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25C-NBOH

25C-NBOH molecule structure25C-NBOH molecule structure
2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2-hydroxyphenyl)methyl]ethanamine
2C-C-NBOH, NBOH-2C-C
Psychoactive Class

25C-NBOH is a synthetic psychedelic of the substituted phenethylamine class, produced through N-benzylation of the psychedelic 2C-C.citation needed First synthesized in 2011 by Martin Hansen at the University of Copenhagen, it has since appeared as a designer drug. It is known for producing predominantly visual and stimulating psychedelic effects, with serotonin receptor affinity comparable to its structural relative 25C-NBOMe.

Dosage & Duration

Dosage

Doses are population estimates that vary widely between individuals.

Threshold~100 μg
Light100-500 μg
Moderate500-750 μg
Strong750-1000 μg
Heavy1000+ μg

25C-NBOH and related NBOH compounds are not orally bioavailable. A bitter, metallic taste and noticeable numbing of the mouth are commonly reported, with the numbness typically lasting around an hour after the dose is absorbed. This substance has a steep dose-response relationship, and subjective effects can vary considerably even between doses of similar size.

Duration

Onset15-45 minutes
Come Up30-90 minutes
After Effects3-6 days
Total5-7 hours

Subjective Effects

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

25C-NBOH produces a stimulating psychedelic experience broadly typical of the NBOH series, combining euphoria, empathy, and a general alteration of perception with prominent visual effects visible with both open and closed eyes. The headspace tends toward insight and a softening of ego boundaries, though confusion can occur, and mental and physical stimulation often persists long enough to interfere with sleep.

Physical

The body experience is distinctly stimulating and can include restlessness, muscle tension, and alternating sweating and chills. Appetite is suppressed, pupils dilate, and insomnia is common while effects remain active.

Stimulation

Stimulation is both mental and physical, and can manifest as restlessness.

Uncomfortable

Muscle tensionAppetite suppression

Cognitive

The mental state is euphoric and empathogenic, with an insight-oriented, introspective character and a softening of the sense of self. Confusion is reported by some users, particularly as perception becomes more altered.

Confusion

Visual

Visual effects are a core feature of the experience, spanning brightened colors and visuals that appear with eyes both open and closed.

Tactile

Tactile sensation is enhanced, with touch and texture feeling more pronounced.

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 → yellow2 → orange1
Mecke(ME)
white → green2 → green3
Mandelin(MD)
yellow2 → brown2
Liebermann(LB)
white → black3
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Pharmacology

Pharmacodynamics

In vitro receptor assays found that 25C-NBOH bound human 5-HT2A receptors with pKi 9.4 and activated them with pEC50 9.43. In the same study, its affinity at rat 5-HT2C receptors was lower (pKi 7.8). These measurements characterize receptor binding and functional activity in assay systems; they do not establish human pharmacokinetics, metabolism, clinical potency, or safety.1

Pharmacokinetics

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

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
Develops almost immediately after ingestion.
Baseline Reset
Approximately 2 weeks in the absence of further consumption
Half Tolerance
Approximately 1 week
Cross Tolerance

Serotonergic psychedelics

Harm Potential

Addiction & Dependence

Psychological

Extremely Low

25C-NBOH is generally not regarded as habit forming, and repeated use may make taking it again less appealing. Its use is usually self-limiting rather than reinforcing.

Physical

Extremely Low

No evidence of physical dependence or withdrawal symptoms has been documented.

Toxicity

Cardiovascular

Acute cardiovascular effects including elevated blood pressure, increased heart rate, abnormal heartbeat, and vasoconstriction occur during intoxication;citation needed these effects may pose significant risk at higher doses or in individuals with pre-existing cardiovascular conditions.

Thermoregulatory

Temperature regulation suppression and increased body temperature occur during intoxication, which may contribute to dangerous hyperthermia, particularly at high doses or in warm environments with physical activity.citation needed

Psychosis Risk

Anxiety and paranoia appear to occur more readily with 25C-NBOH than with many other psychedelics, possibly related to its stimulating properties. At high doses, confusion, amnesia, and sensory overload may occur, potentially increasing vulnerability to adverse psychological reactions.

