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{{SummarySheet}}
{{SubstanceBox/DOI}}
{{SubstanceBox/DOI}}
{|
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| ''[[DOI/Summary|Summary sheet: DOI]]''
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'''DOI''', or '''2,5-Dimethoxy-4-iodoamphetamine''', is a [[Psychoactive class::psychedelic]] drug and substituted [[Chemical class::amphetamine]]. Unlike other substituted amphetamines, however, it is not a traditional [[stimulant]].<ref name="DOI TiHKAL">DOI TiHKAL | http://www.erowid.org/library/books_online/pihkal/pihkal067.shtml</ref> It was first synthesized by [[Alexander Shulgin]] in the 1991 book [[PiHKAL]]: A Chemical Love Story. The drug is used recreationally for its [[psychedelic]] and [[entheogen]]ic effects.


DOI's effects have been compared to [[LSD]], although there are differences that experienced users can distinguish. Besides the longer duration, the trip tends to be more [[stimulation|energetic]] than an LSD trip with more body load and a different subjective visual experience. The after effects include residual stimulation and [[wakefulness|difficulty sleeping]], which, depending on the dose, may persist for days.<ref name="DOI TiHKAL"></ref> It is sometimes sold as a substitute for LSD, or even sold falsely as LSD, which may be dangerous because DOI does not have the same established safety profile as LSD.<ref>LSD BLOTTER ACID MIMICS (ACTUALLY CONTAINING
'''2,5-Dimethoxy-4-iodoamphetamine''' (also known as '''DOI''') is a lesser-known [[Psychoactive class::psychedelic]] substance of the [[chemical class::Substituted amphetamines|amphetamine]] class. It is a member of the [[DOx]] family of psychedelic amphetamines.  
4-IODO-2,5-DIMETHOXYAMPHETAMINE (DOI) AND 4-CHLORO-2,5-DIMETHOXYAMPHETAMINE (DOC)) IN LANTANA, FLORIDA | http://web.archive.org/web/20090204025435/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html</ref>


DOI is very well-researched in comparison to many drugs despite being relatively uncommon in terms of its recreational use. This is because it is often used in research as a radioligand and indicator of the presence of [[Serotonin#The 5-HT System|5-HT2A]] [[serotonin]] [[receptor]]s.
The synthesis of DOI was first described in 1972<ref name="Coutts1973">{{cite journal|last1=Coutts|first1=R. T.|last2=Malicky|first2=J. L.|year=1973|title=The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)|journal=Canadian Journal of Chemistry|volume=51|issue=9|pages=1402-1409|doi=10.1139/v73-210|issn=0008-4042|eissn=1480-3291|oclc=02248672}}</ref><ref name="Zamberlan2018">{{cite journal|title=The Varieties of the Psychedelic Experience: A Preliminary Study of the Association Between the Reported Subjective Effects and the Binding Affinity Profiles of Substituted Phenethylamines and Tryptamines|year=2018|doi-access=free|first1=F.|last1=Zamberlan|first2=C.|last2=Sanz|first3=R. M.|last3=Vivot|first4=C.|last4=Pallavicini|first5=F.|last5=Erowid|first6=E.|last6=Erowid|first7=E.|last7=Tagliazucchi|pmc=6235949|pmid=30467466|doi=10.3389/fnint.2018.00054|volume=12|issue=54|journal=Frontiers in Integrative Neuroscience|eissn=1662-5145|oclc=1132048937}}</ref> and its usage in humans was first documented by [[Alexander Shulgin]] in the 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").{{citation needed}} DOI is very well-researched compared to most psychedelics. It is regularly used in research as a radioligand to map [[Serotonin#The 5-HT System|serotonin-2A]] [[receptors]] in the brain.{{citation needed}}
 
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 [[wakefulness|difficulty sleeping]], which, depending on the dose and time taken during the day, may persist for days afterwards.
 
