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Ibogainalog

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Ibogainalog
Clinical data
Other namesIBG; 9-Methoxyibogaminalog; 9-MeO-ibogaminalog
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Psychoplastogen
Identifiers
  • 9-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC14H18N2O
Molar mass230.311 g·mol−1
3D model (JSmol)
  • CN1CCC2=C(CC1)NC3=C2C=C(C=C3)OC
  • InChI=1S/C14H18N2O/c1-16-7-5-11-12-9-10(17-2)3-4-13(12)15-14(11)6-8-16/h3-4,9,15H,5-8H2,1-2H3
  • Key:RVVJOBLZASPMDJ-UHFFFAOYSA-N

Ibogainalog (IBG), also known as 9-methoxyibogaminalog, is a serotonergic psychedelic and psychoplastogen related to ibogaine but with a simplified chemical structure.[1][2][3]

It acts as a serotonin 5-HT2A receptor agonist, serotonin 5-HT2B receptor antagonist, and also interacts with other serotonin receptors, such as the serotonin 5-HT1F receptor (agonist), 5-HT2C receptor (very weak partial agonist or antagonist), and 5-HT6 receptor (agonist).[3][4] Unlike noribogaine, IBG shows no activation of the opioid receptors or κ-opioid receptor agonism.[3] In addition to its actions at serotonin receptors, IBG inhibits certain nicotinic acetylcholine receptors.[5]

The drug produces the head-twitch response in animals and hence shows psychedelic-like effects.[1][3] However, it has reduced hallucinogen-like effects compared to 5-MeO-DMT.[1] Conversely, tabernanthalog (TBG), a simplified analogue of tabernanthine and positional isomer of IBG, appears to be completely non-hallucinogenic.[1][3] IBG shows comparable psychoplastogenic activity to ibogaine.[1] In contrast to ibogaine, IBG and TBG appear to have much less or no potential for cardiotoxicity secondary to hERG inhibition.[1][3] However, TBG showed a better overall safety profile than IBG and was selected for development instead of IBG.[1][3] IBG shows analgesic effects against neuropathic pain and visceral pain in animals that appear to be mediated by serotonin 5-HT2A receptor activation.[4]

IBG can be viewed as a conformationally restricted analogue of 5-MeO-DMT, whereas TBG can be viewed as a conformationally restricted analogue of 6-MeO-DMT.[2][3] Owing to their simplified structures, the chemical syntheses of IBG and TBG are much more practical than the synthesis of ibogaine.[1]

See also

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References

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  1. ^ a b c d e f g h Zięba A, Stępnicki P, Matosiuk D, Kaczor AA (December 2021). "Overcoming Depression with 5-HT2A Receptor Ligands". Int J Mol Sci. 23 (1). doi:10.3390/ijms23010010. PMC 8744644. PMID 35008436.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  2. ^ a b Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.
  3. ^ a b c d e f g h 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 (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. doi:10.1038/s41586-020-3008-z. PMC 7874389. PMID 33299186.
  4. ^ a b 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 (August 2024). "Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT2A receptor activation". Biomed Pharmacother. 177: 116867. doi:10.1016/j.biopha.2024.116867. PMID 38889634.
  5. ^ Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR (May 2024). "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". Biochem Pharmacol. 223: 116183. doi:10.1016/j.bcp.2024.116183. PMID 38580167.
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