25I-NBOH
25I-NBOH is a synthetic psychedelic of the substituted phenethylamine class, specifically an N-benzylated derivative of 2C-I. First synthesized in 2006 by a team led by David Nichols at Purdue University, it is a close structural analog of 25I-NBOMe and is reported to share most of its properties, though with moderately reduced potency and a shorter duration. It is a known metabolite of 25I-NBOMe and has also been encountered as a designer drug.1
Contents
Dosage & Duration
Dosage
Heavy doses may be fatal. Absorption requires 15-25 minutes of sublingual contact. Expect strong metallic taste and numbness of the mouth lasting up to an hour.
Duration
Subjective Effects
25I-NBOH produces a stimulating psychedelic experience active at sub-milligram sublingual or buccal doses, typically in the range of 300 to 1,000 μg. The experience combines prominent open- and closed-eye visuals with euphoria, enhanced empathy, and a general alteration of perception, alongside a noticeable stimulant character. A softening of the sense of self and moments of insight are reported, though confusion can also occur. The stimulating quality frequently makes sleep difficult until the effects have fully subsided.
Physical
The body load is distinctly stimulating, with restlessness, muscle tension, appetite suppression, and pupil dilation. Alternating sweating and chills reflect disrupted temperature regulation, and insomnia commonly persists through the tail of the experience.
Stimulation
The experience carries a pronounced stimulant component affecting both mind and body.
Uncomfortable
Cognitive
The headspace is euphoric and emotionally open, with enhanced empathy and a capacity for personal insight. The sense of self can soften, and confusion may arise, particularly at higher intensities.
Emotional
Visual
Visual effects include color brightening and hallucinatory activity visible with eyes both open and closed.
Tactile
Tactile sensation is enhanced.
Reagent Testing
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Pharmacology
Pharmacodynamics
25I-NBOH acts as a potent agonist at the serotonin 5-HT2A receptor, with a Ki of 0.061 nM and an EC50 of 0.074 nM at the human receptor. It has been identified as one of the most selective 5-HT2A agonist ligands known, with one study reporting more than 400-fold selectivity over the 5-HT2C receptor, though another study found only approximately 6-fold selectivity for 5-HT2A over 5-HT2C.2 The compound produces the head-twitch response in rodents, a behavioral indicator consistent with psychedelic-like activity.3
Pharmacokinetics
Dangerous
Highest riskThese combinations are considered extremely harmful and should always be avoided. Reactions to these drugs taken in combination are highly unpredictable and have a potential to cause death.
Unsafe
AvoidThere is considerable risk of physical harm when taking these combinations, they should be avoided where possible.
Caution
Use cautionThese combinations are not usually physically harmful, but may produce undesirable effects, such as physical discomfort or overstimulation. Extreme use may cause physical health issues. Synergistic effects may be unpredictable. Care should be taken when choosing to use this combination.
Tolerance
Serotonergic psychedelics
Harm Potential
Addiction & Dependence
Psychological
Extremely Low25I-NBOH is not habit-forming, and repeated use may reduce the desire to take it. Its use is usually self-regulating.
Psychosis Risk
Anxiety and paranoia appear to occur more readily with 25I-NBOH than with typical psychedelics, possibly due to its stimulating properties. At high doses, overwhelming cognitive alterations including confusion and sensory overload may occur.
Seizure Risk
Seizures are listed among possible physical effects. Risk may be elevated in susceptible individuals.4
History & Culture
25I-NBOH was first synthesized in 2006 by a research team at Purdue University working under the direction of David Nichols. The compound was developed as part of ongoing investigations into serotonin receptor pharmacology, with particular interest in its potential application as a radioligand for…
Trip Reports
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Legality
By Country
References
Source Pages
Citations
- Poklis JL, Dempsey SK, Liu K, Ritter JK, Wolf C, Zhang S, & Poklis A. (2015). Identification of Metabolite Biomarkers of the Designer Hallucinogen 25I-NBOMe in Mouse Hepatic Microsomal Preparations and Human Urine Samples Associated with Clinical Intoxication. Journal of Analytical Toxicology, 39(8). https://pmc.ncbi.nlm.nih.gov/articles/PMC4570938/1
- (December 2018). Neurochemical pharmacology of psychoactive substituted N-benzylphenethylamines: High potency agonists at 5-HT2A receptors. Biochemical Pharmacology, 158, 27–34. https://doi.org/10.1016/j.bcp.2018.09.0241
- (May 2020). Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species. Neuropharmacology, 167. https://doi.org/10.1016/j.neuropharm.2019.1079331
- Zawilska JB, Kacela M, & Adamowicz P. (2020). NBOMes–Highly Potent and Toxic Alternatives of LSD. Frontiers in Neuroscience, 14, 78. https://doi.org/10.3389/fnins.2020.000781
- (April 2011). Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers. European Journal of Nuclear Medicine and Molecular Imaging, 38(4), 681–693. https://doi.org/10.1007/s00259-010-1686-81
- (2017). Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens. Current Topics in Behavioral Neurosciences, 32, 283–311. https://doi.org/10.1007/7854_2016_641
- (2017). Preventing misidentification of 25I-NBOH as 2C-I on routine GC–MS analyses. Forensic Toxicology, 35(2), 415–420. https://doi.org/10.1007/s11419-017-0362-01
- (2016-11-21). Neue-psychoaktive-Stoffe-Gesetz (NpSG). Bundesministerium der Justiz (Federal Ministry of Justice, Germany). https://www.gesetze-im-internet.de/npsg/BJNR261510016.html12
- (2015-08-18). Nio nya ämnen narkotikaklassas — Läkemedelsverket (Medical Products Agency Sweden, HSLF-FS 2015:12). Läkemedelsverket (Swedish Medical Products Agency). https://www.mynewsdesk.com/se/lakemedelsverket/pressreleases/nio-nya-aemnen-narkotikaklassas-12013841
- (1971). Misuse of Drugs Act 1971, Schedule 2 (as amended by S.I. 2014/1106). UK Parliament / legislation.gov.uk. https://www.legislation.gov.uk/ukpga/1971/38/schedule/21
Further Reading
Åstrand et al. 2020 - Off-target μ-opioid receptor activity of 25I-NBOH and analogues- Coelho Neto et al. 2017 - 25I-NBOH: a new potent serotonin 5-HT2A receptor agonist identified in blotter paper seizures in Brazil
EMCDDA: Europol 25I-NBOH Early-warning brief, 2016
Ettrup et al. 25I-NBOH: a high-affinity 5-HT2A agonist for PET imaging. Journal of Medicinal Chemistry 2011;54(13): 4802-4815.
Automated synthesisInformation aggregated and synthesized using an autonomous workflow built by Josie Kins.
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