Eseroline
Grundinformationen
- CAS
469-22-7- Standard-SMILES
CN1CC[C@@]2(C)c3cc(O)ccc3N(C)[C@@H]12- InChIKey
HKGWQUVGHPDEBZ-OLZOCXBDSA-N- Summenformel
- C13H18N2O
- Durchschnittliche Molmasse
- 218,29 g/mol
- Monoisotopische Masse
- 218,1419132
Überblick
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.
Namen und Bezeichner
- Bevorzugter Name
- Eseroline
- IUPAC
- (3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-ol
- Englischer Name
- Eseroline
- Summenformel
- C13H18N2O
- Molmasse
- 218.29
Namen und Synonyme
Eseroline469-22-7(-)-Eseroline(3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-olDTXSID30891448Q22H41O18DCHEBI:48845MCV 4481(3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-olNIH 10398Pyrrolo(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
Weitere Namen anzeigen
(3aS)-1,2,3,3a,8,8a-Hexahydro-1,3aα,8α-trimethylpyrrolo[2,3-b]indol-5-ol(-)-Eseroline DISCONTINUED. Offer only E889163
Pyrrolo[2,3-b]indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, (3aS,8aR)-RefChem:137866DTXCID801030561(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-olCHEMBL310934eseroline-(-)ESEROLINE, (-)-SCHEMBL150460
Datenbank-Bezeichner
- CAS
469-22-7- PubChem CID
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,8
- Polarare Oberfläche (TPSA)
- 26,7 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 296
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
149.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
141.83 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 128 °C · 128 °C
- Siedepunkt
- 366.3 · 366.3±42.0 °C(Predicted)
- Dichte
- 1.16 · 1.160±0.06 g/cm3(Predicted)
- pka
- 10.17 · 10.17±0.40(Predicted)
- 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
- InChIKey
- HKGWQUVGHPDEBZ-OLZOCXBDSA-N
- SMILES
- N1(C)C2=C(C=C(O)C=C2)[C@]2(C)CCN(C)[C@]12[H]
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological ClassificationCompounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS.
Anwendungen
BeschreibungEseroline 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.
OccurrenceEseroline, although derived from physostigmine by hydrolysis of N-methylcarbamoil group, is also structurally related to morphine.
Verwenden(-)-Eseroline is a metabolite of physostigmine, displaying both anti-acetylcholinesterase and opiate agonist activities.
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