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'''DM-506''' ('''Ibogaminalog''') is a drug first invented in the 1960s,<ref>[https://patents.google.com/patent/US3529062A Renner U. Indole derivatives as antitussive agents. US3529062]</ref> which acts as both a [[partial agonist]] at the [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]], and a [[negative allosteric modulator]] at the α7 and α9α10 [[nicotinic acetylcholine receptor]]s. 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]].<ref>Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR. 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. ''Biochem Pharmacol''. 2024 May;223:116183. {{doi|10.1016/j.bcp.2024.116183}} {{pmid|38580167}}</ref><ref>Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, Marin P, Ponimaskin E, Manetti D, Romanelli MN, Ghelardini C, Liechti ME, Di Cesare Mannelli L. Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT2A receptor activation. ''Biomed Pharmacother''. 2024 Jun 17;177:116867. {{doi|10.1016/j.biopha.2024.116867}} {{pmid|38889634}}</ref><ref>Arias HR, Rudin D, Hines DJ, Contreras A, Gulsevin A, Manetti D, Anouar Y, De Deurwaerdere P, Meiler J, Romanelli MN, Liechti ME, Chagraoui A. 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. ''Eur J Pharmacol''. 2024 Mar 5;966:176329. {{doi|10.1016/j.ejphar.2024.176329}} {{pmid|38253116}}</ref><ref>Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, Smith C, Manetti D, Romanelli MN, Arias HR, Gipson CD, Mitra S. Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex. ''Neurochem Int''. 2024 Jun 3;178:105785. {{doi|10.1016/j.neuint.2024.105785}} {{pmid|38838988}}</ref><ref>Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR. 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 Chem Neurosci''. 2023 Jul 19;14(14):2537-2547. {{doi|10.1021/acschemneuro.3c00212}} {{pmid|37386821}}</ref>
'''DM-506''' ('''Ibogaminalog''') is a drug first invented in the 1960s,<ref>https://patents.google.com/patent/US3529062A Renner U. Indole derivatives as antitussive agents. </ref> which acts as both a [[partial agonist]] at the [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]], and a [[negative allosteric modulator]] at the α7 and α9α10 [[nicotinic acetylcholine receptor]]s. 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]].<ref>Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the receptor and .2 channel 223116183 |10.1016/j.bcp.2024.116183 }}</ref><ref>Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, Marin P, Ponimaskin E, Manetti D, Romanelli MN, Ghelardini C, Liechti ME, Di Cesare Mannelli L Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5- receptor activation 177116867 |10.1016/j.biopha.2024.116867 }}</ref><ref>Arias HR, Rudin D, Hines DJ, Contreras A, Gulsevin A, Manetti D, Anouar Y, De Deurwaerdere P, Meiler J, Romanelli MN, Liechti ME, Chagraoui A 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- receptor activation 966176329 |10.1016/j.ejphar.2024.176329 }}</ref><ref>Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, Smith C, Manetti D, Romanelli MN, Arias HR, Gipson CD, Mitra S Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex 178105785 |10.1016/j.neuint.2024.105785 }}</ref><ref>Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR 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 1414 |10.1021/acschemneuro.3c00212 }}</ref>


== See also ==
== See also ==

Revision as of 04:32, 8 July 2024

DM-506
Identifiers
  • 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H16N
Molar mass186.278 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

References

  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. 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 = Biomedecine & Pharmacotherapie. 177: 116867. doi:10.1016/j.biopha.2024.116867. 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. 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. 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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