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Eseroline

Opioid analgesic compound

Eseroline

Opioid analgesic compound

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Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor. This mixture of activities gives eseroline an unusual pharmacological profile, although its uses are limited by side effects such as respiratory depression and neurotoxicity.

Synthesis

The alkylation of phenacetin (1) with dimethyl sulfate gives N-methylphenetidine (2). Treatment with 2-bromopropanoyl bromide gives 2-bromo-N-(4-ethoxyphenyl)-N-methylpropanamide (3). Treatment with aluminium trichloride results in 1,3-dimethyl-5-hydroxyoxindole (4). Alkylation with diethyl sulfate gives 5-ethoxy-1,3-dimethylindolin-2-one (5). Base-catalyzed treatment with chloroacetonitrile gives 2-(5-ethoxy-1,3-dimethyl-2-oxoindol-3-yl)acetonitrile (6). Catalytic hydrogenation of the nitrile group gives (7). Mono-methylation of the primary amine gives (8). Intramolecular reductive amination gives eserethole (9). Cleavage of the ethyl ether protecting group gave (-)-eseroline (10). Optional treatment with methyl isocyanide (MIC) leads to physostigmine.

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References

References

  1. (September 1982). "Direct evidence that eseroline possesses morphine-like effects". European Journal of Pharmacology.
  2. (March 1981). "Opiatelike actions of eseroline, an eserine derivative". Canadian Journal of Physiology and Pharmacology.
  3. (April 1982). "Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine". Biochemical Pharmacology.
  4. (November 1980). "Structure--activity relationships of eseroline and morphine: ab initio quantum-chemical study of the electrostatic potential and of the interaction energy with water". Molecular Pharmacology.
  5. (November 1996). "Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences". The Journal of Pharmacy and Pharmacology.
  6. (April 1991). "Effect of eseroline on schedule-controlled behavior in the rat". Pharmacology, Biochemistry, and Behavior.
  7. (February 1993). "Effects of eseroline on the ventilatory response to CO2". European Journal of Pharmacology.
  8. (October 1990). "Eseroline, a metabolite of physostigmine, induces neuronal cell death". Toxicology and Applied Pharmacology.
  9. (2009). "A novel and efficient total synthesis of (±)-physostigmine". Tetrahedron Letters.
  10. (1954). "Hydroxytryptamines. Part II. A new synthesis of physostigmine.". Journal of the Chemical Society (Resumed).
  11. (January 1978). "New total synthesis of dl-physostigmine (dl-eserine) via regioselective NaBH4-reduction of imides.". Tetrahedron.
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semisynthetic-opioids pyrroloindoles hydroxyarenes mu-opioid-receptor-agonists human-drug-metabolites
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