Eseroline

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IUPAC_name = (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo [2,3-b] indol-7-ol


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CAS_number = 469-22-7
synonyms = Eseroline
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PubChem = 119198
smiles = C [C@@] 12CCN( [C@@H] 1N(C3=C2C=C(C=C3)O)C)C
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C = 13 | H = 18 | N = 2 | O = 1
molecular_weight = 218.295 g/mol
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Eseroline is a drug which acts as an opioid agonist. [Fürst S, Friedmann T, Bartolini A, Bartolini R, Aiello-Malmberg P, Galli A, Somogyi GT, Knoll J. Direct evidence that eseroline possesses morphine-like effects. "European Journal of Pharmacology". 1982 Sep 24;83(3-4):233-41. PMID 6293841] It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, [Jhamandas K, Elliott J, Sutak M. Opiatelike actions of eseroline, an eserine derivative. "Canadian Journal of Physiology and Pharmacology". 1981 Mar;59(3):307-10. PMID 7194726] [Galli A, Renzi G, Grazzini E, Bartolini R, Aiello-Malmberg P, Bartolini A. Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine. "Biochemical Pharmacology". 1982 Apr 1;31(7):1233-8. PMID 7092918] and it produces fairly potent analgesic effects mediated through the μ-opioid receptor. [Agresti A, Buffoni F, Kaufman JJ, Petrongolo C. 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". 1980 Nov;18(3):461-7. PMID 7464812] This mixture of activities gives eseroline an unusual pharmacological profile, [Galli A, Ranaudo E, Giannini L, Costagli C. Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences. "Journal of Pharmacy and Pharmacology". 1996 Nov;48(11):1164-8. PMID 8961166] [Liu WF. Effect of eseroline on schedule-controlled behavior in the rat. "Pharmacology, Biochemistry and Behaviour". 1991 Apr;38(4):747-51. PMID 1871191] although its uses are limited by side effects such as respiratory depression [Berkenbosch A, Rupreht J, DeGoede J, Olievier CN, Wolsink JG. Effects of eseroline on the ventilatory response to CO2. "European Journal of Pharmacology". 1993 Feb 23;232(1):21-8. PMID 8458393] and neurotoxicity. [Somani SM, Kutty RK, Krishna G. Eseroline, a metabolite of physostigmine, induces neuronal cell death. "Toxicology and Applied Pharmacology". 1990 Oct;106(1):28-37. PMID 2251681]

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