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.<ref>{{cite web|title=LSD Blotter Acid Mimics (Actually Containing 4-Iodo-2,5-dimethoxyamphetamine (DOI) And 4-Chloro-2,5-dimethoxyamphetamine (DOC)) In Lantana, Florida|archive-url=http://web.archive.org/web/20090204025435/http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html|url=http://www.usdoj.gov/dea/programs/forensicsci/microgram/mg0608/mg0608.html|archive-date=February 4, 2009|work=Microgram Bulletin|publisher=Drug Enforcement Administration (DEA)|date=June 2008|oclc=54464390}}</ref>
 
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 experienced with [[psychedelics]]. 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.
 
==History and culture==
{{historyStub}}
 
DOI was first synthesized by a team at the University of Alberta in 1972.<ref name="Coutts1973"/><ref name="Zamberlan2018"/>


==Chemistry==
==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 (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOI contains methoxy functional groups CH<sub>3</sub>O- attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as an iodine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOI is the amphetamine, or alpha-methylated analogue, of the phenethylamine [[2C-I]].<ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=67</ref>
DOI, or 2,5-Dimethoxy-4-iodoamphetamine, is a molecule of the [[Substituted amphetamines|amphetamine]] class. Amphetamines are substituted [[phenethylamines]] containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOI contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as an iodine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOI is the amphetamine, or alpha-methylated analogue, of the phenethylamine [[2C-I]].<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal067.shtml|chapter=#67. DOI}}</ref>


==Pharmacology==
==Pharmacology==
{{Main|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
DOI's [[psychedelic]] effects are believed to come from its efficacy as an [[agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2A</sub>]], [[Serotonin#The 5-HT System|5-HT<sub>2B</sub>]] and [[Serotonin#The 5-HT System|5-HT<sub>2C</sub>]] [[receptor]]s.<ref name="head twitch">Head-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 | https://www.ncbi.nlm.nih.gov/pubmed/22517680</ref> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.  
DOI's [[psychedelic]] effects are believed to come from its efficacy as an [[agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2A</sub>]], [[Serotonin#The 5-HT System|5-HT<sub>2B</sub>]] and [[Serotonin#The 5-HT System|5-HT<sub>2C</sub>]] [[receptor]]s.<ref name="head twitch">{{cite journal|title=Head-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|pmid=22517680|pmc=3722587|doi=10.1002/dta.1333|first1=C. E.|last1=Canal|first2=D.|last2=Morgan|year=2012|volume=4|issue=7-8|pages=556-576|issn=1942-7603|eissn=1942-7611|oclc=231680670|journal=Drug Testing and Analysis}}</ref> 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-HT<sub>2A</sub> agonists an entirely new area for development of novel treatments for these conditions.<ref>{{cite journal|title=Serotonin 5-Hydroxytryptamine<sub>2A</sub> Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency|pmid=18708586|doi=10.1124/jpet.108.143461|first1=B.|last1=Yu|first2=J.|last2=Becnel|first3=M.|last3=Zerfaoui|first4=R.|last4=Rohatgi|first5=A. H.|last5=Boulares|first6=C. D.|last6=Nichols|journal=Journal of Pharmacology and Experimental Therapeutics|year=2008|volume=327|issue=2|pages=316-323|issn=0022-3565|eissn=1521-0103|oclc=1606914}}</ref>
{| class="wikitable" style="width:60%;"
|+ Binding Profile of DOI and its isomers
! Receptor !! width = 50px | K<sub>i</sub> (racemic DOI)<ref name="PDSP">Roth, 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</ref> !! width = 50px | K<sub>i</sub> (''R''-DOI)<ref name="PDSP"></ref> !! width = 100px | K<sub>i</sub> (''S''-DOI)<ref name="PDSP"></ref> !! Intrinsic activity<ref name="head twitch"></ref>
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 2355 nM || 3843 nM || ND || ND
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 1261 nM || ND || ND || ND
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 1241.3 nM || ND || ND || ND
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 2970 nM || ND || ND || ND
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || 2125.44 nM || ND || ND || ND
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 0.68 nM || 0.65 nM || 0.65 nM || Partial agonist.
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 20.03 nM || 53.70318 nM || 28.183829 nM || Partial agonist/full agonist
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 2.38 nM || 5.370318 nM || 8.317638 nM || Full agonist when coupled to [[phospholipase A]]. Partial agonist (intrinsic efficacy = 53%) when coupled to [[phospholipase C]].
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || 1000 nM || ND || ND || ND
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || 1000 nM || ND || ND || ND
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || >10000 nM || ND || ND || ND
|}


