DM-506: Difference between revisions

DM-506
Identifiers
	IUPAC name 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole;
CAS Number	7546-66-9 ;
PubChem CID	24183;
CompTox Dashboard (EPA)	DTXSID70226391 ;
Chemical and physical data
Formula	C13H16N
Molar mass	186.278 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC2=C(CC1)NC3=CC=CC=C23;
	InChI 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;

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Revision as of 22:47, 6 July 2024

DM-506 (Ibogaminalog) is a drug first developed in the 1960s,^[1] which acts as both a partial agonist at the 5-HT_2A receptor, and a negative allosteric modulator at the α7 and α9α10 nicotinic acetylcholine receptors. It was derived by structural simplification of ibogaine and has been researched both for anti-addictive effects and for the treatment of neuropathic pain.^[2]^[3]^[4]^[5]^[6]

References

^ Renner U. Indole derivatives as antitussive agents. US3529062
^ 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
^ 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
^ 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
^ 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
^ 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

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[1] Renner U. Indole derivatives as antitussive agents. US3529062

[2] 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

[3] 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

[4] 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

[5] 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

[6] 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

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-'''DM-506''' ('''Ibogaminalog''') is a drug 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 was derived by structural simplification 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 developed 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 was derived by structural simplification 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>
 == See also ==