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51-05-8

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51-05-8 Usage

Description

Procaine hydrochloride, also known as Novocain or Novocaine, is a topical anesthetic belonging to the amino ester group. It temporarily blocks nerve fiber conduction, providing a strong effect with low toxicity and non-addictive properties. However, its weak penetration on the skin and mucosal surfaces makes it unsuitable for surface anesthesia. The chemical structure of procaine hydrochloride features an aromatic primary amino group, which is prone to oxidation discoloration influenced by pH, temperature, UV light, oxygen, and metal ions. Its aqueous solution remains stable within a pH range of 3.0 to 5.0.

Uses

Used in Medical Applications:
Procaine hydrochloride is used as a local anesthetic for infiltration, conduction, and spinal anesthesia due to its strong effect and low toxicity.
Used in Pain Management:
Procaine hydrochloride is utilized to control pain associated with intramuscular injections of penicillin, providing relief and enhancing patient comfort during treatment.
Used in Dentistry:
In the dental industry, procaine hydrochloride serves as a local anesthetic to manage pain and ensure a comfortable experience for patients during various dental procedures.
To ensure the stability and effectiveness of procaine hydrochloride, its preparation involves adding acid to regulate the pH between 3.3 and 5.5, and strictly controlling the sterilization temperature and time. Steam sterilization at 100°C for 30 minutes is considered appropriate, with attention to shading and sealed storage to prevent degradation.

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.

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)

Check Digit Verification of cas no

The CAS Registry Mumber 51-05-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 51-05:
(4*5)+(3*1)+(2*0)+(1*5)=28
28 % 10 = 8
So 51-05-8 is a valid CAS Registry Number.
InChI:InChI=1/C13H20N2O2.ClH/c1-4-15(5-2)13(3,17)12(16)10-6-8-11(14)9-7-10;/h6-9,17H,4-5,14H2,1-3H3;1H

51-05-8Synthetic route

water
7732-18-5

water

4-β-D-glucopyranosylamino-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride

4-β-D-glucopyranosylamino-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride

A

D-glucose
50-99-7

D-glucose

B

procaine hydrochloride
51-05-8

procaine hydrochloride

Conditions
ConditionsYield
at 20 - 100℃; Equilibrium constant;
sodium salicylate
54-21-7

sodium salicylate

procaine hydrochloride
51-05-8

procaine hydrochloride

procainium salicylate
4344-99-4

procainium salicylate

Conditions
ConditionsYield
In water; acetone at 20℃;98%
carbon dioxide
124-38-9

carbon dioxide

procaine hydrochloride
51-05-8

procaine hydrochloride

procainium hydrocarbonate

procainium hydrocarbonate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at -4 - 0℃; under 760.051 Torr; Product distribution / selectivity;97.7%
myricetin
529-44-2

myricetin

procaine hydrochloride
51-05-8

procaine hydrochloride

6,8-bis{p-[2-(diethylamino)ethoxycarbonyl]benzeneazo}-3,3',4',5,5',7-hexahydroxyflavone

6,8-bis{p-[2-(diethylamino)ethoxycarbonyl]benzeneazo}-3,3',4',5,5',7-hexahydroxyflavone

Conditions
ConditionsYield
Stage #1: procaine hydrochloride With hydrogenchloride; sodium acetate; sodium nitrite In water Diazotization;
Stage #2: myricetin In ethanol; water at 25℃; Substitution;
95%
procaine hydrochloride
51-05-8

procaine hydrochloride

2-diethylaminoethyl 4-amino-3-chlorobenzoate

2-diethylaminoethyl 4-amino-3-chlorobenzoate

Conditions
ConditionsYield
With N-chloro-succinimide; 2,2,6,6-tetramethylpiperidin-1-oxoammonium trifluoromethanesulfonate In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;95%
procaine hydrochloride
51-05-8

procaine hydrochloride

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

N,N'-Diethylaminoethyl-p-aminobenzoxytrimethylsilane
76064-19-2

N,N'-Diethylaminoethyl-p-aminobenzoxytrimethylsilane

Conditions
ConditionsYield
With triethylamine for 2h; Heating;82%
procaine hydrochloride
51-05-8

procaine hydrochloride

sodium 2-(4-isobutylphenyl)propionate
31121-93-4

sodium 2-(4-isobutylphenyl)propionate

C13H20N2O2*C13H18O2

C13H20N2O2*C13H18O2

Conditions
ConditionsYield
In water at 20℃; for 2h;79.1%
3-Acetyl-4,5,5-trimethyl-Δ3-butenolide
13156-10-0

