25I-NBOH may result in severe injury or death.
While no deaths have been reported, it is likely that this compound shares a similar toxicity profile with 25I-NBOMe (which has been linked to multiple deaths). It is strongly discouraged to take higher doses of this substance or to insufflate (snort) it. Please see this section for more details.
|Summary sheet: 25I-NBOH|
|Molecular structure of 25I-NBOH|
|Common names||25i-NBOH, Cimbi-27|
|Routes of Administration|
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 suggest that this substance may be difficult to use safely due to its highly sensitive dose-response and unpredictable effects.
- 1 Chemistry
- 2 Pharmacology
- 3 Subjective effects
- 4 Toxicity and harm potential
- 5 Legality
- 6 See also
- 7 External links
- 8 References
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.
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.
|| This subjective effect breakdown is a stub.|
As such, it may contain incomplete or wrong information and is still in progress.
You can help by expanding it.
The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki contributors. The listed effects should be taken with a grain of salt and will rarely (if ever) occur all at once, but heavier doses will increase the chances and are more likely to induce a full range of effects. Likewise, adverse effects become much more likely on higher doses and may include injury or death.
- Stimulation - In terms of its effects on the physical energy levels of the user, 25I-NBOH is usually considered to be very energetic and stimulating. For most people, this substance induces a unique type of physical stimulation which can be described as feeling extremely energetic but in a way which does not force the tripper to move unless they genuinely choose to do so. For others, however, the stimulation can be quite uncontrollable, occasionally resulting in bodily shakes and a grinding of the teeth comparable to that of MDMA and traditional stimulants such as amphetamine.
- Perception of bodily lightness - In terms of the body’s perceived weight, this substance consistently leaves people feeling extremely light, often to the point of total weightlessness.
- Spontaneous physical sensations - The "body high" itself can be described as a mild, all-encompassing, soft but euphoric tingling sensation. This tingling sensation is also accompanied by spontaneous rushes of euphoria that become longer and more drawn out proportional to the dosage consumed.
- Mouth numbing - Assuming the substance has been taken sublingually, the very first physical effect which a person will notice immediately after sublingual absorption is a strong, unpleasant metallic chemical taste. This is accompanied by a very distinct feeling of general numbness of the tongue and mouth which can stay for up to an hour after the blotter paper has been consumed.
- Nausea - As the user begins to come up, nausea is not uncommon and can sometimes result in initial vomiting, although nausea usually disappears when the user has vomited or the trip fully set in. In comparison to other psychedelics such as psilocin, LSD, 2C-E and 2C-I, this could actually be considered very mild in its intensity.
- Temperature regulation suppression
- Abnormal heartbeat
- Increased heart rate
- Increased blood pressure
- Muscle contractions
- Muscle cramps
- Muscle tension
- Gustatory hallucinations
- Appetite suppression
- Stomach cramps
- Dry mouth
- Difficulty urinating or Frequent urination
- Restless legs
- Pupil dilation
- Visual acuity enhancement
- Colour enhancement
- Pattern recognition enhancement
- Magnification - At higher doses, users can experience a "fish-eye" effect, where magnification changes based on the direction the user is looking relative to the object.
- Drifting (melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and unrealistic/cartoon-like in style.
- Colour shifting
- Colour replacement
- Colour tinting
- Depth perception distortions
- Perspective distortions
- Brightness alteration
- After images
- Symmetrical texture repetition
- Scenery slicing
The visual geometry produced by this substance is similar to LSD and can be comprehensively described as algorithmic in geometric style, intricate in complexity, fine and zoomed out in detail, fast and smooth in motion, structured in shape, colorful in scheme, glossy in color, sharp around the edges and equally angular as well as rounded across their corners. In comparison to other more commonly used psychedelics they can be described as significantly more intricate than the visual geometry found within 2C-I and most of the 2C-x family in general as well as completely on par with LSD, Psilocin and DMT at appropriately high dosages.
25I-NBOH’s geometry leads reliably leads to Level 8A visual geometry with Level 8B remaining so far unconfirmed. It seems to consistently be able to build up in visual intensity when the user stares at a central point. This eventually envelops the visual field and creates the sensation that the tripper has broken through into a continuously shifting geometric landscape or structure with a vast sense of immersive physical size attributed to it.
25I-NBOH is capable of producing a full range of hallucinatory states within the level 1 - 3 range extremely consistently. However, level 4 hallucinatory breakthroughs are reported but very different and inconsistent in comparison to other more commonly used psychedelics such as psilocin, 2C-E and DMT.
These effects include:
- Machinescapes - This component is an uncommon effect that typically only occurs at very strong to heavy doses. It also tends to be accompanied by overwhelming if not dangerous physical and cognitive effects.
