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DOI
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Revision as of 09:50, 14 April 2018 by >Dextromethorphan(minor edits)
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
2,5-Dimethoxy-4-iodoamphetamine (abbreviated DOI) is a lesser-known psychedelic substance of the phenethylamine class that produces long-lived psychedelic effects when administered. It is a member of the DOx family of psychedelic amphetamines.
The synthesis of DOI was first reported in 1972.[1] Its usage in humans was first documented by Alexander Shulgin in the 1991 book PiHKAL ("Phenethylamines I Have Known and Loved").
DOI is very well-researched compared to most psychedelics. It is often used in research as a radioligand and indicator of the presence of serotonin-2Areceptors.
The effects of DOI are often compared to those of LSD, although notable differences can be distinguished. Besides the significantly longer duration, the experience is commonly reported to be more stimulating than LSD, with a more pronounced body load and a less complex head space. The after effects include long-lasting residual stimulation and difficulty sleeping, which, depending on the dose and time taken during the day, may persist for days afterwards.[2]
DOI is sometimes sold as a substitute for LSD, or even sold falsely as LSD. This can be dangerous because DOI does not have the same established safety profile as LSD.[3]
Today, DOI finds rare use as a recreational drug and an entheogen and is rarely sold if not inexistent on the streets (unless in the form of misrepresented LSD). Along with its sensitive dose-response and unusually long duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with hallucinogens. Therefore it is highly advised to approach this highly dose-sensitive, and long-lasting psychedelic substance with the proper amount of precaution and harm reduction practices if using it.
As a result, it may contain incomplete or wrong information. You can help by expanding it.
DOI was first synthesized by a team at the University of Alberta in 1972.[4]
Chemistry
DOI, or 2,5-Dimethoxy-4-iodoamphetamine, is a molecule of the amphetamine class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH2) group through an ethyl chain and a methyl group bound to the alpha carbon Rα. DOI contains methoxy functional groups OCH3 attached to carbons R2 and R5 as well as an iodine atom attached to carbon R4 of the phenyl ring. DOI is the amphetamine, or alpha-methylated analogue, of the phenethylamine 2C-I.[5]
DOI's psychedelic effects are believed to come from its efficacy as an agonist at the 5-HT2A, 5-HT2B and 5-HT2Creceptors.[6] However, the role of these interactions and how they result in the psychedelic experience continues to remain the subject of ongoing scientific inquiry.
DOI and its isomers binding profiles to specific 5HT receptor sets can be seen in the chart below:
Besides its action as a psychedelic, DOI has been shown to be an extremely potent inhibitor of tumour necrosis factor-alpha inflammation at picomolar concentrations in cell studies. TNF-alpha is an important target for research into degenerative conditions such as rheumatoid arthritis and Alzheimer's disease where the disease process involves tissue damage through chronic inflammation. This could make DOI and other 5-HT2A agonists an entirely new area for development of novel treatments for these conditions.[8]
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects
Stimulation - In terms of its effects on the physical energy levels of the user, DOI is usually considered to be extremely stimulating at levels which are capable of become uncomfortable and overwhelming. This can result in a shakiness and unsteadiness of the hands but encouraging one to move around, run, dance, climb and generally engage in physical activities. In comparison, other more commonly used psychedelics such as psilocin are generally sedating and relaxed.
Spontaneous physical sensations - The "body high" of DOI often described as being notably more intense in comparison to most classical psychedelics such as LSD. The sensation itself can be described as a constantly present yet somewhat mild energetic pins and needles sensation that encompasses a person’s entire body. It is usually felt over every square inch of the skin but occasionally manifests itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves. However, this effect is reported to be very dose-dependent, as even slight increases in one's dose can result in persisting unpleasant feelings of over-stimulation.
Physical euphoria - It should be noted that this effect is not as reliably induceable as it is with substances like stimulants or entactogens, and can just as easily manifest as physical discomfort without any apparent reason.
Tactile enhancement - Feelings of enhanced tactile sensation are consistently reported at low to moderate levels throughout most DOI experiences.
Nausea - Mild to extreme nausea is reported when consumed in moderate to high dosages and either passes once the person has vomited or gradually fades by itself as the peak sets in.
Vasoconstriction[citation needed] - This effect is usually only present at higher dosages, but can be particularly uncomfortable when it manifests, and may persist throughout the main duration of the experience.
Seizure - This is a rarely observed effect but is known to happen in those who are presumably predisposed to them, especially while in physically taxing conditions such as being dehydrated, undernourished, overheated, or generally fatigued.[citation needed]
DOI and other psychedelic substituted amphetamines produce a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. This holds particularly true in comparison to other substances within the phenethylamine class. These effects include:
Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - In comparison to other psychedelics such as LSD, DOI is extremely high in internal hallucinations. They are more common within dark environments and can be comprehensibly described through its variations as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
External hallucinations - These are often present during the comedown and can include shadow people, among other indescribable beings. These external hallucinations are often lucid, interactive, autonomous, and robust. As sleep deprivation and stimulant psychosis surface, a trip sitter should accompany individuals sensitive to stimulants for the last part of the comedown. The visual effects of psychosis have been reported to blend into the psychedelic visuals around the 16-24 hour mark, sometimes accompanied by auditory hallucinations.