3-Acetyl-4,5,5-trimethyl-Δ3-butenolide

procaine hydrochloride
51-05-8

procaine hydrochloride

4-[1-(4,5,5-Trimethyl-2-oxo-2,5-dihydro-furan-3-yl)-eth-(E)-ylideneamino]-benzoic acid 2-diethylamino-ethyl ester
82814-30-0

4-[1-(4,5,5-Trimethyl-2-oxo-2,5-dihydro-furan-3-yl)-eth-(E)-ylideneamino]-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With sodium In ethanol for 4h; Heating;54.4%
3-acetyl-2-oxo-4,5-dihydrofuran
517-23-7

3-acetyl-2-oxo-4,5-dihydrofuran

procaine hydrochloride
51-05-8

procaine hydrochloride

4-[1-(2-oxo-tetrahydro-[3]furyl)-ethylLiDenamino]-benzoic acid-(2-diethylamino-ethyl ester)

4-[1-(2-oxo-tetrahydro-[3]furyl)-ethylLiDenamino]-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
at 150℃;
D-glucose
50-99-7

D-glucose

procaine hydrochloride
51-05-8

procaine hydrochloride

4-β-D-glucopyranosylamino-benzoic acid-(2-diethylamino-ethyl ester)
47593-05-5

4-β-D-glucopyranosylamino-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
With ethanol
With water
2-Bromo-1-(3,4-dimethoxyphenyl)ethanone
1835-02-5

2-Bromo-1-(3,4-dimethoxyphenyl)ethanone

procaine hydrochloride
51-05-8

procaine hydrochloride

4-(3,4-dimethoxy-phenacylamino)-benzoic acid-(2-diethylamino-ethyl ester)

4-(3,4-dimethoxy-phenacylamino)-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
With water
p-hydroxyphenacyl chloride
6305-04-0

p-hydroxyphenacyl chloride

procaine hydrochloride
51-05-8

procaine hydrochloride

4-(4-hydroxy-phenacylamino)-benzoic acid-(2-diethylamino-ethyl ester)

4-(4-hydroxy-phenacylamino)-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
With water
procaine hydrochloride
51-05-8

procaine hydrochloride

4-amino-3-bromo-benzoic acid-(2-diethylamino-ethyl ester)

4-amino-3-bromo-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
With water; bromine
procaine hydrochloride
51-05-8

procaine hydrochloride

methyl chloroformate
79-22-1

methyl chloroformate

4-methoxycarbonylamino-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride
97441-57-1

4-methoxycarbonylamino-benzoic acid-(2-diethylamino-ethyl ester); hydrochloride

procaine hydrochloride
51-05-8

procaine hydrochloride

α-bromoacetophenone
70-11-1

α-bromoacetophenone

4-phenacylamino-benzoic acid-(2-diethylamino-ethyl ester)

4-phenacylamino-benzoic acid-(2-diethylamino-ethyl ester)

Conditions
ConditionsYield
With water
2,5,8,11,14-pentaoxa-pentadecanedioyl chloride
42021-85-2

2,5,8,11,14-pentaoxa-pentadecanedioyl chloride

procaine hydrochloride
51-05-8

procaine hydrochloride

C36H54N4O11
41562-67-8

C36H54N4O11

Conditions
ConditionsYield
With triethylamine In chloroform
benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone
87385-94-2

benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone

procaine hydrochloride
51-05-8

procaine hydrochloride

4-(4-Phenyl-2-{N'-[1-phenyl-meth-(Z)-ylidene]-hydrazino}-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester
109054-36-6

4-(4-Phenyl-2-{N'-[1-phenyl-meth-(Z)-ylidene]-hydrazino}-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, 2.) EtOH, 0-5 deg C; Yield given. Multistep reaction;
thiazolo[3,2-a]benzimidazol-3(2H)-one
3042-01-1

thiazolo[3,2-a]benzimidazol-3(2H)-one

procaine hydrochloride
51-05-8

procaine hydrochloride

4-(3-Oxo-2,3-dihydro-benzo[4,5]imidazo[2,1-b]thiazol-2-ylazo)-benzoic acid 2-diethylamino-ethyl ester; hydrochloride
107106-86-5

4-(3-Oxo-2,3-dihydro-benzo[4,5]imidazo[2,1-b]thiazol-2-ylazo)-benzoic acid 2-diethylamino-ethyl ester; hydrochloride

Conditions
ConditionsYield
With sodium nitrite 1) glacial acetic acid, H2O, 0 deg C, 2) dioxane, 2 h, 5 deg C; Yield given. Multistep reaction;
procaine hydrochloride
51-05-8

procaine hydrochloride

s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal
20432-36-4

s-trans-((2trans-4trans)-5-(4-dimethylaminophenyl)phenyl)penta-2,4-dienal

C26H33N3O2*H(1+)

