eseroline

{{Short description|Opioid analgesic compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| verifiedrevid = 445987820

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

| image = Eseroline_skeletal.svg

| alt = Skeletal formula

| width = 200

| image2 = Eseroline molecule ball.png

| alt2 = Ball-and-stick model

| tradename =

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| legal_UK =

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| routes_of_administration =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 469-22-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Q22H41O18D

| ATC_prefix = none

| ATC_suffix =

| PubChem = 119198

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID = 106485

| ChEBI = 48845

| StdInChI = 1S/C13H18N2O/c1-13-6-7-14(2)12(13)15(3)11-5-4-9(16)8-10(11)13/h4-5,8,12,16H,6-7H2,1-3H3/t12-,13+/m1/s1

| StdInChIKey = HKGWQUVGHPDEBZ-OLZOCXBDSA-N

| C=13 | H=18 | N=2 | O=1

| smiles = C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)O)C)C

| synonyms = Eseroline

}}

Eseroline is a drug which acts as an opioid agonist.{{cite journal | vauthors = Fürst S, Friedmann T, Bartolini A, Bartolini R, Aiello-Malmberg P, Galli A, Somogyi GT, Knoll J | title = Direct evidence that eseroline possesses morphine-like effects | journal = European Journal of Pharmacology | volume = 83 | issue = 3–4 | pages = 233–41 | date = September 1982 | pmid = 6293841 | doi = 10.1016/0014-2999(82)90256-4 }} It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible,{{cite journal | vauthors = Jhamandas K, Elliott J, Sutak M | title = Opiatelike actions of eseroline, an eserine derivative | journal = Canadian Journal of Physiology and Pharmacology | volume = 59 | issue = 3 | pages = 307–10 | date = March 1981 | pmid = 7194726 | doi = 10.1139/y81-048 }}{{cite journal | vauthors = Galli A, Renzi G, Grazzini E, Bartolini R, Aiello-Malmberg P, Bartolini A | title = Reversible inhibition of acetylcholinesterase by eseroline, an opioid agonist structurally related to physostigmine (eserine) and morphine | journal = Biochemical Pharmacology | volume = 31 | issue = 7 | pages = 1233–8 | date = April 1982 | pmid = 7092918 | doi = 10.1016/0006-2952(82)90009-0 }} and it produces fairly potent analgesic effects mediated through the μ-opioid receptor.{{cite journal | vauthors = Agresti A, Buffoni F, Kaufman JJ, Petrongolo C | title = Structure--activity relationships of eseroline and morphine: ab initio quantum-chemical study of the electrostatic potential and of the interaction energy with water | journal = Molecular Pharmacology | volume = 18 | issue = 3 | pages = 461–7 | date = November 1980 | pmid = 7464812 }} This mixture of activities gives eseroline an unusual pharmacological profile,{{cite journal | vauthors = Galli A, Ranaudo E, Giannini L, Costagli C | title = Reversible inhibition of cholinesterases by opioids: possible pharmacological consequences | journal = The Journal of Pharmacy and Pharmacology | volume = 48 | issue = 11 | pages = 1164–8 | date = November 1996 | pmid = 8961166 | doi = 10.1111/j.2042-7158.1996.tb03914.x | s2cid = 45395195 | doi-access = free }}{{cite journal | vauthors = Liu WF | title = Effect of eseroline on schedule-controlled behavior in the rat | journal = Pharmacology, Biochemistry, and Behavior | volume = 38 | issue = 4 | pages = 747–51 | date = April 1991 | pmid = 1871191 | doi = 10.1016/0091-3057(91)90236-U | s2cid = 12857298 }} although its uses are limited by side effects such as respiratory depression{{cite journal | vauthors = Berkenbosch A, Rupreht J, DeGoede J, Olievier CN, Wolsink JG | title = Effects of eseroline on the ventilatory response to CO2 | journal = European Journal of Pharmacology | volume = 232 | issue = 1 | pages = 21–8 | date = February 1993 | pmid = 8458393 | doi = 10.1016/0014-2999(93)90723-U }} and neurotoxicity.{{cite journal | vauthors = Somani SM, Kutty RK, Krishna G | title = Eseroline, a metabolite of physostigmine, induces neuronal cell death | journal = Toxicology and Applied Pharmacology | volume = 106 | issue = 1 | pages = 28–37 | date = October 1990 | pmid = 2251681 | doi = 10.1016/0041-008X(90)90102-Z | bibcode = 1990ToxAP.106...28S | url = https://zenodo.org/record/1258264 }}