Eseroline

Eseroline

Systematic (IUPAC) name
(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol
Clinical data
Legal status	?
Identifiers
CAS number	469-22-7 Y
ATC code	None
PubChem	CID 119198
ChemSpider	106485
Synonyms	Eseroline
Chemical data
Formula	C13H18N2O
Mol. mass	218.295 g/mol
SMILES C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)O)C)C
InChI InChI=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 Key:HKGWQUVGHPDEBZ-OLZOCXBDSA-N
Y (what is this?)  (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. ↑ 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.