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Name	Prilocaine	EINECS	211-957-0
CAS No.	721-50-6	Density	1.029 g/cm³
PSA	41.13000	LogP	2.78550
Solubility	易溶于水和乙醇，略溶于氯仿	Melting Point	37-38oC
Formula	C₁₃H₂₀N₂O	Boiling Point	361.6 °C at 760 mmHg
Molecular Weight	220.315	Flash Point	134.3 °C
Transport Information	N/A	Appearance	White crystalline powder
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
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;	Article Data	8

Prilocaine Synthetic route

: 107-10-8
propylamine

: 7623-09-8
2-chloropropionyl chloride

: 95-53-4
o-toluidine

: 721-50-6
prilocaine

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In acetone Reflux;	90%

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

: 721-50-6
prilocaine

Conditions

Conditions	Yield
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

Conditions	Yield
In phosphate buffer; acetate buffer at 37℃; pH=1.14 - 7.4; Kinetics;

: 721-50-6
prilocaine

: 1786-81-8
prilocaine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate pH=1;	96%

: 887144-94-7
Togni's reagent II

: 721-50-6
prilocaine

: C14H19F3N2O

Conditions

Conditions	Yield
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

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

Prilocaine Chemical Properties

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: C₁₃H₂₀N₂O
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^-24cm³
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

Prilocaine Uses

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

Prilocaine Production

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

Prilocaine 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.

Prilocaine Safety Profile

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

Prilocaine 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.

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