Ibogaine






Names

    • EINECS 201-498-4
    • NIH 10567
    • (1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
    • HJM
    • (18R)-12-methoxyibogamine
    • 83-74-9
    • 12 Methoxyibogamine', "6,9-Methano-5H-pyrido(1',2':1,2)azepino(4,5-b)indole, ibogamine deriv.", "6,9-Methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole, ibogamine deriv.", '(1R,15R,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene
    • NSC 249764
    • HSIBGVUMFOSJPD-CFDPKNGZSA-N
    • CHEMBL1215855
    • UNII-3S814I130U
    • (-)-Ibogaine
    • Ibogamine, 12-methoxy-
    • Endabuse
    • IBOGAINE [MART.]
    • IBOGAINE [VANDF]
    • IBOGAINE (MART.)', "7-Ethyl-6,6beta,7,8,9,10,12,13-octahydro-2-methoxy-6,9-methano-5H-pyrido(1',2':1,2)azepino(5,4-b)indole", 'Tabernanthe iboga
    • 3S814I130U
    • FS-9083
    • IBOGAINE
    • (5beta)-12-methoxyibogamine
    • GTPL13148
    • Ibogaine
    • NSC-249764
    • DTXCID401324112
    • IBOGAINE [MI]
    • SCHEMBL113571
    • NS00041096
    • IBOGAINE [WHO-DD]
    • DEA No. 7260
    • 12-Methoxyibogamine
    • Ibogain
    • DTXSID20894069
    • Q409455
    • Ibogaine (8CI)
    • BDBM50308247
    • (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraene
    • (1R,15S,17S,18S)-17-ethyl-7-methoxy-3,13-diazapentacyclo(13.3.1.02,10.04,9.013,18)nonadeca-2(10),4(9),5,7-tetraene
    • HSDB 8180
    • CHEBI:5852

Attributes

  • Canonical SMILES

    CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC

  • InChI

    InChI=1S/C20H26N2O/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/t12-,13+,17+,20+/m1/s1

  • Molecule Class: Alkaloids
  • TPSA: 28.26
  • #RotBonds: 2
  • MW: 310.441
  • HBD: 1
  • HBA: 2
  • logP: 3.936600000000003
  • Chemical Formula: C20H26N2O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. alba Mexico 761051 132793, 133359, 161424 to 161427
    T. arborea Mexico, Costa Rica 681494 132793, 133359, 161424 to 161427
    T. australis Brazil - ICN-68457
    T. citrifolia Caribbean 141615 C.Sastre/J.Fournet2652
    T. coronaria Malaysia 52861 11429
    T. corymbosa Malaysia, China 1679252 GK604
    T. divaricata China, Japan, Thailand, Bangladesh, Vienna 52861 BBP0671
    T. penduliflora Cameroon, 37036/HNC, Nigeria 761088 40,411 HCN

External Databases


References

  • Antimycobacterial Activity of Alkaloids and Extracts from Tabernaemontana alba and T. arborea. Planta Med, 2022 (PMID 32392600).
  • Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe. FEMS Immunol Med Microbiol, 1998 (PMID 9626931).
  • Antiplasmodial activities of indole alkaloids from Tabernaemontana penduliflora K. Schum (Apocynaceae). Fitoterapia, 2021 (PMID 34029654).
  • Antituberculosis activity, phytochemical identification of Costus speciosus (J. Koenig) Sm., Cymbopogon citratus (DC. Ex Nees) Stapf., and Tabernaemontana coronaria (L.) Willd. and their effects on the growth kinetics and cellular integrity of Mycobacterium tuberculosis H37Rv. BMC Complement Altern Med, 2018 (PMID 29310671).
  • Biologically active ibogan and vallesamine derivatives from Tabernaemontana divaricata. Chem Biodivers, 2004 (PMID 17191876).
  • Central nervous system activity of a Tabernaemontana arborea alkaloid extract involves serotonergic and opioidergic neurotransmission in murine models. Fitoterapia, 2023 (PMID 37423501).
  • Cytotoxic indole alkaloids from Tabernaemontana divaricata. J Nat Prod, 2013 (PMID 23944995).
  • Indole alkaloids from Tabernaemontana australis (Muell. Arg) Miers that inhibit acetylcholinesterase enzyme. Bioorg Med Chem, 2005 (PMID 15911323).
  • New Iboga-Type Indole Alkaloids from Tabernaemontana divaricata. Nat Prod Bioprospect, 2019 (PMID 31724098).
  • Quantification of Anti-Addictive Alkaloids Ibogaine and Voacangine in In Vivo- and In Vitro-Grown Plants of Two Mexican Tabernaemontana Species. Chem Biodivers, 2016 (PMID 27448833).
  • Vobatensines A-F, Cytotoxic Iboga-Vobasine Bisindoles from Tabernaemontana corymbosa. J Nat Prod, 2016 (PMID 26918761).

Compound-Protein Relationships


Compound Activities

    • Inhibitory
    • Ambulatory
    • Antituberculosis
    • Anticholinesterase
    • Antidepressant
    • Antiaddictive
    • Antimycobacterial
    • Cidal
    • Antinociceptive
    • Growth inhibitory
    • Cytotoxicity

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.71
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.96
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Substrate
    Skin Permeability -1.54
    Distribution Blood-Brain Barrier (Central Nervous System) -3.18
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.51
    Plasma Protein Binding 62.84
    Steady State Volume of Distribution 2.55
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Inhibitor
    CYP 2D6 Substrate Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 9.12
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.28
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -1.02
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 7.32
    Micronucleos Toxic
    NR-AhR Toxic
    NR-AR Safe
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -1.92
    Rat (Acute) 3.03
    Rat (Chronic Oral) 1.67
    Fathead Minnow 4.08
    Respiratory Disease Toxic
    Skin Sensitisation Safe
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 408.47
    Hydration Free Energy -4.71
    Log(D) at pH=7.4 3.35
    Log(P) 3.56
    Log S -3.16
    Log(Vapor Pressure) -7.62
    Melting Point 200.39
    pKa Acid 12.85
    pKa Basic 8.61