Noribogaminalog
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| IUPAC name
1,2,3,4,5,6-Hexahydroazepino[4,5-b]indole
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| Other names
N-Desmethylibogaminalog
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| Identifiers | |
3D model (JSmol)
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| ChEMBL | |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C12H14N2 | |
| Molar mass | 186.258 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1][2][3] The ibogalogs that have been described include ibogaminalog, ibogainalog, noribogainalog, tabernanthalog, catharanthalog, fluorogainalog, LS-22925, PNU-22394, and PHA-57378, among others.[1][2][3][4][5] The ibogalogs, specifically ibogainalog and analogues, were first described in the scientific literature by 1968.[6][7]
See also
[edit]References
[edit]- ^ a b Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, Adams DJ, Arias HR (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 Chem Neurosci. 14 (14): 2537–2547. doi:10.1021/acschemneuro.3c00212. PMID 37386821.
- ^ a b Sutton C, Williams EQ, Homsi H, Beerepoot P, Nazari R, Han D, Ramsey AJ, Mash DC, Olson DE, Blough B, Salahpour A (2022). "Structure-Activity Relationships of Dopamine Transporter Pharmacological Chaperones". Front Cell Neurosci. 16: 832536. doi:10.3389/fncel.2022.832536. PMC 9124866. PMID 35614973.
- ^ a b 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 (January 2021). "A non-hallucinogenic psychedelic analogue with therapeutic potential". Nature. 589 (7842): 474–479. Bibcode:2021Natur.589..474C. doi:10.1038/s41586-020-3008-z. PMC 7874389. PMID 33299186.
- ^ Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, Stensbøl TB, Gloriam DE, Krogsgaard-Larsen P, Frølund B (February 2013). "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". J Med Chem. 56 (3): 1211–1127. doi:10.1021/jm301656h. PMID 23301527.
- ^ 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 (July 2003). "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". Bioorg Med Chem Lett. 13 (14): 2369–2372. doi:10.1016/s0960-894x(03)00403-7. PMID 12824036.
- ^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M.
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).
- ^ Hester JB, Tang AH, Keasling HH, Veldkamp W (January 1968). "Azepinoindoles. I. Hexahydroazepino[4,5-b]indoles". J Med Chem. 11 (1): 101–106. doi:10.1021/jm00307a023. PMID 5637151.
External links
[edit]- Noribogaminalog - Isomer Design
- Ibogalogs, Drug Discovery, and the New Psychedelic Era - NeuWrite West
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