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-HT<sub>2A</sub> agonists an entirely new area for development of novel treatments for these conditions.<ref>Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency | Journal of Pharmacology and Experimental Therapeutics | https://www.ncbi.nlm.nih.gov/pubmed/18708586 </ref>
DOI has also been shown to induce rapid growth and reorganization of dendritic spines and synaptic connections with other [[neurons]], processes known to underlie neuroplasticity.<ref>{{cite journal|last1=Jones|first1=K. A.|last2=Srivastava|first2=D. P.|last3=Allen|first3=J. A.|last4=Strachan|first4=R. T.|last5=Roth|first5=B. L.|last6=Penzes|first6=P.|year=2009|title=Rapid modulation of spine morphology by the 5-HT<sub>2A</sub> serotonin receptor through kalirin-7 signaling|journal=Proceedings of the National Academy of Sciences|volume=106|issue=46|pages=19575-19580|pmid=19889983|doi=10.1073/pnas.0905884106|pmc=2780750|issn=0027-8424|eissn=1091-6490|oclc=43473694|doi-access=free}}</ref>


DOI has also been shown to induce rapid growth and reorganization of [[dendritic spines]] and [[synapse|synaptic]] connections with other [[neurons]], processes known to underlie [[neuroplasticity]].<ref>{{Cite web |title=Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling. |journal=Journal of Pharmacology and Experimental Therapeutics | publisher = Department of Physiology, Northwestern University Feinberg School of Medicine, Chicago, IL 60611, USA | date = 17 November 2009 |doi=10.1073/pnas.0905884106 |pmid=19889983|url=https://www.ncbi.nlm.nih.gov/pubmed/19889983 }}</ref>
A study demonstrated that DOI, [[DMT]], [[LSD]], and noribogaine (a metabolite of [[ibogaine]]) promote neuritogenesis both ''in vitro'' and ''in vivo''.<ref>{{cite journal|title=Psychedelics Promote Structural and Functional Neural Plasticity|first1=C.|last1=Ly|first2=A. C.|last2=Greb|first3=L. P.|last3=Cameron|first4=J. M.|last4=Wong|first5=E. V.|last5=Barragan|first6=P. C.|last6=Wilson|first7=K. F.|last7=Burbach|first8=S. S.|last8=Zarandi|first9=A.|last9=Sood|first10=M. R.|last10=Paddy|first11=W. C.|last11=Duim|first12=M. Y.|last12=Dennis|first13=A. K.|last13=McAllister |first14=K. M.|last14=Ori-McKenney|first15=J. A.|last15=Gray|first16=D. E.|last16=Olson|year=2018|volume=23|issue=11|pages=3170-3182|doi=10.1016/j.celrep.2018.05.022|pmc=6082376|pmid=29898390|doi-access=free|issn=2211-1247|journal=Cell Reports}}</ref>


==Subjective effects==
==Subjective effects==
{{effectStub}}
{{Preamble/SubjectiveEffects}}
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of effects.
{{effects/base
===Physical effects===
 
*'''[[Effect::Spontaneous tactile sensations]]'''
|{{effects/physical|
*'''[[Effect::Physical euphoria|Euphoria]]'''
*'''[[Effect::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 becoming 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.
*'''[[Effect::Stimulation]]'''
*'''[[Effect::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.
*'''[[Effect::Nausea]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensation are consistently reported at low to moderate levels throughout most DOI experiences.
*'''[[Effect::Temperature regulation loss]]'''
*'''[[Effect::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.
*'''[[Effect::Increased heart rate]]'''
*'''[[Effect::Increased blood pressure]]'''{{citation needed}}
*'''[[Effect::Increased heart rate]]'''{{citation needed}}
*'''[[Effect::Muscle contractions]]'''
*'''[[Effect::Muscle spasms]]'''
*'''[[Effect::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.
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Increased salivation]]'''
*'''[[Effect::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}}