Cognitive effects
The cognitive effects of DOI are described by many as characterized as extreme mental stimulation combined with a powerful amplification of the user's current mental state.
The total sum of these cognitive components regardless of the setting generally includes:
Anxiety & Paranoia - This effect is not as common at low to moderate doses and is less likely to occur when the basic rules of set and setting are taken into account. It should be noted that this inconsistently induced effect is seemingly more likely to manifest when used with cannabis. This combination should be used with extreme caution if one is not experienced with psychedelics, meaning that the user should adequately pace themselves with a fraction of their usual amount. It is commonly reported that psychedelics can to a certain extent counteract some of the perceived mental cloudiness or intoxicating effects of THC causing the user to in turn use more cannabis than is needed which can often lead to an overwhelmingly anxious and paranoid headspace which can trigger a "bad trip".
Empathy, affection, and sociability enhancement - This component is typically manifested only in the context of social settings in which one is within the company of others, and only at lower, non-impairing doses. These feelings of sociability, affection and empathy tend to be weaker and less consistent than those found on substances such as MDMA and 2C-B, but can still prove strong enough to provide long-lasting therapeutic effects.
Laughter fits - This can manifest prominently during a DOI experience, particularly during the come up phase, often resulting in bouts of uncontrollable giggles and laughter that can form a feedback loop if around others who are also under the influence.
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.
The toxicity and long-term health effects of recreational DOI do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because DOI is a research chemical with very little history of human usage. Anecdotal evidence from those within the community who have tried DOI suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
DOI 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 DOI are built almost immediately after ingestion. After that, it takes about 5-7 days for the tolerance to be reduced to half and 10-14 days to be back at baseline (in the absence of further consumption). DOI presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of DOI all psychedelics will have a reduced effect.
Although many 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 relatively harmless in low doses of each but can still increase the risk of unpredictable injury or 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[10] and psychedelics may act as triggers for seizures, particularly in those who are predisposed to them.[citation needed]
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.[citation needed]
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.[citation needed]
As such, it may contain incomplete or wrong information. You can help by expanding it.
Australia - The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[11]
Brazil - Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.[12]
Canada - DOI is listed as a Schedule 1[13] drug as it is an analogue of amphetamine.[14] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
Denmark - It has been illegal since April 8, 2007.
Latvia - DOI is a Schedule I controlled substance.[15]
Sweden - DOI is a Schedule I substance as of August 30, 2007; this was published by the Medical Products Agency in their regulation LVFS 2007:10.[16]
United Kingdom - It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.[17]
United States - DOI is not scheduled in the United States, but it is likely that it would be considered an analog (of DOB) in which case sales or possession could be prosecuted under the Federal Analogue Act. DOI is regularly used in animal and in vitro research. Scheduling DOI could cause problems for medical researchers.
Florida - DOI is a Schedule I controlled substance in the state of Florida.[18]
Coutts, R. T., & Malicky, J. L. (1973). The synthesis of some analogs of the hallucinogen 1-(2, 5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Canadian Journal of Chemistry, 51(9), 1402-1409. https://doi.org/10.1139/v73-210
References
↑Coutts, R. T., & Malicky, J. L. (1973). The synthesis of some analogs of the hallucinogen 1-(2, 5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Canadian Journal of Chemistry, 51(9), 1402-1409. https://doi.org/10.1139/v73-210
↑Cite error: Invalid <ref> tag; no text was provided for refs named DOI TiHKAL
↑Coutts, R. T., & Malicky, J. L. (1973). The synthesis of some analogs of the hallucinogen 1-(2, 5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM). Canadian Journal of Chemistry, 51(9), 1402-1409. https://doi.org/10.1139/v73-210
↑ 6.06.1Head-twitch response in rodents induced by the hallucinogen 2,5-dimethoxy-4-iodoamphetamine: a comprehensive history, a re-evaluation of mechanisms, and its utility as a model (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/22517680
↑ 7.07.17.2Roth, BL; Driscol, J (12 January 2011). "PDSP Ki Database". Psychoactive Drug Screening Program (PDSP). University of North Carolina at Chapel Hill and the United States National Institute of Mental Health. Retrieved 4 March 2014. | http://pdsp.med.unc.edu/pdsp.php
↑Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency | Journal of Pharmacology and Experimental Therapeutics (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/18708586
↑Jones, K. A., Srivastava, D. P., Allen, J. A., Strachan, R. T., Roth, B. L., & Penzes, P. (2009). Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling. Proceedings of the National Academy of Sciences, 106(46), 19575-19580. PMID: 19889983. https://doi.org/10.1073/pnas.0905884106
↑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
↑Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086
