{{Short description|Class of chemical compounds}} [[File:Tabernanthalog.svg|thumb|right|250px|class=skin-invert-image|Chemical structure of tabernanthalog (TBG; DLX-007), one of the most well-known ibogalogs.<ref name="CameronTombariLu2021" />]]
An '''ibogalog''', or '''simplified ibogaine analogue''', also known as a '''substituted 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole''' (or simply '''substituted hexahydroazepinoindole'''), is a derivative of noribogaminalog and a simplified analogue of iboga alkaloids and related compounds such as ibogaine.<ref name="CameronTombariLu2021" /><ref name="AriasRudinLuethi2025" /><ref name="IyerFavelaZhang2021">{{cite journal | vauthors = Iyer RN, Favela D, Zhang G, Olson DE | title = The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs | journal = Nat Prod Rep | volume = 38 | issue = 2 | pages = 307–329 | date = March 2021 | pmid = 32794540 | pmc = 7882011 | doi = 10.1039/d0np00033g | url = }}</ref><ref name="ZiębaStępnickiMatosiuk2021">{{cite journal | vauthors = Zięba A, Stępnicki P, Matosiuk D, Kaczor AA | title = Overcoming Depression with 5-HT<sub>2A</sub> Receptor Ligands | journal = International Journal of Molecular Sciences | volume = 23 | issue = 1 | date = December 2021 | page = 10 | pmid = 35008436 | pmc = 8744644 | doi = 10.3390/ijms23010010 | doi-access = free }}</ref> They are tricyclic cyclized tryptamines and are closely related to the β-carbolines or harmala alkaloids.<ref name="CameronTombariLu2021" /><ref name="AriasRudinLuethi2025" /><ref name="ZiębaStępnickiMatosiuk2021" /> However, ibogalogs have a mostly-hydrogenated 7-membered azepine ring instead of the variably-saturated 6-membered pyridine ring present in β-carbolines.<ref name="CameronTombariLu2021" /><ref name="AriasRudinLuethi2025" /> Relative to the iboga alkaloids, ibogalogs retain the indole and hydrogenated azepine rings, but the isoquinuclidine (2-azabicyclo[2.2.2]octane) ring system has been removed, simplifying the chemical structure.<ref name="CameronTombariLu2021" /><ref name="ZiębaStępnickiMatosiuk2021" />
==Use and effects== Ibogalogs have been limitedly tested in humans, but anecdotal reports concerning tabernanthalog exist.<ref name="Love2024">{{cite web | last=Love | first=Shayla | title=Tripping on Nothing | website=The Atlantic | date=20 October 2024 | url=https://www.theatlantic.com/health/archive/2024/10/psychedelic-trip-high-hallucination-medicine/680314/ | archive-url=https://archive.today/20250208021014/https://www.theatlantic.com/health/archive/2024/10/psychedelic-trip-high-hallucination-medicine/680314/ | archive-date = 8 February 2025}}</ref><ref name="Hardman2023">{{cite web | last=Hardman | first=Josh | title=Non-Hallucinogenic Trip Reports: Searching for the Tabernanthalog Tasters | website=Psychedelic Alpha | date=19 July 2023 | url=https://psychedelicalpha.com/news/non-hallucinogenic-trip-reports-searching-for-the-tabernanthalog-tasters | access-date=14 October 2025}}</ref><ref name="Juliani2023">{{cite web | last=Juliani | first=Arthur | title=A Phenomenological Report on the Novel Non-Hallucinogenic Psychedelic Tabernanthalog | website=Medium | date=30 December 2023 | url=https://archive.today/20251014085657/https://awjuliani.medium.com/a-phenomenological-report-on-the-novel-non-hallucinogenic-psychedelic-tabernanthalog-ed2fc601c1dc | access-date=14 October 2025}}</ref>