- Internal hallucinations - (settings, sceneries, and landscapes; alterations in perspective and scenarios and plots). These are more common within dark environments and can be described as lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
The cognitive effects of 25I-NBOH are described by many as notably light in comparison to the classical psychedelics. It is not uncommon for people to report feeling that their thought stream has maintained general normality in its specific style throughout low to moderate dosages. At high dosages, however, strong to overwhelming cognitive alterations become present, which can lead to states of confusion, amnesia, and general sensory overload.
The most prominent of these cognitive effects generally include:
- Analysis enhancement - This effect is generally only present at low doses.
- Thought acceleration and Thought deceleration - Although one of 25I-NBOH's effects is thought acceleration, the opposite may occur at higher doses.
- Conceptual thinking - This effect is considered to be very mild compared to traditional psychedlics.
- Anxiety & Paranoia - This effect seems to occur more readily than other psychedelics, perhaps due to its very prominent stimulating properties
- Feelings of impending doom - This is generally only experienced during the comedown period or if one has taken a large amount of the substance.
- Empathy, affection, and sociability enhancement - The entactogenic effects range from mild to powerful, but are inconsistently manifested. Entactogenic effects for people who try this substance usually become prominent in the presence of others. These feelings of increased sociability, love and empathy do not seem to be quite as strong or profound as those found within other entactogens (such as MDMA, 2C-B and AMT)
- Memory suppression
- Novelty enhancement
- Immersion enhancement
- Emotionality enhancement
- Increased sense of humor
- Increased music appreciation
- Personal bias suppression
- Increased libido
- Time distortion
- Dosage independent intensity - While the reasons for this are not understood, many reports suggest that this substance can produce unexpectedly strong or weak effects even when taken at the seemingly same dose in an unpredictable manner. This may contribute to the relative risk it is poses compared to most other psychedelics.
- Synaesthesia - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
- While they are occasionally reported, the transpersonal effects produced by this substance seem to be significantly less consistent and reproducible than other psychedelics, which perhaps corresponds with the notably mild changes to one's perceptual and cognitive processes.
Anecdotal reports which describe the effects of this compound within our experience index include:
Additional experience reports can be found here:
Toxicity and harm potential
This toxicity and harm potential section is a stub.
As such, it may contain incomplete or even dangerously wrong information. You can help by expanding upon or correcting it.
25I-NBOH is a relatively new substance, and little is known about its toxicity or interaction with other substances. It is assumed to pose similar acute health risks as 25I-NBOMe (see this section for more information). The LD50 has not yet been determined although it is likely to be potentially fatal at heavy dosages.
25I-NBOH's extreme potency means it should not be insufflated (snorted) as this method of administration has been associated with many deaths and hospitalizations with the closely related 25I-NBOMe.
Tolerance and addiction potential
25I-NBOH is not habit-forming and the desire to use it can actually decrease with use. It is most often self-regulating.
Tolerance to the effects of 25I-NBOH is built almost immediately after ingestion. After that, it takes about 1 week for the tolerance to be reduced to half and 2 weeks to be back at baseline (in the absence of further consumption). 25I-NBOH presents cross-tolerance with all psychedelics, meaning that after the consumption of 25I-NBOH all psychedelics will have a reduced effect.
Although many psychoactive substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially dangerous combinations, but may not include all of them. Certain combinations may be safe in low doses of each but still increase the potential risk of death. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
- Tramadol - Tramadol lowers the seizure threshold and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.
- Stimulants - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable anxiety, panic, thought loops and paranoia. This interaction may cause elevated risk of psychosis.
- Lithium - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its glutaminergic and GABAergic effects.
This legality section is a stub.
As such, it may contain incomplete or wrong information. You can help by expanding it.
- United Kingdom - 25I-NBOH is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.
- Sweden: The Riksdag added 25I-NBOH to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of August 18, 2015, published by Medical Products Agency (MPA) in regulation HSLF-FS 2015:12
- 25I-NBOMe (2C-I-NBOMe) Fatalities / Deaths by Erowid | https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml
- Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. PMID 21174090. https://doi.org/10.1007/s00259-010-1686-8
- Silva, M. E.; Heim, R.; Strasser, A.; Elz, S.; Dove, S. (2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. PMID 21088982. https://doi.org/10.1007/s10822-010-9400-2
- Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. PMC 3963123. PMID 24397362. https://doi.org/10.1021/cn400216u
- Talaie, H., Panahandeh, R., Fayaznouri, M. R., Asadi, Z., & Abdollahi, M. (2009). Dose-independent occurrence of seizure with tramadol. Journal of medical toxicology, 5(2), 63-67. doi:10.1007/BF03161089
- United Kingdom. (2014). Misuse of Drugs Act 1971 (S.I. 2014/1106). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/2014/1106/made