Procaine hydrochloride Chemical Properties

Melting point:

155-156 °C(lit.)

Boiling point:

195-196°C 17mm

Density 

1.1761 (rough estimate)

refractive index 

1.5270 (estimate)

Flash point:

195-196°C/17mm

storage temp. 

2-8°C

form 

Crystals or Crystalline Powder

color 

Colorless to white

Water Solubility 

soluble

Sensitive 

Air Sensitive

Merck 

14,7757

BRN 

3917802

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

HCBIBCJNVBAKAB-UHFFFAOYSA-N

LogP

2.364 (est)

CAS DataBase Reference

51-05-8(CAS DataBase Reference)

EPA Substance Registry System

Procaine hydrochloride (51-05-8)

Safety Information

Hazard Codes 

T

Risk Statements 

25-43-36/37/38-23/24/25

Safety Statements 

36/37/39-45-37/39-26

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

DG2275000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29242990

Toxicity

LD50 in mice (mg/kg): 660 ± 60 s.c. (Goldenthal)

MSDS

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Procaine hydrochloride Usage And Synthesis

Description

Procaine hydrochloride, also called Novocain, or Novocaine, a topical anesthetic, which can block the nerve fiber conduction temporarilyand has a narcotic effect,strong effect, low toxicity, and non-addictive, but on the skin, mucosal penetration is weak, unsuitable for surface anesthesia, patients are used for infiltration, conduction and spinal anesthesia.
The structure of procaine hydrochloride with aromatic primary amino, easy oxidation discoloration pH, temperature, UV, oxygen and metal ions can accelerate the oxidation discoloration. The aqueous solution was stable in pH3.0~5. So preparation of procaine hydrochloride injection, it generally takes add acid to regulate pH 3.3 to 5.5, and strictly control the sterilization temperature and time. to 100 ℃ steam sterilization 30min circulation is appropriate, and should pay attention to shading, sealed save.
The above information is edited by the chemicalbook of Kui Xiongfeng.

Chemical Properties

Procaine hydrochloride is a white crystalline, odorless powder that is freely soluble in water, but less soluble in alcohol and almost insoluble in ether; solutions acid to litmus. Because the ester bond in the structure can be hydrolyzed to produce p-aminobenzoic acid and diethylaminoethanol, under certain conditions, p-aminobenzoic acid can be further decarboxylated to produce toxic aniline. Procaine hydrochloride has aromatic primary amino groups in its structure, which can be easily oxidized and discolored. pH, temperature, ultraviolet light, oxygen and metal ions can accelerate the oxidation and discoloration.

Uses

Procaine is a local anesthetic of the amino ester group that is primarily used as a topical anesthetic. Procaine is also used to control the pain of intramuscular injection of penicillin as well as in dentistry.

Definition

ChEBI: Procaine hydrochloride is an organic molecular entity.

Application

Procaine hydrochloride has been used as a component of Krebs Henseleit buffer for incubating the left ventricular cardiac tissue in its resting length. It has also been used as an inducer in M9 media for induction assay. It is a sodium channel blocker and DNA methylation inhibitor.

brand name

Novocain (Hospira).

General Description

Procaine hydrochloride is a synthetic compound that belongs to the class of local anesthetic drugs. It has a structure similar to the natural compounds that participate in nerve impulse transmission. It shows interaction with the cellular membranes causing membrane lipids to expand, membrane-bound calcium to displace and change the structure of the proteins that are responsible for regulating the cell permeability and shape.

Hazard

Toxic by ingestion.

Biochem/physiol Actions

Procaine is a Na+ channel blocker, commonly used as an anesthetic agent and is considered safer than cocaine. It is also useful as a painkiller to treat pain, associated with joints and tendons.

Contact allergens

Procaine is a local anesthetic with para-amino function. Sensitization mainly concerns the medical, dental, and veterinary professions.

Safety Profile

Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Human systemic effects: acute renal fdure. May have human reproductive effects. See also ESTERS. When heated to decomposition it emits very toxic fumes of HCl and NO,. Used as a local anesthetic.

Synthesis

The synthesis method of procaine hydrochloride is to carry out esterification reaction between p-nitrobenzoic acid and diethylaminoethanol, add Ni powder and other catalysts, and then introduce hydrogen to carry out hydrogenation reaction; this synthesis method has the characteristics of high yield, simple operation and environmental protection.

Purification Methods

Novocain is recrystallised from aqueous EtOH. It is soluble at 25o in H2O (86.3%), EtOH (2.6%) and Me2CO (1%), it is slightly soluble in CHCl3, but is almost insoluble in Et2O. The anhydrous free base is recrystallised from ligroin or Et2O and has m 61o. [Einhorn Justus Liebigs Ann Chem 371 125 1909, IR: Szymanski & Panzica J Amer Pharm Assoc 47 443 1958, Beilstein 14 IV 1138.]

Mode of action

Procaine Hydrochloride is the hydrochloride salt form of procaine, a benzoic acid derivative with local anesthetic and antiarrhythmic properties. Procaine binds to and inhibits voltage-gated sodium channels, thereby inhibiting the ionic flux required for the initiation and conduction of impulses. In addition, this agent increases electrical excitation threshold, reduces rate of rise of action potential and slows nerve impulse propagation thereby causing loss of sensation.

Precautions

Procaine hydrochloride is used for infiltration, nerve block, peridural and spinal anest sthesia. It is considered a fairly safe drug if suitable precautions are observed. However, as with any anesthetic， idiosyncrasy may be encountered. Slow administration and avoidance of accidental intravenous injection are advisable. In local administration, if increased sensitivity to procaine is suspected, as in patients with cardiac disease or endocrine disorders (such as hyperthyroidism), an initial small dose to test tolerance is recommended. (Physicians' Desk Reference, 35th ed, p. 695)

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