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Ibogaminalog

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Ibogaminalog
Clinical data
Other namesDM-506; DM506
Drug classNon-selectiveserotonin receptor modulator; Non-hallucinogenicserotonin5-HT2A receptorpartial agonist
Identifiers
  • 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number
PubChemCID
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 nameDM-506) is anon-selective and non-psychedelicserotonin receptor modulator of theibogalog group related to theiboga alkaloidibogamine but with a simplifiedchemical 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 anagonist ofserotonin receptors, including of theserotonin5-HT2A receptor (Ki = 17–11,190 nM;EC50Tooltip half-maximal effective concentration = 2.9–34 nM;EmaxTooltip maximal efficacy = 33–76%), the serotonin5-HT2B receptor (Ki = 16.5–63,780 nM;EC50 = 2.9–33 nM;Emax = 68–69%), and the serotonin5-HT6 receptor (EC50 = 2.9 nM;Emax = 96%), and as aninverse agonist of the serotonin5-HT7 receptor (ImaxTooltip maximal inhibition = 14%).[4][3][7][8]

It is a weak to very weakmonoamine reuptake inhibitor, including ofserotonin,norepinephrine, anddopamine (IC50Tooltip half-maximal inhibitory concentration = 3,100 nM, 9,500 nM, and 70,000 nM, respectively), whereas it is not a significantmonoamine oxidase inhibitor (MAOI) ofMAO-A orMAO-B.[7] The drug also acts weakly as anegative allosteric modulator of the α7 and α9α10nicotinic acetylcholine receptors.[2]

Ibogaminalog does not produce thehead-twitch response, a behavioral proxy ofpsychedelic effects, in rodents, and hence may be non-hallucinogenic in humans.[4] On the other hand, it has been found to producesedative,antidepressant-like,anxiolytic-like,antiaddictive-like, andanalgesic-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. ^abTae 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. ^abcArias 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. ^abcdArias 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. ^abLooschen 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. ^abcArias 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.hdl:2158/1423286.PMID 39938347.
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
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