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== Ibogalogs are known to act as potent serotonin 5-HT<sub>2A</sub> and 5-HT<sub>2C</sub> receptor agonists, as well as acting as agonists of other serotonin receptors.<ref name="AriasRudinLuethi2025">{{cite journal | vauthors = Arias HR, Rudin D, Luethi D, Valenta J, Leśniak A, Czartoryska Z, Olejarz-Maciej A, Doroz-Płonka A, Manetti D, De Deurwaerdère P, Romanelli MN, Handzlik J, Liechti ME, Chagraoui A | title = The psychoplastogens ibogaminalog and ibogainalog induce antidepressant-like activity in naïve and depressed mice by mechanisms involving 5-HT2A receptor activation and serotonergic transmission | journal = Prog Neuropsychopharmacol Biol Psychiatry | volume = 136 | issue = | article-number = 111217 | date = January 2025 | pmid = 39662723 | doi = 10.1016/j.pnpbp.2024.111217 | url = | doi-access = free }}</ref><ref name="ZiębaStępnickiMatosiuk2021" /><ref name="FitzgeraldEnnis2002">{{cite book | last1=Fitzgerald | first1=Lawrence W | last2=Ennis | first2=Michael D | title=Annual Reports in Medicinal Chemistry | chapter=Chapter 3: 5-HT2C receptor modulators: Progress in development of new CNS medicines | publisher=Elsevier | volume=37 | date=2002 | isbn=978-0-12-040537-4 | doi=10.1016/s0065-7743(02)37004-0 | pages=21–30 | quote=The closely related azepinoindole 11 (PNU-22394) has been described as a 5-HT2C agonist (Ki = 18.8 nM, 83% efficacy) that has recently been reported to decrease feeding in rats and produce a weight loss in humans (68). Although dose-related clinical side effects observed included headache, anxiety, nausea, and vomiting, these effects were dramatically reduced following four days of dosing. No hallucinations were observed despite the fact that 11 is also a potent, high efficacy 5-HT2A agonist (5-HT2A Ki = 19 nM, 64% efficacy). Compound 11 also has excellent affinity at 5-HT2B receptors (Ki = 28.5 nM).}}</ref> This is in contrast to iboga alkaloids like ibogaine and noribogaine, which are inactive as serotonin receptor agonists.<ref name="CameronTombariLu2021" /> Ibogalogs also possess other actions, such as serotonin 5-HT<sub>2B</sub> receptor antagonism or partial agonism,<ref name="AriasRudinLuethi2025" /> monoamine reuptake inhibition,<ref name="AriasRudinLuethi2025" /> and nicotinic acetylcholine receptor inhibition.<ref name="TaeOrtellsTekarli2023">{{cite journal | last1=Tae | first1=Han-Shen | last2=Ortells | first2=Marcelo O. | last3=Tekarli | first3=Bassel J. | last4=Manetti | first4=Dina | last5=Romanelli | first5=Maria Novella | last6=McIntosh | first6=J. Michael | last7=Adams | first7=David J. | last8=Arias | first8=Hugo R. | title=DM506 (3-Methyl-1,2,3,4,5,6-hexahydroazepino[4,5- b ]indole fumarate), a Novel Derivative of Ibogamine, Inhibits α7 and α9α10 Nicotinic Acetylcholine Receptors by Different Allosteric Mechanisms | journal=ACS Chemical Neuroscience | volume=14 | issue=14 | date=19 July 2023 | issn=1948-7193 | doi=10.1021/acschemneuro.3c00212 | pages=2537–2547 | pmid=37386821 | url=https://pubs.acs.org/doi/10.1021/acschemneuro.3c00212 | access-date=28 July 2025| url-access=subscription }}</ref><ref name="TaeOrtellsYousuf2024">{{cite journal | vauthors = Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR | title = Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the GABAA receptor and CaV2.2 channel | journal = Biochem Pharmacol | volume = 223 | issue = | article-number = 116183 | date = May 2024 | pmid = 38580167 | pmc = 11151864 | doi = 10.1016/j.bcp.2024.116183 | url = }}</ref> Unlike iboga alkaloids like noribogaine, they show no opioid receptor agonism, for instance of the κ-opioid receptor.<ref name="CameronTombariLu2021" /> In addition, the compounds have dramatically reduced potency at the hERG antitarget compared to ibogaine, which confers much less cardiotoxicity.<ref name="CameronTombariLu2021" /><ref name="ZiębaStępnickiMatosiuk2021" />
Ibogalogs have been reported to produce psychoplastogenic,<ref name="AriasRudinLuethi2025" /><ref name="CameronTombariLu2021">{{cite journal | vauthors = Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C | url = }}</ref> antidepressant-like,<ref name="AriasRudinLuethi2025" /><ref name="CameronTombariLu2021" /> anxiolytic-like,<ref name="AriasRudinHines2024">{{cite journal | last1=Arias | first1=Hugo R. | last2=Rudin | first2=Deborah | last3=Hines | first3=Dustin J. | last4=Contreras | first4=April | last5=Gulsevin | first5=Alican | last6=Manetti | first6=Dina | last7=Anouar | first7=Youssef | last8=De Deurwaerdere | first8=Philippe | last9=Meiler | first9=Jens | last10=Romanelli | first10=Maria Novella | last11=Liechti | first11=Matthias E. | last12=Chagraoui | first12=Abdeslam | title=The novel non-hallucinogenic compound DM506 (3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole) induces sedative- and anxiolytic-like activity in mice by a mechanism involving 5-HT2A receptor activation | journal=European Journal of Pharmacology | volume=966 | date=2024 | doi=10.1016/j.ejphar.2024.176329 | doi-access=free | article-number=176329 | pmid=38253116 | url=https://flore.unifi.it/bitstream/2158/1354752/1/Anxiolytic%20and%20sedative%20activity%20of%20DM506%20PRINT.pdf | access-date=28 July 2025}}</ref> sedative-like,<ref name="AriasRudinHines2024" /><ref name="BrimblecombePinder1975" /> antiaddictive-like,<ref name="CameronTombariLu2021" /><ref name="HeinsbroekGiannottiBonilla2023">{{cite journal | vauthors = Heinsbroek JA, Giannotti G, Bonilla J, Olson DE, Peters J | title = Tabernanthalog Reduces Motivation for Heroin and Alcohol in a Polydrug Use Model | journal = Psychedelic Med (New Rochelle) | volume = 1 | issue = 2 | pages = 111–119 | date = June 2023 | pmid = 37360328 | pmc = 10286262 | doi = 10.1089/psymed.2023.0009 | url = }}</ref> and analgesic effects in animals.<ref name="AriasMicheliRudin2024">{{cite journal | vauthors = Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, Marin P, Ponimaskin E, Manetti D, Romanelli MN, Ghelardini C, Liechti ME, Di Cesare Mannelli L | title = Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT2A receptor activation | journal = Biomed Pharmacother | volume = 177 | issue = | article-number = 116867 | date = August 2024 | pmid = 38889634 | doi = 10.1016/j.biopha.2024.116867 | url = | hdl = 2158/1371514 | hdl-access = free }}</ref><ref name="AriasMicheliJensen2025">{{cite journal | vauthors = Arias HR, Micheli L, Jensen AA, Galant S, Vandermoere F, Venturi D, Manetti D, Romanelli MN, Ghelardini C, Marin P, Di Cesare Mannelli L | title = Ibogalogs decrease neuropathic pain in mice through a mechanism involving crosstalk between 5-HT2A and mGlu2 receptors | journal = Biomed Pharmacother | volume = 184 | issue = | article-number = 117887 | date = March 2025 | pmid = 39938347| doi = 10.1016/j.biopha.2025.117887 | url = | hdl = 2158/1423286 | hdl-access = free }}</ref> Based on the rodent head-twitch response, a behavioral proxy of serotonergic psychedelic activity, ibogainalog may produce psychedelic effects in humans, while other assessed ibogainalogs, including tabernanthalog, ibogaminalog, noribogainalog, and catharanthalog, appear to be non-psychedelic.<ref name="CameronTombariLu2021" /><ref name="AriasRudinHines2024" /><ref name="AriasMicheliJensen2025" /><ref name="ZiębaStępnickiMatosiuk2021" /> In addition, PNU-22394 was non-hallucinogenic in clinical studies.<ref name="FitzgeraldEnnis2002" />
==History== Ibogalogs, such as PNU-22394, were first developed and described in the 1960s.<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = The iboga alkaloids are long overdue for a detailed examination of their psychic effects in man. It is interesting that simplification of the iboga structure to give the hexahydroazepino[4,5-b]indoles (for example, 4.42) enhances the tryptamine-like properties, at least as far as tremorogenic activity is concerned, but also enhances the sedative effects. Thus, these compounds have chlorpromazine-like properties in both man and animals (Hester, Tang, Keesling, and Veldkamp, 1968).}}</ref><ref name="HesterTangKeasling1968">{{cite journal | vauthors = Hester JB, Tang AH, Keasling HH, Veldkamp W | title = Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles | journal = J Med Chem | volume = 11 | issue = 1 | pages = 101–106 | date = January 1968 | pmid = 5637151 | doi = 10.1021/jm00307a023 | url = }}</ref> In the early 2000s, ibogalogs like PNU-22394 were studied and described further as potential appetite suppressants and weight loss drugs.