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25I-NBOH (also known as 2C-I-NBOH, NBOH-2CI, and Cimbi-27) is novel synthetic psychedelic substance of the phenethylamine chemical class that produces an array of visually-dominant and stimulating psychedelic effects when administered. It is a closely related analog of 25I-NBOMe and is reported to share most of its properties with the exception of a moderately reduced potency and a shorter duration.
The name 25I-NBOH, which short-hand for 2C-I-NBOH, is a derivative of the phenethylamine psychedelic 2C-I. It was first synthesized and documented in 2006 by a team at Purdue University led by David Nichols. It has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).
It is worth noting that compounds of the NBOH family are not orally active and should be administered sublingually by placing and holding it into one’s mouth and allowing it to absorb over a period of 15-25 minutes.
Extremely little is known about the pharmacological properties, metabolism, and toxicity of 25I-NBOH in humans. It has no history of human use before being sold online as a designer drug in 2011. It is closely related to members of the 25x-NBOMe series, specifically 25I-NBOMe, which has been associated with many deaths and hospitalizations. Anecdotal reports indicate that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.
25I-NBOH or 2C-I-NBOH, is a serotonergic N-benzyl derivative of the substituted phenethylamine psychedelic known as 2C-I. 25I-NBOH 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-hydroxybenzyl (BOH) group. 25I-NBOH shares this 2-hydroxybenzyl substitution with other chemicals of the NBOH family. This NBOH addition is comprised of a hydroxy ether OH- bound to a benzene ring at R2.
25I-NBOH has efficacy at the 5-HT2A receptor where it acts as a potent agonist.
This compound is pharmacologically unique when compared to other psychedelics due to the unusually high selectivity it displays for serotonin receptors. It is notable as one of the most selective agonist ligands for the 5-HT2A receptor with an EC50 value of 0.074 nM and more than 400x selectivity over the 5-HT2C receptor. It has a Ki of 0.061 nM at the human 5HT2A receptor, similar to the better-known compound 25I-NBOMe, making it some twelve times as potent of 2C-I itself.
However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
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