25I-NBOMe

25i-nbome (also known as 2c-i-nbome, cimbi-5 and n-bomb) is a novel psychedelic substance of the phenethylamine chemical class that produces an array of visually-dominant and stimulating psychedelic effects when administered.

the name 25i-nbome, which short-hand for 2c-i-nbome, is a derivative of the phenethylamine psychedelic 2c-i. it was first synthesized and documented in 2003 by ralf heim at the free university of berlin. it was further researched 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 nbome 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-nbome in humans. it had no history of human use before being sold online as a designer drug in 2010.. it has been associated with many deaths and hospitalizations. anecdotal reports suggest that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.

chemistry

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.

pharmacology

25i-nbome has efficacy at the 5-ht_2a receptor where it acts as an unusually potent and selective partial agonist. 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. contrary to popular belief, it is not a “full agonist”, 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.