic than lidocaine, with a high clearance, attributable to metabolism in the lungs, kidneys and liver. It is associated with methaemoglobinaemia at doses >600mg. It is sometimes used at a concentration of 0.5% for the provision of intravenous regional anaesthesia, and a combination of prilocaine 3% with felypressin is available for low-volume local infiltration anaesthesia in dental surgery. A 2% formulation is also available for spinal anaesthesia. Prilocaine is also formulated in a eutectic mixture with lidocaine (EMLA) for topical anaesthesia.

Clinical Use

Prilocaine metabolism has beenstudied extensively in animal models, less is known aboutthe human metabolites or the human CYP enzymes involvedin their formation . The metabolism of prilocainein the liver yields o-toluidine, which is a possiblecarcinogen. Many aromatic amines, including o-toluidinehave been shown to be mutagenic, and metabolites of otoluidinehave been shown to form DNA adducts.Metabolites of o-toluidine are also believed to be responsiblefor the methemoglobinemia observed with prilocaineuse. To decrease the potential for methemoglobinemia, strictadherence to the maximum recommended dose should befollowed. Metabolism of prilocaine is extensive with lessthan 5% of a dose excreted unchanged in the urine.

Synthesis

Prilocaine, 2-(propylamino)-o-propiontoluidine (2.2.14), is structurally related to the exact same group as ethidocaine, yet it differs structurally in that during synthesis, o-toluidine is used instead of 2,6-dimethylaniline, and instead of a butyric acid, a fragment of propionic acid, and a terminal propylethylamine group is replaced with a propylamine group. In order to synthesize prilocaine, o-toluidine is reacted with bromopropionyl bromide, and the resulting bromopropionyltoluidide (2.2.13) is then reacted with propylamine, which gives prilocaine [22,23].

Prilocaine Preparation Products And Raw materials

Raw materials

Propionyl bromide o-Toluidine Propylamine

Preparation Products

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View Lastest Price from Prilocaine manufacturers

Dorne Chemical Technology co. LTD
Product
Prilocaine 721-50-6
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-03-26
Jinan Million Pharmaceutical Co., Ltd
Product
Prilocaine 721-50-6
Price
US $2.00/kg
Min. Order
0.10000000kg
Purity
99%
Supply Ability
200KG
Release date
2024-07-23
Hebei Miaoyin Technology Co.,Ltd
Product
Prilocaine 721-50-6
Price
US $50.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
10000 Kilogram/Kilograms per Day
Release date
2023-03-10

721-50-6, PrilocaineRelated Search:

Propylamine Isopropylamine (-)-2-[METHYLAMINO]-1-PHENYLPROPANE Propitocaine hydrochloride Allylamine D/L-AMPHETAMINE HYDROCHLORIDE PRILOCAINE IMPURITY E Propionamide PRILOCAINE RELATED COMPOUND B (50 MG) ((RS)-N-(4-METHYLPHENYL)-2-(PROPYLAMINO)PROPANA-MIDE) (R)-Prilocaine,D-(-)-Prilocaine (S)-Prilocaine,L-(+)-Prilocaine Prilocaine PRILOCAINE HCL USP(CRM STANDARD) MIXTUREOFAMYLOCAINE,LIGNOCAINE,PRILOCAINE PRILOCAINE HYDROCHLORIDE IMP. B (EP): 2-METHYLBENZENAMINE (O-TOLUIDINE) PRILOCAINE IMPURITY E(RS)-N-(METHYLPHENYL)-2-(PROPYLAMINO)PROPANAMIDE EPP(CRM STANDARD) prilocaine-phenylephrine

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