Talk:25H-NBOMe: Difference between revisions

25I-NBOMe or 2C-I-NBOMe is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as [[2C-I]]. 25I-NBOMe is a substituted phenethylamine with methoxy groups CH₃O- attached to carbons R₂ and R₅ as well as an iodine atom attached to carbon R₄. It differs from [[2C-I]] structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. 25I-NBOMe shares this 2-methoxybenzyl substitution with other chemicals of the NBOMe family. This NBOMe addition contains a methoxy ether CH₃O- bound to a benzene ring at R₂.

25I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT_2A receptor]] where it acts as an unusually potent and selective [[Agonist#Agonists|partial agonist]].<ref name="pmid21174090">Ettrup, A. E. A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging 38 (4): 681–693. (PubMed.gov / NCBI) | http://www.ncbi.nlm.nih.gov/pubmed/21174090</ref> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.

Among psychedelics, this compound is considered to be pharmacologically unique in terms of the high potency, affinity, and selectivity with which it binds to the 5-HT2a receptor.<ref name="pmid21174090" /> Contrary to popular belief, it is not a "full agonist"{{citation needed}}, although questions have been raised about how the effects it produces differ from other 5-HT2a partial agonists, which include the range of traditional psychedelics.

The Ki values of the following targets were greater than 500 Ki: 5-HT1A, D3, H2, 5-HT1D, α1A adrenergic, δ opioid, serotonin reuptake transporter, 5-HT5A, 5-HT1B, D2, 5-HT7, D1, 5-HT3, 5-HT1E, D5, muscarinic M1-M5, H3, and the dopamine reuptake transporter.<ref name="high specific">High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18468904</ref>

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|+Ki-values<ref>Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/21174090</ref><ref name="high specific" />