Ibogamine
Basic information
- CAS
481-87-8- Standard SMILES
CC[C@H]1C[C@@H]2C[C@H]3c4[nH]c5ccccc5c4CCN(C2)[C@@H]13- InChIKey
LRLCVRYKAFDXKU-YGOSVGOTSA-N- Molecular formula
- C19H24N2
- Average molar mass
- 280.4 g/mol
- Monoisotopic mass
- 280.19394877
Overview
Ibogamine is a monoterpenoid indole alkaloid with formula C19H24N2. It is isolated from the flowering plant genus, Tabernaemontana and exhibits anti-addictive properties. It has a role as a oneirogen, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and a plant metabolite. It is an organic heteropentacyclic compound, an indole alkaloid fundamental parent, a tertiary amino compound and a monoterpenoid indole alkaloid. It is a conjugate base of an ibogamine(1+).
Names & identifiers
- Preferred name
- Ibogamine
- IUPAC
- (1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene
- English name
- Ibogamine
- Molecular formula
- C19H24N2
- Molecular weight
- 280.41
Names & synonyms
Ibogamine481-87-8CHEBI:5853DTXSID30963997RefChem:923251DTXCID501391718(1R,15S,17S,18S)-17-ethyl-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4,6,8-tetraeneCHEMBL5184088(1R,15R,17S,18S)-17-Ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene(-)-ibogamineNSC 267705SCHEMBL433382
Show more names
SCHEMBL433383BDBM50597222C09215Q5984343
Database identifiers
- CAS
481-87-8- PubChem CID
- 100217
- ChEMBL
CHEMBL467828、CHEMBL5184088- ChEBI
CHEBI:5853- Nikkaji
- J12.393E
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 19 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 408
Physicochemical properties
- Melting point
- 162 · 162-164 °C
- Boiling point
- 452.2 · 452.2±35.0 °C(Predicted)
- Density
- 1.18 · 1.18±0.1 g/cm3(Predicted)
- pka
- 17.55 · 17.55±0.40(Predicted)
Chemistry & industry
Applications
UsesIbogamine is used for treatment of movement-related disorders using noribogaine.
Additional notes
DefinitionChEBI: Ibogamine is a monoterpenoid indole alkaloid with formula C19H24N2. It is isolated from the flowering plant genus, Tabernaemontana and exhibits anti-addictive properties. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a plant metabolite and a oneirogen. It is an indole alkaloid fundamental parent, an organic heteropentacyclic compound, a monoterpenoid indole alkaloid and a tertiary amino compound. It is a conjugate base of an ibogamine(1+).
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