Seizure Risk

Seizures are documented as a possible effect.citation needed The unpredictable dose-response relationship of this substance may contribute to seizure risk at unexpectedly high effect levels.

History & Culture

25C-NBOH was first synthesized and documented in 2011 by Martin Hansen at the University of Copenhagen. The compound is a derivative of the phenethylamine psychedelic 2C-C,citation needed distinguished by the addition of an N-benzyl group bearing a hydroxyl substituent on the benzyl

Legality

By Country

Illegal1
United Kingdom flagUnited KingdomClass A
Controlled / restricted3
Brazil flagBrazilControlled (Portaria SVS/MS nº 344)
Germany flagGermanyNpSG (Controlled)
Switzerland flagSwitzerlandControlled (Verzeichnis E)
Not scheduled1
Sweden flagSwedenNot scheduled

References

Source Pages

  1. Bluelight: The Big & Dandy 25C-NBOH Thread
  2. Erowid: 25C-NBOH Experience Vault
  3. Isomer Design (TiHKAL/PiHKAL)
  4. Isomer Design: 25C-NBOH
  5. PsychonautWiki
  6. TripSit Factsheets
  7. Wikipedia

Citations

  1. Martin Hansen, Karina Phonekeo, James S Paine, Sebastian Leth-Petersen, Mikael Begtrup, Hans Bräuner-Osborne, & Jesper L Kristensen. (March 2014). Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience, 5(3), 243–9. https://doi.org/10.1021/cn400216u1
  2. Halberstadt AL, Chatha M, Klein AK, Wallach J, & Brandt SD. (2020). NBOMes-Highly Potent and Toxic Alternatives of LSD. https://doi.org/10.3389/fnins.2020.000781
  3. Agência Nacional de Vigilância Sanitária (ANVISA). (2018-12-10). Resolução da Diretoria Colegiada - RDC Nº 254, DE 10 DE DEZEMBRO DE 2018. Ministério da Saúde / ANVISA. https://bvsms.saude.gov.br/bvs/saudelegis/anvisa/2018/rdc0254_10_12_2018.pdf1
  4. Bundesministerium der Justiz und für Verbraucherschutz. (2016-11-26). Neue-psychoaktive-Stoffe-Gesetz (NpSG). Bundesministerium der Justiz und für Verbraucherschutz. https://www.gesetze-im-internet.de/npsg/BJNR261510016.html1
  5. § 4 NpSG. (2019). https://www.gesetze-im-internet.de/npsg/__4.html1
  6. NIH PubChem structured 25C-NBOH compound properties. pubchem.ncbi.nlm.nih.gov (n.d.). https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/name/25C-NBOH/property/IUPACName,MolecularFormula,CanonicalSMILES/JSON1
  7. NIH PubChem 25C-NBOH synonym record. pubchem.ncbi.nlm.nih.gov (n.d.). https://pubchem.ncbi.nlm.nih.gov/rest/pug/compound/name/25C-NBOH/synonyms/JSON1
  8. Läkemedelsverkets föreskrifter LVFS 2011:10, consolidated narcotics schedules. lakemedelsverket.se (n.d.). https://www.lakemedelsverket.se/globalassets/dokument/lagar-och-regler/lvfs/lvfs-2011-10-konsoliderad.pdf1
  9. Förordning (1992:1554) om kontroll av narkotika. riksdagen.se (n.d.). https://www.riksdagen.se/sv/dokument-och-lagar/dokument/svensk-forfattningssamling/forordning-19921554-om-kontroll-av-narkotika_sfs-1992-1554/1
  10. Förordning (1999:58) om förbud mot vissa hälsofarliga varor. riksdagen.se (n.d.). https://www.riksdagen.se/sv/dokument-och-lagar/dokument/svensk-forfattningssamling/forordning-199958-om-forbud-mot-vissa_sfs-1999-58/1

Further Reading

  1. ChemSpider: 25C-NBOH Chemical Structure
  2. Hansen, M. (2010). Design and Synthesis of Selective Serotonin Receptor Agonists for PET Imaging

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