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High Quality 99% Prilocaine 721-50-6 GMP manufacturer
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Local Anesthesia Prilocaine Powder 721-50-6 to Numb Tissues CAS NO.721-50-6
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CAS:721-50-6 Prilocaine
Cas No: 721-50-6
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721-50-6 Usage

Chemical Properties

White or almost white, crystalline powder.

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.

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.

Production method

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

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 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.

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].

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.

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.

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.
InChI:InChI=1/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)

721-50-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name prilocaine

1.2 Other means of identification

Product number -
Other names Citanest

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:721-50-6 SDS

721-50-6Synthetic route

propylamine
107-10-8

propylamine

2-chloropropionyl chloride
7623-09-8

2-chloropropionyl chloride

o-toluidine
95-53-4

o-toluidine

prilocaine
721-50-6

prilocaine

Conditions
ConditionsYield
Stage #1: 2-chloropropionyl chloride; o-toluidine With potassium carbonate In acetone at 0 - 30℃; for 5h;
Stage #2: propylamine In acetone at 70℃; for 14h;
97%
propylamine
107-10-8

propylamine

N-(2-methylphenyl)-2-chloropropanamide
19281-31-3

N-(2-methylphenyl)-2-chloropropanamide

prilocaine
721-50-6

prilocaine

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;90%
5-methyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride

5-methyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride

prilocaine
721-50-6

prilocaine

Conditions
ConditionsYield
In phosphate buffer; acetate buffer at 60℃; pH=2.15 - 7.4; Kinetics;
2,5-dimethyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride

2,5-dimethyl-1-propyl-3-o-tolyl-imidazolidin-4-one; hydrochloride

prilocaine
721-50-6

prilocaine

Conditions
ConditionsYield
In phosphate buffer; acetate buffer at 37℃; pH=1.14 - 7.4; Kinetics;
prilocaine
721-50-6

prilocaine

prilocaine hydrochloride
1786-81-8

prilocaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=1;96%
Togni's reagent II
887144-94-7

Togni's reagent II

prilocaine
721-50-6

prilocaine

C14H19F3N2O

C14H19F3N2O

Conditions
ConditionsYield
With sodium decatungstate; sulfuric acid; copper dichloride In water; acetonitrile at 20 - 30℃; for 12h; Irradiation; regioselective reaction;63%
prilocaine
721-50-6

prilocaine

(+)-Prilocaine

(+)-Prilocaine

prilocaine
721-50-6

prilocaine

(-)-Prilocaine

(-)-Prilocaine

prilocaine
721-50-6

prilocaine

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

C42H70O35*C13H20N2O
521964-99-8

C42H70O35*C13H20N2O

Conditions
ConditionsYield
In methanol at 20℃; for 24h;

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