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DM-506

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DM-506
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

DM-506 (ibogaminalog) is a drug first invented in the 1960s,[1] which acts as both a partial agonist at the 5-HT2A receptor, and a negative allosteric modulator at the α7 and α9α10 nicotinic acetylcholine receptors. It can be regarded as a structurally simplified derivative of ibogaine and has been researched both for anti-addictive effects and for the treatment of neuropathic pain.[2][3][4][5][6]

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. ^ 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. ^ 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. ^ 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. ^ 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.


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