Ibogaminalog

{{Short description|Chemical compound}}

{{infobox drug

| synonyms = DM-506

| image = Ibogaminalog.svg

| image_class = skin-invert-image

| width = 200px

| legal_UK =

| legal_DE =

| C = 13 | H = 16 | N = 2

| IUPAC_name = 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole

| CAS_number = 7546-66-9

| CAS_number_Ref = {{cascite|correct|CAS}}

| ChEMBL =

| ChemSpiderID = 22605

| PubChem = 24183

| UNII =

| smiles = CN1CCC2=C(CC1)NC3=CC=CC=C23

| StdInChI = 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

| StdInChIKey = WBCPONKOWIDTJM-UHFFFAOYSA-N

}}

Ibogaminalog (developmental code name DM-506) is a drug first invented in the 1960s,{{cite patent | country = US | number = 3529062 | url = https://patents.google.com/patent/US3529062A | inventor = Renner U | assign = Novartis Corp. | gdate = 15 September 1970 | title = Indole derivatives as antitussive agents. }} 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 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.{{cite journal | vauthors = Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR | title = Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the GABA_A receptor and Ca_V2.2 channel | journal = Biochemical Pharmacology | volume = 223 | pages = 116183 | date = May 2024 | pmid = 38580167 | doi = 10.1016/j.bcp.2024.116183 | pmc = 11151864 }}{{cite journal | vauthors = 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 | display-authors = 6 | title = Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT_2A receptor activation | journal = Biomedicine & Pharmacotherapy | volume = 177 | pages = 116867 | date = June 2024 | pmid = 38889634 | doi = 10.1016/j.biopha.2024.116867 | url = https://hal.science/hal-04618390 | hdl = 2158/1371514 | hdl-access = free }}{{cite journal | vauthors = 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 | display-authors = 6 | title = 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-HT_2A receptor activation | journal = European Journal of Pharmacology | volume = 966 | pages = 176329 | date = March 2024 | pmid = 38253116 | doi = 10.1016/j.ejphar.2024.176329 | hdl = 2158/1354752 | hdl-access = free }}{{cite journal | vauthors = Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, Smith C, Manetti D, Romanelli MN, Arias HR, Gipson CD, Mitra S | display-authors = 6 | title = Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex | journal = Neurochemistry International | volume = 178 | pages = 105785 | date = June 2024 | pmid = 38838988 | doi = 10.1016/j.neuint.2024.105785 | hdl = 2158/1371513 | hdl-access = free }}{{cite journal | vauthors = Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR | display-authors = 6 | title = 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 | journal = ACS Chemical Neuroscience | volume = 14 | issue = 14 | pages = 2537–2547 | date = July 2023 | pmid = 37386821 | doi = 10.1021/acschemneuro.3c00212 }}