C26H33N3O2*H(1+)

Conditions
ConditionsYield
With hydrogenchloride In methanol for 0.166667h;
procaine hydrochloride
51-05-8

procaine hydrochloride

2-hydroxy-benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone
109054-52-6

2-hydroxy-benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone

4-(2-{N'-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester
109081-52-9

4-(2-{N'-[1-(2-Hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, 2.) EtOH, 0-5 deg C; Yield given. Multistep reaction;
procaine hydrochloride
51-05-8

procaine hydrochloride

4-phenyl-[2-(4-metoxy-benzyliden)-hydrazinyl]-1,3-selenazole
109054-53-7

4-phenyl-[2-(4-metoxy-benzyliden)-hydrazinyl]-1,3-selenazole

4-(2-{N'-[1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester
109054-37-7

4-(2-{N'-[1-(4-Methoxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, 2.) EtOH, 0-5 deg C; Yield given. Multistep reaction;
procaine hydrochloride
51-05-8

procaine hydrochloride

4-hydroxy-3-methoxy-benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone
109054-54-8

4-hydroxy-3-methoxy-benzaldehyde (4-phenyl-selenazol-2-yl)-hydrazone

4-(2-{N'-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester

4-(2-{N'-[1-(3-Hydroxy-4-methoxy-phenyl)-meth-(Z)-ylidene]-hydrazino}-4-phenyl-selenazol-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite 1.) 0 deg C, 2.) EtOH, 0-5 deg C; Yield given. Multistep reaction;
procaine hydrochloride
51-05-8

procaine hydrochloride

3-Benzylthiazolidin-2-one-4-thione
95213-81-3

3-Benzylthiazolidin-2-one-4-thione

4-(3-Benzyl-2-oxo-4-thioxo-thiazolidin-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester; hydrochloride
117014-20-7

4-(3-Benzyl-2-oxo-4-thioxo-thiazolidin-5-ylazo)-benzoic acid 2-diethylamino-ethyl ester; hydrochloride

Conditions
ConditionsYield
With sodium nitrite 1.) acetic acid, water, 0-5 deg C, 10 min, 2.) dioxane, 0 deg C, 2 h; Yield given. Multistep reaction;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Carbamoyl-2-methoxy-benzoyl chloride
60795-47-3

5-Carbamoyl-2-methoxy-benzoyl chloride

4-(5-Carbamoyl-2-methoxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-52-9

4-(5-Carbamoyl-2-methoxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Carbamoyl-2-octyloxy-benzoyl chloride

5-Carbamoyl-2-octyloxy-benzoyl chloride

4-(5-Carbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-50-7

4-(5-Carbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

2-Methoxy-5-octylcarbamoyl-benzoyl chloride

2-Methoxy-5-octylcarbamoyl-benzoyl chloride

4-(2-Methoxy-5-octylcarbamoyl-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-60-9

4-(2-Methoxy-5-octylcarbamoyl-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Isopropylcarbamoyl-2-octyloxy-benzoyl chloride

5-Isopropylcarbamoyl-2-octyloxy-benzoyl chloride

4-(5-Isopropylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-57-4

4-(5-Isopropylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Isobutylcarbamoyl-2-octyloxy-benzoyl chloride

5-Isobutylcarbamoyl-2-octyloxy-benzoyl chloride

4-(5-Isobutylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-51-8

4-(5-Isobutylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Cyclohexylcarbamoyl-2-octyloxy-benzoyl chloride

5-Cyclohexylcarbamoyl-2-octyloxy-benzoyl chloride

4-(5-Cyclohexylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-53-0

4-(5-Cyclohexylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

5-Octylcarbamoyl-2-octyloxy-benzoyl chloride

5-Octylcarbamoyl-2-octyloxy-benzoyl chloride

4-(5-Octylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester
89366-59-6

4-(5-Octylcarbamoyl-2-octyloxy-benzoylamino)-benzoic acid 2-diethylamino-ethyl ester

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 3h; Heating; Yield given;
procaine hydrochloride
51-05-8

procaine hydrochloride

Procainperiodid

Procainperiodid

Conditions
ConditionsYield
With iodine; potassium iodide In ethanol

51-05-8Upstream product

51-05-8Relevant articles and documents

CARDIOPLEGIC SOLUTION

-

, (2011/02/18)

The present invention relates to a new cardioplegic solution to arrest and protect the heart muscle during surgery. The cardioplegic solution according to the invention offers several significant advantages as compared to standard available solutions, and contains magnesium sulfate heptahydrate, potassium chloride, procaine hydrochloride and xylitol.