<ref name="McCallFranklinHyslop2001" /><ref name="FitzgeraldEnnis2002" /><ref name="BishopNilsson2003" /> Subsequently, ibogalogs were studied and described in the early 2020s and thereafter, including by David E. Olson and colleagues at the University of California, Davis and Delix Therapeutics, as potential treatments of central nervous system disorders.<ref name="ChemistryWorld2020">{{cite web | last1=Extance | first1=Andy | last2=Extance | first2=Andy | last3=McVean | first3=Ada | last4=Robinson | first4=Julia | last5=Welter | first5=Kira | last6=Durrani | first6=Jamie | last7=Extance | first7=Andy | title=Chemists tame shamanic addiction treatment | website=Chemistry World | date=17 December 2020 | url=https://www.chemistryworld.com/news/chemists-tame-shamanic-addiction-treatment/4012926.article | access-date=28 July 2025}}</ref><ref name="CameronTombariLu2021" /><ref name="AriasRudinLuethi2025" /> Relatedly, tabernanthalog (TBG; DLX-007) is under development for potential medical use.<ref name="CameronTombariLu2021" /><ref>{{cite web | title=DLX 7 | website=AdisInsight | date=20 February 2023 | url=https://adisinsight.springer.com/drugs/800063581 | access-date=18 November 2024}}</ref><ref>{{cite web | title=Delving into the Latest Updates on DLX-7 with Synapse | website=Synapse | date=7 November 2024 | url=https://synapse.patsnap.com/drug/27dc3166d63441e88619c8b30cb536e4 | access-date=18 November 2024}}</ref>
==List of ibogalogs== {{Sticky}} {| class="wikitable sticky-header" |- ! Structure !! Name !! Synonyms !! Chemical name !! Iboga analogue !! Ref |- | class=skin-invert-image|115px || Noribogaminalog || || 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole || Noribogamine || <ref name="HesterTangKeasling1968" /> |- | class=skin-invert-image|115px || Ibogaminalog || DM-506 || 3-methyl-2,4,5,6-tetrahydro-1''H''-azepino[4,5-b]indole || Ibogamine || |- | class=skin-invert-image|115px || Noribogainalog || Nor-IBG; GATC-021 || 9-hydroxy-3-methyl-2,4,5,6-tetrahydro-1''H''-azepino[4,5-b]indole || Noribogaine || <ref name="LallaiKhoMartin2026" /> |- | class=skin-invert-image|115px || Ibogainalog || IBG || 9-methoxy-3-methyl-2,4,5,6-tetrahydro-1''H''-azepino[4,5-b]indole || Ibogaine || <ref name="CameronTombariLu2021" /> |- | class=skin-invert-image|115px || GATC-1021 || 8-Fluoroibogainalog || 8-fluoro-9-methoxy-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole || || <ref name="LallaiKhoMartin2026">{{cite journal | vauthors = Lallai V, Kho S, Martin AC, Fowler JP, Roach ML, Wang K, Laumann KN, Morrison TG, Palaniappan M, Bautista M, Mogul AS, Cheepluesak JE, Shrestha B, Lade DM, Lagomarsino JE, Narayan V, Uffens J, Lernhardt W, Mirzaei S, Jenkins I, Zavala AR, Lakey JR, Tinder R, Fowler CD | title = AI-derived therapeutic development of a serotonin receptor-targeting drug for the treatment of opioid use disorder | journal = Proc Natl Acad Sci U S A | volume = 123 | issue = 15 | article-number = e2516807123 | date = April 2026 | pmid = 41941629 | doi = 10.1073/pnas.2516807123 | url = }}</ref> |- | class=skin-invert-image|115px || Tabernanthalog || TBG; DLX-007 || 8-methoxy-3-methyl-2,4,5,6-tetrahydro-1''H''-azepino[4,5-b]indole || Tabernanthine || <ref name="CameronTombariLu2021" /> |- | class=skin-invert-image|115px || Catharanthalog || CAG || methyl 3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate || Catharanthine || <ref>{{cite web | title=Methyl 3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/20642897 | access-date=28 July 2025}}</ref><ref name="AriasMicheliJensen2025" /> |- | class=skin-invert-image|115px || Pharm-136 || || 7-methyl-10-hydroxy-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole || || <ref name="Sabnis2025">{{cite journal | vauthors = Sabnis RW | title = Novel Azepinoindoles as 5‑HT2C Agonists for Treating Depression, Drug Addiction, Alcoholism, PTSD, and Neuropathic Pain | journal = ACS Med Chem Lett | volume = 16 | issue = 8 | pages = 