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721-50-6

Basic Information
CAS No.: 721-50-6
Name: Prilocaine
Article Data: 8
Molecular Structure:
Molecular Structure of 721-50-6 (Prilocaine)
Formula: C13H20N2O
Molecular Weight: 220.315
Synonyms: o-Propionotoluidide,2-(propylamino)- (6CI,8CI);2-Methyl-a-propylaminopropionanilide;Astra 1512;Astra 1515;Citanest;N-(2,6-Dimethylphenyl)-2-(propylamino)propanamide;NSC 40027;Propitocaine;o-Methyl-2-propylaminopropionanilide;
EINECS: 211-957-0
Density: 1.029 g/cm3
Melting Point: 37-38oC
Boiling Point: 361.6 °C at 760 mmHg
Flash Point: 134.3 °C
Solubility: 易溶于水和乙醇,略溶于氯仿
Appearance: White crystalline powder
PSA: 41.13000
LogP: 2.78550
Synthetic route
107-10-8

propylamine

7623-09-8

2-chloropropionyl chloride

95-53-4

o-toluidine

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%
107-10-8

propylamine

19281-31-3

N-(2-methylphenyl)-2-chloropropanamide

721-50-6

prilocaine

Conditions
ConditionsYield
With potassium carbonate In acetone Reflux;90%

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

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

721-50-6

prilocaine

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

prilocaine

1786-81-8

prilocaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate pH=1;96%
887144-94-7

Togni's reagent II

721-50-6

prilocaine

C14H19F3N2O

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

prilocaine

(+)-Prilocaine

721-50-6

prilocaine

(-)-Prilocaine

721-50-6

prilocaine

7585-39-9

β‐cyclodextrin

521964-99-8

C42H70O35*C13H20N2O

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

Molecule structure of Propanamide, N-(2-methylphenyl)-2-(propylamino)- (CAS NO.721-50-6):

IUPAC Name: N-(2-Methylphenyl)-2-(propylamino)propanamide 
Molecular Weight: 220.3107 g/mol
Molecular Formula: C13H20N2
Density: 1.029 g/cm3 
Melting Point: 37-38 deg C
Boiling Point: 361.6 °C at 760 mmHg 
Flash Point: 134.3 °C
Index of Refraction: 1.542
Molar Refractivity: 67.43 cm3
Molar Volume: 214 cm3
Polarizability: 26.73×10-24 cm3
Surface Tension: 38.5 dyne/cm 
Enthalpy of Vaporization: 60.74 kJ/mol
Vapour Pressure: 2.05E-05 mmHg at 25 °C 
log P (octanol-water): 2.11
Water Solubility: 541 mg/L
XLogP3: 2.1
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 5
Tautomer Count: 2
Exact Mass: 220.157563
MonoIsotopic Mass: 220.157563
Topological Polar Surface Area: 41.1
Heavy Atom Count: 16
Complexity: 218
Canonical SMILES: CCCNC(C)C(=O)NC1=CC=CC=C1C
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
EINECS: 211-957-0
Product Categories: Active Pharmaceutical Ingredients

Uses

 Propanamide, N-(2-methylphenyl)-2-(propylamino)- (CAS NO.721-50-6) is used as local anesthetics.

Production

After the condensation reaction of O-toluidine and α-bromo-propionyl bromide, add propylamine to obtaine the product.

Toxicity Data With Reference

 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 231mg/kg (231mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 455, 1965.
mouse LD50 intravenous 59900ug/kg (59.9mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 455, 1965.
mouse LD50 subcutaneous 519mg/kg (519mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 61, Pg. 455, 1965.

Safety Profile

Hazardous Substances Data: 721-50-6(Hazardous Substances Data)

Specification

 Propanamide, N-(2-methylphenyl)-2-(propylamino)- (CAS NO.721-50-6) is also named as 2-(Propylamino)-o-propionotoluidide ; 2-Methyl-alpha-propylaminopropionanilide ; Astra 1515 ; BRN 2108498 ; Citanest ; HSDB 3386 ; N-(2-Methylphenyl)-2-(propylamino)propanamide ; NSC 40027 ; Prilocaina ; Prilocaina [INN-Spanish] ; Prilocaine ; Prilocainum ; Prilocainum [INN-Latin] ; Propitocaine ; UNII-046O35D44R ; alpha-n-Propylamino-2-methylpropionanilide ; o-Methyl-2-propylaminopropionanilide ; o-Methyl-alpha-propylaminopropionanilide ; o-Propionotoluidide, 2-propylamino- . Propanamide, N-(2-methylphenyl)-2-(propylamino)- (CAS NO.721-50-6) is needle crystal with sour bitter taste and odorless. It is soluble in water and ethanol and a little soluble in chloroform.