18 May 2020

Cocaine – a tropane alkaloid

NATURAL TOXIN

Cocaine is a powerful central nervous system stimulant and local anesthetic activity.

Cocaine is a naturally occurring tropane alkaloid extracted from the leaves of an Andean shrub, Erythroxylum coca. In 1880s, cocaine was used for local surgeries as an anesthetic agent, but later it becomes recreational drug (since 1970s). In 2016, the total number of cocaine user was estimated to be 18.2 million Worldwide, of which 20% resided in Western and Central Europe. Cocaine is structurally related to atropine (hyoscamine) and hyoscine (scopolamine), substances with quite different pharmacological properties.

Cacaine

Figure: (a) Erythroxylum coca, (b) cocaine powder and (c) chemical structure of cocaine.

Cocaine stimulates the sympathetic nervous system by inhibiting reuptake of norepinephrine, dopamine, and serotonin by interacting with each transporter, leading to exaggerated, prolonged sympathetic nervous system activity. It exerts its local anesthetic effects in the neuronal cell membrane by binding to and blocking the voltage-gated sodium/potassium channels, which induces abnormal, depressed cardiovascular profiles.

Cocaine exerts its action in a several types of adverse health effects, including acute toxic effects (i.e. overdose, accidental injury and violence), dependence, cardiovascular disease and mental disorders. Epidemiological evidence suggests that cocaine use increases the risk of hemorrhagic and ischemic strokes. The toxic effects of various forms of cocaine (cocaine hydrochloride and cocaine base, i.e. crack) depend on the mode of administration (oral, nasal, intravenous, inhaled) and intake amount. The short-term effects of cocaine can be felt almost immediately after a single dose of the drug, and may last for 15 or 30 minutes to an hour. In small amounts, cocaine can quickly enters the bloodstream and creates an intense rush or euphoric effect and make someone feel energetic, talkative and mentally alert. Prolonged use may result in itching, hallucinations and paranoid delusions. Abnormal high body temperature and elevation of blood pressure, which can be life threatening and death, could result from overdosed intake.

SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC

CAS Nr: 50-36-2

References:

  1. Verlander JM Jr, Johns ME. The clinical use of cocaine. Otolaryngol Clin North Am. 1981; 14(3):521‐531.
  2. Kim ST, Park T. Acute and Chronic Effects of Cocaine on Cardiovascular Health. Int J Mol Sci. 2019; 20(3):584.
  3. Washton AM, Tatarsky A. Adverse effects of cocaine abuse. NIDA Res Monogr. 1984; 49:247‐254.
  4. Sordo L, Indave BI, Barrio G, Degenhardt L, de la Fuente L, Bravo MJ. Cocaine use and risk of stroke: A systematic review. Drug and Alcohol Dependence. 2014; 142: 1-13.

Figures:

  1. https://de.wikipedia.org/wiki/Cocastrauch
  2. https://www.alamy.com/stock-photo/cocaine-powder.html
  3. JChem for office (Excel) and Marvin/JChem 17.21.0, 2019 ChemAxon (https:www.chemaxon.com)