1507–1508 | date = August 2025 | pmid = 40832530 | doi = 10.1021/acsmedchemlett.5c00426 | url = }}</ref><ref name="WO2023212811">{{cite web | title=Azepinoindoles and methods of preparation thereof | website=Google Patents | date=2 May 2023 | url=https://patents.google.com/patent/WO2023212811A1/en | access-date=3 April 2026}}</ref> |- | class=skin-invert-image|115px || Fluorogainalog || || 9-fluoro-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole || || <ref>{{cite web | title=9-fluoro-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/154694310 | access-date=28 July 2025}}</ref><ref name="SuttonWilliamsHomsi2022">{{cite journal | vauthors = Sutton C, Williams EQ, Homsi H, Beerepoot P, Nazari R, Han D, Ramsey AJ, Mash DC, Olson DE, Blough B, Salahpour A | title = Structure-Activity Relationships of Dopamine Transporter Pharmacological Chaperones | journal = Front Cell Neurosci | volume = 16 | issue = | article-number = 832536 | date = 2022 | pmid = 35614973 | pmc = 9124866 | doi = 10.3389/fncel.2022.832536 | doi-access = free | url = }}</ref> |- | class=skin-invert-image|115px || LS-22925 || || 9-fluoro-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole || || <ref>{{cite web | title=9-Fluoro-1,2,3,4,5,6-hexahydro-azepino(4,5-b)indole | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/substance/49872882 | access-date=28 July 2025}}</ref> |- | class=skin-invert-image|115px || PNU-22394 || U-22394 || 6-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole || || <ref name="McCallFranklinHyslop2001">McCall, R. B., Franklin, S. R., Hyslop, D. K., Knauer, C. S., Chio, C. L., Haber, C. L., & Fitzgerald, L. W. (2001). PNU-22394, a 5-HT2C receptor agonist, reduces feeding in rodents and produces weight loss in humans. In Soc Neurosci Abstr (Vol. 27, No. 309.2). https://scholar.google.com/scholar?cluster=17067737110870651783</ref><ref name="BishopNilsson2003">{{cite journal | last1=Bishop | first1=Michael J | last2=Nilsson | first2=Björn M | title=New 5-HT2C receptor agonists | journal=Expert Opinion on Therapeutic Patents | volume=13 | issue=11 | date=2003 | issn=1354-3776 | doi=10.1517/13543776.13.11.1691 | pages=1691–1705 | url=http://www.tandfonline.com/doi/full/10.1517/13543776.13.11.1691 | access-date=28 July 2025| url-access=subscription }}</ref> |- |}
==Related compounds== {{Sticky}} {| class="wikitable sticky-header" |- ! Structure !! Name !! Synonyms !! Chemical name !! Ref |- | class=skin-invert-image|125px || 4-Allyl-6-oxa-noribogainalog || || 3-methyl-4-prop-2-enyl-1,2,4,5-tetrahydro-[1]benzofuro[2,3-d]azepin-9-ol || <ref name="RennerKargbo2026">{{cite journal | last1=Renner | first1=Anna C. | last2=Kargbo | first2=Robert B. | title=Advances in Psychedelic Therapeutics: Multimodal Iboga Analogs, EEG-Guided Psilocybin Dosing, and Optimized Harmine–DMT Formulations | journal=ACS Medicinal Chemistry Letters | volume=17 | issue=1 | date=8 January 2026 | issn=1948-5875 | pmid=41531985 | pmc=12794085 | doi=10.1021/acsmedchemlett.5c00714 | pages=72–74 | url=https://pubs.acs.org/doi/10.1021/acsmedchemlett.5c00714 | access-date=13 April 2026}}</ref><ref name="WO2025166273">{{cite web | title=Novel analogs of oxa-iboga class of therapeutics | website=Google Patents | date=31 January 2025 | url=https://patents.google.com/patent/WO2025166273A1/en | access-date=13 April 2026}}</ref> |- | class=skin-invert-image|115px || PHA-57378 || || 2,7,8,9,10,11-hexahydro-1''H''-azepino[4,5-b][1,4]oxazino[2,3,4-hi]indole || |- | class=skin-invert-image|115px || PNU-181731 || || 2,3,4,5-tetrahydro-1''H''-[1,4]diazepino[1,7-a]indole || |}
==See also== * Azepinoindole * Iboga alkaloid * 5-MeO-IsoqT * Oxa-noribogaine * Substituted β-carboline * Substituted 3-benzazepine * Substituted tetrahydroisoquinoline * Non-hallucinogenic 5-HT<sub>2A</sub> receptor agonist
==References== {{Reflist}}
{{Tryptamines}} {{Chemical classes of psychoactive drugs}}
Category:Chemical classes of psychoactive drugs Category:Ibogalogs