| Class: | Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Psychoplastogen |
| Cas Number: | 802581-10-8 |
| Pubchem: | 370423 |
| Chemspiderid: | 328813 |
| Chembl: | 2009371 |
| Synonyms: | IBG; 9-Methoxyibogaminalog; 9-MeO-ibogaminalog |
| Iupac Name: | 9-methoxy-3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole |
| C: | 14 |
| H: | 18 |
| N: | 2 |
| O: | 1 |
| Smiles: | CN1CCC2=C(CC1)NC3=C2C=C(C=C3)OC |
| Stdinchi: | 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 |
| Stdinchikey: | 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). Unlike noribogaine, IBG shows no activation of the opioid receptors or κ-opioid receptor agonism. In addition to its actions at serotonin receptors, IBG inhibits certain nicotinic acetylcholine receptors.[4]
The drug produces the head-twitch response in animals and hence shows psychedelic-like effects. However, it has reduced hallucinogen-like effects compared to 5-MeO-DMT. Conversely, tabernanthalog (TBG), a simplified analogue of tabernanthine and positional isomer of IBG, appears to be completely non-hallucinogenic. IBG shows comparable psychoplastogenic activity to ibogaine. In contrast to ibogaine, IBG and TBG appear to have much less or no potential for cardiotoxicity secondary to hERG inhibition. However, TBG showed a better overall safety profile than IBG and was selected for development instead of IBG. IBG shows analgesic effects against neuropathic pain and visceral pain in animals that appear to be mediated by serotonin 5-HT2A receptor activation.[5]
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. Owing to their simplified structures, the chemical syntheses of IBG and TBG are much more practical than the synthesis of ibogaine.