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25I-NBOH

25I-NBOH molecule structure25I-NBOH molecule structure
2C-I-NBOH
Cimbi-27, NBOH-2C-I
Psychoactive Class
PsychedelicHallucinogen

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

Dosage & Duration

Dosage

Doses are population estimates that vary widely between individuals.

Threshold~50 µg
Light50-500 µg
Moderate500-800 µg
Strong800-1300 µg
Heavy1300+ µg

Heavy doses carry a risk of fatal overdose. A pronounced metallic taste and oral numbness are commonly reported and may persist for up to one hour.

Duration

Onset15-60 minutes
Come Up30-90 minutes
Peak2-3.5 hours
Offset1.5-2.5 hours
After Effects3-12 days
Total5-8 hours

Subjective Effects

Legacy content. A statistically backed ontology from Mindstate Design Labs is coming soon.

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.

Pupil dilation

Stimulation

The experience carries a pronounced stimulant component affecting both mind and body.

Restlessness

Uncomfortable

Muscle tensionAppetite suppression

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.

Confusion

Emotional

Visual

Visual effects include color brightening and hallucinatory activity visible with eyes both open and closed.

Tactile

Tactile sensation is enhanced.

See also: Psychedelic Intensity Scale, Effects of psychedelics (visual, cognitive, miscellaneous)

Reagent Testing

Expected colorimetric results for common reagent tests. Colors show reaction change over 1–2 minutes.

Marquis(MQ)
white → brown2
Mecke(ME)
white → brown2 → brown3
Mandelin(MD)
yellow2 → brown2
Liebermann(LB)
white → black3
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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.citation needed The compound produces the head-twitch response in rodents, a behavioral indicator consistent with psychedelic-like activity.2

Pharmacokinetics

There have been no studies on the pharmacokinetic profile of 25I-NBOH and the metabolism of 25I-NBOH is unknown.

Metabolitesnone documented yet

Interactions

Dangerous

Highest risk

These 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.

AMTLithiumPregabalin

Unsafe

Avoid

There is considerable risk of physical harm when taking these combinations, they should be avoided where possible.

AmphetaminesCocaineDXMTramadol

Caution

Use caution

These 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.

2C-T-x compounds2C-x compounds5-MeO-xxT tryptaminesCaffeineCannabisDiphenhydramineDOx compoundsMAOIsMDMAMescalineMXE
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Tolerance

Tolerance timelines are rules of thumb, not exact schedules, and vary widely between individuals and use patterns.

Full Tolerance
Tolerance to the effects of 25I-NBOH develops almost immediately after ingestion.
Baseline Reset
Approximately 2 weeks to return to baseline tolerance with no additional use.
Half Tolerance
Approximately 1 week for tolerance to reduce to half in the absence of further consumption.
Cross Tolerance

Serotonergic psychedelics

Harm Potential

Addiction & Dependence

Psychological

Extremely Low

25I-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.citation needed

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

Illegal2
Sweden flagSwedenSchedule I
United Kingdom flagUnited KingdomClass A
Controlled / restricted2
Germany flagGermanyNpSG (Controlled)
Switzerland flagSwitzerlandRestricted

References

Source Pages

  1. Erowid Experience Vaults: 25I-NBOH Reports
  2. Erowid: 25i Nboh.shtml
  3. Isomer Design (TiHKAL/PiHKAL)
  4. PsychonautWiki
  5. TripSit Factsheets
  6. TripSit: Drug Database – 25I-NBOH Fact Sheet (2024 revision)
  7. Wikipedia

Citations

  1. 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
  2. Adam L. Halberstadt, Muhammad Chatha, Adam K. Klein, Jason Wallach, & Simon D. Brandt. (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
  3. Neue-psychoaktive-Stoffe-Gesetz (NpSG). Bundesministerium der Justiz (Federal Ministry of Justice, Germany) (2016-11-21). https://www.gesetze-im-internet.de/npsg/BJNR261510016.html12
  4. Nio nya ämnen narkotikaklassas — Läkemedelsverket (Medical Products Agency Sweden, HSLF-FS 2015:12). Läkemedelsverket (Swedish Medical Products Agency) (2015-08-18). https://www.mynewsdesk.com/se/lakemedelsverket/pressreleases/nio-nya-aemnen-narkotikaklassas-12013841
  5. Rohmaterialen und Erzeugnisse mit vermuteter betäubungsmittelähnlicher Wirkung (Swissmedic). swissmedic.ch (n.d.). https://www.swissmedic.ch/dam/swissmedic/it/dokumente/bewilligungen/btm/verzeichnis_der_rohmaterialienunderzeugnissemitvermuteterbetaeub.pdf.download.pdf/indice_des_matierespremieresetproduitsayantuneffetpresumesemblab.pdf1
  6. Misuse of Drugs Act 1971, Schedule 2 (as amended by S.I. 2014/1106). UK Parliament / legislation.gov.uk (1971). https://www.legislation.gov.uk/ukpga/1971/38/schedule/21

Further Reading

  1. Åstrand et al. 2020 - Off-target μ-opioid receptor activity of 25I-NBOH and analogues
  2. Coelho Neto et al. 2017 - 25I-NBOH: a new potent serotonin 5-HT2A receptor agonist identified in blotter paper seizures in Brazil
  3. EMCDDA: Europol 25I-NBOH Early-warning brief, 2016
  4. Ettrup et al. 25I-NBOH: a high-affinity 5-HT2A agonist for PET imaging. Journal of Medicinal Chemistry 2011;54(13): 4802-4815.

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Recent changes8 human edits · latest

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