17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene hydrochloride

• ChemBase ID: 131210
• Molecular Formular: C20H27ClN2O
• Molecular Mass: 346.89418
• Monoisotopic Mass: 346.18119117
• SMILES: CCC1CC2CC3C1N(C2)CCc1c3[nH]c2c1cc(cc2)OC.Cl
• Canonical SMILES: CCC1CC2CN3C1C(C2)c1[nH]c2c(c1CC3)cc(cc2)OC.Cl
• InChI: InChI=1S/C20H26N2O.ClH/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19;/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3;1H
• InChIKey: IKJFDJLQPHDRTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4(9),5,7-tetraene hydrochloride
• IUPAC Traditional name: 17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.0^2,^1^0.0^4,^9.0^1^3,^1^8]nonadeca-2(10),4(9),5,7-tetraene hydrochloride
• Synonyms: Ibogaine hydrochloride

Database IDs

• CAS Number: 5934-55-4
• EC Number: 227-687-1
• MDL Number: MFCD00167426
• PubChem SID: 162225488
• PubChem CID: 363271

CALCULATED PROPERTIES

• Acid pKa: 17.082462
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.34782717
• LogD (pH = 7.4): 1.9568198
• Log P: 3.5312593
• Molar Refractivity: 93.5725 cm^3
• Polarizability: 37.535976 Å^3
• Polar Surface Area: 28.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble; methanol: soluble

Safety Information

• RTECS: NH6730000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 22-26-37/39-45
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

DETAILS

Sigma Aldrich - I7003

Preparation Note
Alkaloid isolated from the African shrub, Tabernanthe iboga.
Biochem/physiol Actions
Ibogaine is a central nervous system stimulant and hallucinogen that has been reported to be a σ2 agonist, a noncompetitive NMDA receptor antagonist at the phencyclidine site and an enhancer of purinergic muscle contractions. It is also a competitive inhibitor of serotonin and dopamine transport. It is an anti-convulsant and has anti-addictive properties against cocaine and heroin.