Noribogaminalog

{{Chembox  | ImageFile = Noribogaminalog.svg | ImageClass = skin-invert-image | ImageSize = | ImageAlt =  | IUPACName = 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indole | OtherNames = ''N''-Desmethylibogaminalog  | Section1 = {{Chembox Identifiers | CASNo = 7546-78-3 | ChEMBL = 310620 | ChemSpiderID = 25647 | EC_number = 982-798-9 | InChI = 1S/C12H14N2/c1-2-4-11-9(3-1)10-5-7-13-8-6-12(10)14-11/h1-4,13-14H,5-8H2 | InChIKey = NGUNYFTXLWTSNC-UHFFFAOYSA-N | PubChem = 27557 | SMILES = C1CNCCC2=C1C3=CC=CC=C3N2 }} | Section2 = {{Chembox Properties | C=12 | H=14 | N=2 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Noribogaminalog''', or '''''N''-desmethylibogaminalog''', also known as '''1,2,3,4,5,6-hexahydroazepino[4,5-b]indole''', is a chemical compound and parent structure of the ibogalog group of compounds.<ref name="TaeOrtellsTekarli2023" /><ref name="SuttonWilliamsHomsi2022" /><ref name="CameronTombariLu2021" /> The ibogalogs that have been described include ibogaminalog, ibogainalog, noribogainalog, tabernanthalog, catharanthalog, fluorogainalog, LS-22925, PNU-22394, and PHA-57378, among others.<ref name="TaeOrtellsTekarli2023">{{cite journal | vauthors = Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR | 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 Chem Neurosci | volume = 14 | issue = 14 | pages = 2537–2547 | date = July 2023 | pmid = 37386821 | doi = 10.1021/acschemneuro.3c00212 | url = }}</ref><ref name="SuttonWilliamsHomsi2022">{{cite journal | vauthors = Sutton C, Williams EQ, Homsi H, Beerepoot P, Nazari R, Han D, Ramsey AJ, Mash DC, Olson DE, Blough B, Salahpour A | title = Structure-Activity Relationships of Dopamine Transporter Pharmacological Chaperones | journal = Front Cell Neurosci | volume = 16 | issue = | article-number = 832536 | date = 2022 | pmid = 35614973 | pmc = 9124866 | doi = 10.3389/fncel.2022.832536 | doi-access = free | url = }}</ref><ref name="CameronTombariLu2021">{{cite journal | vauthors = Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE | title = A non-hallucinogenic psychedelic analogue with therapeutic potential | journal = Nature | volume = 589 | issue = 7842 | pages = 474–479 | date = January 2021 | pmid = 33299186 | pmc = 7874389 | doi = 10.1038/s41586-020-3008-z | bibcode = 2021Natur.589..474C | url = }}</ref><ref name="JensenPlathPedersen2013">{{cite journal | vauthors = Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, Stensbøl TB, Gloriam DE, Krogsgaard-Larsen P, Frølund B | title = Design, synthesis, and pharmacological characterization of N- and O-substituted 5,6,7,8-tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol analogues: novel 5-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties | journal = J Med Chem | volume = 56 | issue = 3 | pages = 1211–1127 | date = February 2013 | pmid = 23301527 | doi = 10.1021/jm301656h | url = }}</ref><ref name="EnnisHoffmanGhazal2003">{{cite journal | vauthors = Ennis MD, Hoffman RL, Ghazal NB, Olson RM, Knauer CS, Chio CL, Hyslop DK, Campbell JE, Fitzgerald LW, Nichols NF, Svensson KA, McCall RB, Haber CL, Kagey ML, Dinh DM | title = 2,3,4,5-tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[1,7-a]indoles: new templates for 5-HT(2C) agonists | journal = Bioorg Med Chem Lett | volume = 13 | issue = 14 | pages = 2369–2372 | date = July 2003 | pmid = 12824036 | doi = 10.1016/s0960-894x(03)00403-7 | url = }}</ref> The ibogalogs, specifically ibogainalog and analogues, were first described in the scientific literature by 1968.<ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = The iboga alkaloids are long overdue for a detailed examination of their psychic effects in man. It is interesting that simplification of the iboga structure to give the hexahydroazepino[4,5-b]indoles (for example, 4.42) enhances the tryptamine-like properties, at least as far as tremorogenic activity is concerned, but also enhances the sedative effects. Thus, these compounds have chlorpromazine-like properties in both man and animals (Hester, Tang, Keesling, and Veldkamp, 1968).}}</ref><ref name="HesterTangKeasling1968">{{cite journal | vauthors = Hester JB, Tang AH, Keasling HH, Veldkamp W | title = Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles | journal = J Med Chem | volume = 11 | issue = 1 | pages = 101–106 | date = January 1968 | pmid = 5637151 | doi = 10.1021/jm00307a023 | url = }}</ref>

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/861 Noribogaminalog - Isomer Design] * [https://www.neuwritewest.org/blog/ibogalogs-drug-discovery-and-the-new-psychedelic-era Ibogalogs, Drug Discovery, and the New Psychedelic Era - NeuWrite West]

Category:Ibogalogs