Chemistry:Eseroline

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Short description: Opioid analgesic compound
Eseroline
Skeletal formula
Ball-and-stick model
Clinical data
Other namesEseroline
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  (verify)

Eseroline is a drug which acts as an opioid agonist.[1] It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible,[2][3] and it produces fairly potent analgesic effects mediated through the μ-opioid receptor.[4] This mixture of activities gives eseroline an unusual pharmacological profile,[5][6] although its uses are limited by side effects such as respiratory depression[7] and neurotoxicity.[8]

References

  1. "Direct evidence that eseroline possesses morphine-like effects". European Journal of Pharmacology 83 (3–4): 233–41. September 1982. doi:10.1016/0014-2999(82)90256-4. PMID 6293841. 
  2. "Opiatelike actions of eseroline, an eserine derivative". Canadian Journal of Physiology and Pharmacology 59 (3): 307–10. March 1981. doi:10.1139/y81-048. PMID 7194726. 
  3. "Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine". Biochemical Pharmacology 31 (7): 1233–8. April 1982. doi:10.1016/0006-2952(82)90009-0. PMID 7092918. 
  4. "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 18 (3): 461–7. November 1980. PMID 7464812. 
  5. "Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences". The Journal of Pharmacy and Pharmacology 48 (11): 1164–8. November 1996. doi:10.1111/j.2042-7158.1996.tb03914.x. PMID 8961166. 
  6. "Effect of eseroline on schedule-controlled behavior in the rat". Pharmacology, Biochemistry, and Behavior 38 (4): 747–51. April 1991. doi:10.1016/0091-3057(91)90236-U. PMID 1871191. 
  7. "Effects of eseroline on the ventilatory response to CO2". European Journal of Pharmacology 232 (1): 21–8. February 1993. doi:10.1016/0014-2999(93)90723-U. PMID 8458393. 
  8. "Eseroline, a metabolite of physostigmine, induces neuronal cell death". Toxicology and Applied Pharmacology 106 (1): 28–37. October 1990. doi:10.1016/0041-008X(90)90102-Z. PMID 2251681. https://zenodo.org/record/1258264.