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Ibogaminalog

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Ibogaminalog
Clinical data
Other namesDM-506; DM506
Drug classNon-selective serotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor partial agonist
Identifiers
  • 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H16N2
Molar mass200.285 g·mol−1
3D model (JSmol)
  • CN1CCC2=C(CC1)NC3=CC=CC=C23
  • InChI=1S/C13H16N2/c1-15-8-6-11-10-4-2-3-5-12(10)14-13(11)7-9-15/h2-5,14H,6-9H2,1H3
  • Key:WBCPONKOWIDTJM-UHFFFAOYSA-N

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

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Ibogaminalog is known to act as an agonist of serotonin receptors, including of the serotonin 5-HT2A receptor (Ki = 17–11,190 nM; EC50Tooltip half-maximal effective concentration = 2.9–34 nM; EmaxTooltip maximal efficacy = 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 (ImaxTooltip maximal inhibition = 14%).[4][3][7][8]

It is a weak to very weak monoamine reuptake inhibitor, including of serotonin, norepinephrine, and dopamine (IC50Tooltip half-maximal inhibitory concentration = 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

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References

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  1. ^ US 3529062, Renner U, "Indole derivatives as antitussive agents.", issued 15 September 1970, assigned to Novartis Corp. 
  2. ^ a b 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". Biochemical Pharmacology. 223: 116183. doi:10.1016/j.bcp.2024.116183. PMC 11151864. PMID 38580167.
  3. ^ a b c Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, et al. (June 2024). "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: 116867. doi:10.1016/j.biopha.2024.116867. hdl:2158/1371514. PMID 38889634.
  4. ^ a b c d Arias HR, Rudin D, Hines DJ, Contreras A, Gulsevin A, Manetti D, et al. (March 2024). "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: 176329. doi:10.1016/j.ejphar.2024.176329. hdl:2158/1354752. PMID 38253116.
  5. ^ a b Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, et al. (June 2024). "Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex". Neurochemistry International. 178: 105785. doi:10.1016/j.neuint.2024.105785. hdl:2158/1371513. PMID 38838988.
  6. ^ Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, et al. (July 2023). "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. doi:10.1021/acschemneuro.3c00212. PMID 37386821.
  7. ^ a b c 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 (January 2025). "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: 111217. doi:10.1016/j.pnpbp.2024.111217. PMID 39662723.
  8. ^ Arias HR, Micheli L, Jensen AA, Galant S, Vandermoere F, Venturi D, Manetti D, Romanelli MN, Ghelardini C, Marin P, Di Cesare Mannelli L (March 2025). "Ibogalogs decrease neuropathic pain in mice through a mechanism involving crosstalk between 5-HT2A and mGlu2 receptors". Biomed Pharmacother. 184: 117887. doi:10.1016/j.biopha.2025.117887. PMID 39938347.
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