Compound: Eseroline
SMILES: Oc1cc2c(N(C)[C@@H]3[C@]2(CCN3C)C)cc1
InChIKey: HKGWQUVGHPDEBZ-OLZOCXBDSA-N
Synonyms: Eseroline, 469-22-7, (-)-Eseroline, (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol, DTXSID30891448, Q22H41O18D, CHEBI:48845, MCV 4481, (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol, NIH 10398, Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-, (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo(2,3-b)indol-5-ol, Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-, RefChem:137866, DTXCID801030561, (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol, CHEMBL310934, eseroline-(-), ESEROLINE, (-)-, SCHEMBL150460, UNII-Q22H41O18D, SCHEMBL30142606, BDBM93695, cid_45479742, PYRROLO(2,3-B)INDOL-5-OL, 1,2,3,3A,8,8A-HEXAHYDRO-1,3A,8-TRIMETHYL-, (3AS-CIS)-, BDBM50292538, AKOS024282669, NCGC00017362-02, NCGC00142536-01, AC-37403, FE162095, ST057526, Q5397651, BRD-K13629382-051-06-6, (3aS,8aR)-1,8,3a-trimethylpyrrolidino[2,3-b]indolin-5-ol, (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrol[2,3-b]indol-7-ol;maleate, (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol;(Z)-2-butenedioate, (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol;(Z)-but-2-enedioate, (3AS,8AR)-1,2,3,3A,8,8A-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)INDOL-5-OL, Eseroline  (-)-Eseroline  (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-ol
Theoretical properties:
molecular_formula: C13H18N2O
molecular_weight: 218.29 g/mol
exact_mass: 218.141913202 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 0
heavy_atom_count: 16
topological_polar_surface_area: 26.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Eseroline is a pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP. It has a role as an opioid analgesic and a human xenobiotic metabolite. It is a member of phenols and a pyrroloindole.
chebi: A pyrroloindole that is 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-<em>b</em>]indole substituted by methyl groups at positions 1, 3a and 8 and a hydroxy group at position 5. It is a metabolite of physostigmine and causes neuronal cell death by a mechanism involving loss of cell ATP.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Eseroline is a drug which acts as an opioid agonist. It is a metabolite of the acetylcholinesterase inhibitor physostigmine but unlike physostigmine, the acetylcholinesterase inhibition produced by eseroline is weak and easily reversible, and it produces fairly potent analgesic effects mediated through the μ-opioid receptor. This mixture of activities gives eseroline an unusual pharmacological profile, although its uses are limited by side effects such as respiratory depression and neurotoxicity.