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Prilocaine

Local anesthetic drug Chemical Properties Uses Production method
Prilocaine
Prilocaine structure
CAS No.
721-50-6
Chemical Name:
Prilocaine
Synonyms
l67;L 67;Priloca;Citanest;astra1512;astra1515;NSC 40027;Astra 1512;Astra 1515;PRILOCAINE
CBNumber:
CB8270843
Molecular Formula:
C13H20N2O
Formula Weight:
220.31
MOL File:
721-50-6.mol

Prilocaine Properties

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
storage temp. 
2-8°C
solubility 
Slightly soluble in water, very soluble in acetone and in ethanol (96 per cent).
form 
neat
pka
pKa 7.32 or 7.89 (Uncertain)
Water Solubility 
6.169g/L(25 ºC)
InChIKey
MVFGUOIZUNYYSO-UHFFFAOYSA-N
CAS DataBase Reference
721-50-6(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
046O35D44R
NCI Drug Dictionary
Citanest
ATC code
N01BB04,N01BB54
NIST Chemistry Reference
Propanamide, n-(2-methylphenyl)-2-(propylamino)-(721-50-6)
SAFETY
  • Risk and Safety Statements
HS Code  2924296000

Prilocaine price More Price(3)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P2939000 Prilocaine European Pharmacopoeia (EP) Reference Standard 721-50-6 p2939000 $190 2020-08-18 Buy
Sigma-Aldrich P2939000 Prilocaine European Pharmacopoeia (EP) Reference Standard 721-50-6 $190 2021-03-22 Buy
Sigma-Aldrich 1560990 Prilocaine United States Pharmacopeia (USP) Reference Standard 721-50-6 200mg $366 2021-03-22 Buy

Prilocaine Chemical Properties,Uses,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.
the structural formula of prilocaine
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.

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.

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.

Chemical 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

Preparation Products


Prilocaine Suppliers

Global( 280)Suppliers
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Jinan Jianfeng Chemical Co., Ltd
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Frapp's ChemicalNFTZ Co., Ltd.
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Beijing Cooperate Pharmaceutical Co.,Ltd
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View Lastest Price from Prilocaine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-04 Prilocaine BASE
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-12-04 Prilocaine
721-50-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-12-04 Prilocaine
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

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