Procaine

Overview

Procaine is a local anesthetic drug of the amino ester group. It is most commonly used in dental procedures to numb the area around a tooth and is also used to reduce the pain of intramuscular injection of penicillin. Owing to the ubiquity of the trade name Novocain (without the "e" in the original German patent) or Novocaine (with the "e" in the US patent), in some regions, procaine is referred to generically as novocaine. It acts mainly as a sodium channel blocker. Today, it is used therapeutically in some countries due to its sympatholytic, anti-inflammatory, perfusion-enhancing, and mood-enhancing effects.[1][2][3] WP⚠ Wikipedia itself has flagged this text: failed verification.

Procaine was first synthesized in 1905, shortly after amylocaine. It was created by the chemist Alfred Einhorn who gave the chemical the trade name Novocain, from the Latin nov- (meaning "new") and -caine, a common ending for alkaloids used as anesthetics. It was introduced into medical use by surgeon Heinrich Braun.[4][5] WP

Prior to the discovery of amylocaine and procaine, cocaine was a commonly used local anesthetic. Einhorn wished his new discovery to be used for amputations, but for this surgeons preferred general anesthesia. Dentists, however, found it very useful.[6][7] WP

Risks and side effects

Adverse effects

Application of procaine leads to the depression of neuronal activity. The depression causes the nervous system to become hypersensitive, producing restlessness and shaking, leading to minor to severe convulsions. Studies on animals have shown the use of procaine led to the increase of dopamine and serotonin levels in the brain. Other issues may occur because of varying individual tolerance to procaine dosage. Nervousness and dizziness can arise from the excitation of the central nervous system, which may lead to respiratory failure if overdosed. Procaine may also induce weakening of the myocardium, leading to cardiac arrest.[8][9] WP⚠ Wikipedia itself has flagged this text: citation needed.

Procaine can also cause allergic reactions causing individuals to have problems with breathing, rashes, and swelling. Allergic reactions to procaine are usually not in response to procaine itself, but to its metabolite PABA. Allergic reactions are in fact quite rare, estimated to have an incidence of 1 per 500,000 injections. About one in 3000 white North Americans is homozygous (i.e. has two copies of the abnormal gene) for the most common atypical form of the enzyme pseudocholinesterase, and do not hydrolyze ester anesthetics such as procaine. This results in a prolonged period of high levels of the anesthetic in the blood and increased toxicity.[10][11] WP

However, certain populations in the world such as the Vysya community in India commonly have a deficiency of this enzyme.[11] WP

Pharmacology

Pharmacodynamics

The primary use for procaine is as an anaesthetic. WP

Aside from its use as a dental anesthetic, procaine is used less frequently today, since more effective (and hypoallergenic) alternatives such as lidocaine (Xylocaine) exist. Like other local anesthetics (such as mepivacaine, and prilocaine), procaine is a vasodilator, thus is often coadministered with epinephrine for the purpose of vasoconstriction. Vasoconstriction helps to reduce bleeding, increases the duration and quality of anesthesia, prevents the drug from reaching systemic circulation in large amounts, and overall reduces the amount of anesthetic required. As a dental anesthesic, for example, more novocaine is needed for root canal treatment than for a simple filling. Unlike cocaine, a vasoconstrictor, procaine does not have the euphoric and addictive qualities that put it at risk for abuse.[1][12] WP

Procaine is also a DNA-demethylating agent with growth-inhibitory effects in human cancer cells.[13] WP

A 1% procaine injection has been recommended for the treatment of extravasation complications associated with venipuncture, steroids, and antibiotics. It has likewise been recommended for treatment of inadvertent intra-arterial injections (10 ml of 1% procaine), as it helps relieve pain and vascular spasm. WP

Procaine is an occasional additive in illicit street drugs and is presented and sold usually as cocaine or heroin.[14] WP

Pharmacokinetics

Procaine, an ester anesthetic, is metabolized in the plasma by the enzyme pseudocholinesterase through hydrolysis into para-amino benzoic acid (PABA), which is then excreted by the kidneys into the urine. WP

Chemistry

Formula

C13H20N2O2 PC

CAS number

59-46-1 PC

Molar mass (g/mol)

236.31 PC

IUPAC name (computed by PubChem)

2-(diethylamino)ethyl 4-aminobenzoate PC

SMILES

CCN(CC)CCOC(=O)C1=CC=C(C=C1)N PC

InChIKey

MFDFERRIHVXMIY-UHFFFAOYSA-N PC

PubChem CID

4914

IUPAC name

2-(diethylamino)ethyl 4-aminobenzoate WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other How long does numbness last after the dentist?. May 22, 2018
2. Harm reduction site Procaine (DB00721). 2009-06-23
3. Journal / agency Hahn-Godeffroy JD. Procain-Reset: Ein Therapiekonzept zur Behandlung chronischer Erkrankungen. Schweizerische Zeitschrift für Ganzheitsmedizin. 2011. doi:10.1159/000332021
4. Other Ritchie JM, Greene NM. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 1990
5. Other Minard R. The Preparation of the Local Anesthetic, Benzocaine, by an Esterification Reaction. 18 October 2006
6. Journal / agency Ruetsch YA, Böni T, Borgeat A. From cocaine to ropivacaine: the history of local anesthetic drugs. Current Topics in Medicinal Chemistry. August 2001. doi:10.2174/1568026013395335 · PMID 11895133
7. Journal / agency Drucker P. The discipline of innovation. Harvard Business Review. May 1985. PMID 10272260
8. Journal / agency Sawaki K, Kawaguchi M. Some correlations between procaine-induced convulsions and monoamines in the spinal cord of rats. Japanese Journal of Pharmacology. November 1989. doi:10.1254/jjp.51.369 · PMID 2622091
9. Other Novocain Official FDA information. August 2007
10. Journal / agency Ombregt, Ludwig. A System of Orthopaedic Medicine. 2013. doi:10.1016/B978-0-7020-3145-8.00005-3
11. Other Butyrylcholinesterase
12. Journal / agency Sisk AL. Vasoconstrictors in local anesthesia for dentistry. Anesthesia Progress. 1992. PMID 8250339 · PMC2148619
13. Journal / agency Villar-Garea A, Fraga MF, Espada J, Esteller M. Procaine is a DNA-demethylating agent with growth-inhibitory effects in human cancer cells. Cancer Research. 2003. PMID 12941824
14. Other Procaine

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