Eseroline

Eseroline
Skeletal formula
Ball-and-stick model
Clinical data
ATC code none
Identifiers
Synonyms Eseroline
CAS Number 469-22-7 YesY
PubChem (CID) 119198
ChemSpider 106485
ChEBI CHEBI:48845
Chemical and physical data
Formula C13H18N2O
Molar mass 218.295 g/mol
3D model (Jmol) Interactive image
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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. ↑ Fürst, S; Friedmann, T; Bartolini, A; Bartolini, R; Aiello-Malmberg, P; Galli, A; Somogyi, GT; Knoll, J (1982). "Direct evidence that eseroline possesses morphine-like effects". European Journal of Pharmacology. 83 (3–4): 233–41. doi:10.1016/0014-2999(82)90256-4. PMID 6293841.
  2. ↑ Jhamandas, K; Elliott, J; Sutak, M (1981). "Opiatelike actions of eseroline, an eserine derivative". Canadian Journal of Physiology and Pharmacology. 59 (3): 307–10. PMID 7194726.
  3. ↑ Galli, A; Renzi, G; Grazzini, E; Bartolini, R; Aiello-Malmberg, P; Bartolini, A (1982). "Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine". Biochemical pharmacology. 31 (7): 1233–8. doi:10.1016/0006-2952(82)90009-0. PMID 7092918.
  4. ↑ Agresti, A; Buffoni, F; Kaufman, JJ; Petrongolo, C (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. 18 (3): 461–7. PMID 7464812.
  5. ↑ Galli, A; Ranaudo, E; Giannini, L; Costagli, C (1996). "Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences". The Journal of pharmacy and pharmacology. 48 (11): 1164–8. doi:10.1111/j.2042-7158.1996.tb03914.x. PMID 8961166.
  6. ↑ Liu, WF (1991). "Effect of eseroline on schedule-controlled behavior in the rat". Pharmacology, Biochemistry, and Behavior. 38 (4): 747–51. doi:10.1016/0091-3057(91)90236-U. PMID 1871191.
  7. ↑ Berkenbosch, A; Rupreht, J; Degoede, J; Olievier, CN; Wolsink, JG (1993). "Effects of eseroline on the ventilatory response to CO2". European Journal of Pharmacology. 232 (1): 21–8. doi:10.1016/0014-2999(93)90723-U. PMID 8458393.
  8. ↑ Somani, SM; Kutty, RK; Krishna, G (1990). "Eseroline, a metabolite of physostigmine, induces neuronal cell death". Toxicology and applied pharmacology. 106 (1): 28–37. doi:10.1016/0041-008X(90)90102-Z. PMID 2251681.


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