===Cognitive effects===
}}
*'''[[Effect::Empathy, love and sociability enhancement]]'''
{{effects/visual|
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Memory suppression]]'''
*'''[[Effect::Ego death]]'''
*'''[[Effect::Unity and interconnectedness]]'''
*'''[[Effect::Wakefulness]]'''
 
===Visual effects===
====Enhancements====
====Enhancements====
*'''[[Effect::Visual acuity enhancement|Acuity enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Colour enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
*'''[[Effect::Pattern recognition enhancement]]'''
*'''[[Effect::Visual acuity enhancement]]'''


====Distortions====
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting#morphing|morphing]])''
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Brightness alteration]]'''
*'''[[Effect::Scenery slicing]]'''
*'''[[Effect::Diffraction]]'''


====[[Effect::Geometry]]====
====Hallucinatory states====
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 [[psychedelic]]s. This holds particularly true in comparison to other substances within the [[phenethylamine]] class. These effects include:


====Hallucinatory states====
*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - In comparison to other [[psychedelic]]s such as [[LSD]], DOI is extremely high in internal hallucinations. They are more common within dark environments and can be comprehensibly described through its [[Internal_hallucinations#Variations|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.
*'''[[Effect:: 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.
 
}}
|{{effects/cognitive|
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:


===Auditory effects===
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought connectivity]]'''
*'''[[Effect::Anxiety]]''' & '''[[Effect::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|"bad trip"]].
*'''[[Effect::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.
*'''[[Effect::Cognitive euphoria]]'''
*'''[[Effect::Delusion]]'''
*'''[[Effect::Analysis enhancement]]''' - This effect is consistent in its manifestation and [[outrospection]] dominant.
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Novelty enhancement]]'''
*'''[[Effect::Personal bias suppression]]'''
*'''[[Effect::Personal meaning enhancement]]'''
*'''[[Effect::Immersion enhancement]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased sense of humor]]'''
**'''[[Effect::Laughter fits]]''' - This can manifest prominently during a DOI experience, particularly during the [[Duration#Come up|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.
*'''[[Effect::Memory suppression]]'''
**'''[[Effect::Ego death]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Wakefulness]]'''
 
}}
{{effects/auditory|
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory enhancement|Enhancements]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory distortion|Distortions]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
*'''[[Effect::Auditory hallucinations|Hallucinations]]'''
}}
{{effects/multisensory|
*'''[[Effect::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.
}}
{{effects/transpersonal|
*'''[[Effect::Existential self-realization]]'''
*'''[[Effect::Unity and interconnectedness]]'''
}}
}}
===Experience reports===
Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
{{#ask: [[Category:DOI]][[Category:Experience]]|format=ul|Columns=1}}
Additional experience reports can be found here:
*[https://www.erowid.org/experiences/subs/exp_DOI.shtml Erowid Experience Vaults: DOI]


==Toxicity and harm potential==
==Toxicity and harm potential==
{{Main|Research chemicals#Toxicity and harm potential}}
{{toxicity}}
The toxicity and long-term health effects of recreational DOI do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because DOI is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried DOI suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
The toxicity and long-term health effects of recreational DOI do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because DOI is a [[research chemical]] with very little history of human usage.  
 
Anecdotal reports from users suggests that there are no negative health effects attributed to simply trying it by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
 
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
 
===Overdose===
{{DOxOD}}
 
===Tolerance and addiction potential===
===Tolerance and addiction potential===
DOI is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating.  
DOI is [[Addiction potential::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 [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 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.
Tolerance to the effects of DOI is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::5-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::10-14 days]] to be back at baseline (in the absence of further consumption). DOI presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of DOI all psychedelics will have a reduced effect.


