Chemistry:Ibogaminalog

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Ibogaminalog (developmental code name DM-506) is a non-selective and non-psychedelic serotonin receptor modulator of the ibogalog group related to the iboga alkaloid ibogamine but with a simplified chemical structure. It was first described in the 1960s but was subsequently further studied and reported on in the 2020s.[1][2][3][4][5][6]

Pharmacology

Ibogaminalog is known to act as an agonist of serotonin receptors, including of the serotonin 5-HT2A receptor (Ki = 17–11,190 nM; EC50 = 2.9–34 nM; Emax = 33–76%), the serotonin 5-HT2B receptor (Ki = 16.5–63,780 nM; EC50 = 2.9–33 nM; Emax = 68–69%), and the serotonin 5-HT6 receptor (EC50 = 2.9 nM; Emax = 96%), and as an inverse agonist of the serotonin 5-HT7 receptor (Imax = 14%).[4][3][7][8]

It is a weak to very weak monoamine reuptake inhibitor, including of serotonin, norepinephrine, and dopamine (IC50 = 3,100 nM, 9,500 nM, and 70,000 nM, respectively), whereas it is not a significant monoamine oxidase inhibitor (MAOI) of MAO-A or MAO-B.[7] The drug also acts weakly as a negative allosteric modulator of the α7 and α9α10 nicotinic acetylcholine receptors.[2]

Ibogaminalog does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may be non-hallucinogenic in humans.[4] On the other hand, it has been found to produce sedative, antidepressant-like, anxiolytic-like, antiaddictive-like, and analgesic-like effects in rodents.[4][7][5][3]

See also

References

  1. ↑ Renner U, "Indole derivatives as antitussive agents.", US patent 3529062, issued 15 September 1970
  2. ↑ 2.0 2.1 "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". Biochemical Pharmacology 223. May 2024. doi:10.1016/j.bcp.2024.116183. PMID 38580167. 
  3. ↑ 3.0 3.1 3.2 "Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT2A receptor activation". Biomedicine & Pharmacotherapy 177. June 2024. doi:10.1016/j.biopha.2024.116867. PMID 38889634. https://hal.science/hal-04618390. 
  4. ↑ 4.0 4.1 4.2 4.3 "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". European Journal of Pharmacology 966. March 2024. doi:10.1016/j.ejphar.2024.176329. PMID 38253116. 
  5. ↑ 5.0 5.1 "Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex". Neurochemistry International 178. June 2024. doi:10.1016/j.neuint.2024.105785. PMID 38838988. 
  6. ↑ "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". ACS Chemical Neuroscience 14 (14): 2537–2547. July 2023. doi:10.1021/acschemneuro.3c00212. PMID 37386821. 
  7. ↑ 7.0 7.1 7.2 "The psychoplastogens ibogaminalog and ibogainalog induce antidepressant-like activity in naïve and depressed mice by mechanisms involving 5-HT2A receptor activation and serotonergic transmission". Prog Neuropsychopharmacol Biol Psychiatry 136. January 2025. doi:10.1016/j.pnpbp.2024.111217. PMID 39662723. 
  8. ↑ "Ibogalogs decrease neuropathic pain in mice through a mechanism involving crosstalk between 5-HT2A and mGlu2 receptors". Biomed Pharmacother 184. March 2025. doi:10.1016/j.biopha.2025.117887. PMID 39938347. 



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