==Legal issues==
===Dangerous interactions===
*'''Australia''' - The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.<ref>Therapeutic Goods Administration. Australian Government Department of Health and Ageing | http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699</ref>
{{DangerousInteractions/Intro}}
*'''Canada''' - DOI is listed as a Schedule 1<ref>Canadian Legal Information Institute (CanLII). Controlled Drugs and Substances Act, S.C. 1996, c. 19, as amended | http://isomerdesign.com/Cdsa/schedule.php?schedule=1&section=18.5&structure=C</ref> drug as it is an analogue of amphetamine.<ref>Canadian Legal Information Institute (CanLII). Controlled Drugs and Substances Act, S.C. 1996, c. 19, as amended | http://isomerdesign.com/Cdsa/definitions.php?structure=C</ref> The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
{{DangerousInteractions/Psychedelics}}
*'''Denmark''' - It has been illegal since April 8, 2007.<ref>DOC Legal Status by Erowid |
http://www.erowid.org/chemicals/doc/doc_law.shtml</ref>
*'''Latvia:''' DOI is a Schedule I controlled substance.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</ref>
*'''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.<ref>Läkemedelsverkets författningssamling | http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf</ref>
*'''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.<ref>The 2015 Florida Statutes Title XLVI CRIMES Chapter 893 DRUG ABUSE PREVENTION AND CONTROL | http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html</ref>


==Legal status==
*'''Australia''': DOI is not listed as a prohibited substance in The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP).<ref>{{cite web|title=Poisons Standard 2013|date=July 22, 2013|publisher=Therapeutic Goods Administration|url=http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699|id=F2013L01607|isbn=978-1-74241-895-7|type=PDF}}</ref>
*'''Austria''': DOI is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
*'''Brazil''': DOI is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|language=pt|access-date=January 8, 2020|publisher=Agência Nacional de Vigilância Sanitária (Anvisa) [National Sanitary Surveillance Agency]|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7}}</ref>
*'''Canada''': DOI is listed as a Schedule 1  drug as it is an analogue of amphetamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3&section=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref> The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
*'''Denmark''': DOI became illegal on April 8, 2007.{{citation needed}}
*'''Germany''': DOI is controlled under Anlage II BtMG<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_ii.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage II|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> (''Narcotics Act, Schedule II'') as of December 13, 2014.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 2014 Teil I Nr. 57|page=1999-2002|publication-date=December 12, 2014|language=de|oclc=231871244|issn=0341-1095|date=December 5, 2014}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref>
*'''Latvia''': DOI is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref>
*'''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.<ref>{{cite web|url=http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf|archive-url=https://web.archive.org/web/20200924055555/https://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf|archive-date=August 1, 2019|title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika|date=August  14, 2007|id=LVFS 2007:10|publication-date=August 30, 2007|issn=1101-5225|publisher=Läkemedelsverket [Medical Products Agency ]|language=sv}}</ref>
*'''Switzerland''': DOI can be considered a controlled substance as a defined derivative of a-Methylphenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''Turkey:''' DOI is a classed as drug and is illegal to possess, produce, supply, or import.<ref>{{cite web|title=Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr}}</ref><ref>{{cite web|title=Kararnamenin Eki: Liste|url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf|publisher=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication]|publication-date=January 25, 2014|date=December 16, 2013|language=tr|id=2013/5742|work=Resmî Gazete, Sayı: 28893}}</ref>
*'''United Kingdom''': DOI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>{{cite web|url=http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted|title=Psychoactive Substances Act 2016|access-date=January 1, 2020|publisher=UK Government}}</ref>
*'''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.{{citation needed}}
**'''Florida''': DOI is a Schedule I controlled substance in the state of Florida.<ref>{{cite web|title=The 2015 Florida Statutes - Chapter 893|url=http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html|publisher=The Florida Legislature|access-date=July 18, 2020}}</ref>
==See also==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Psychedelics]]
*[[Psychedelic]]
*[[Phenethylamines]]
*[[Phenethylamine]]
*[[DOx]]
*[[DOM]]
*[[DOC]]
*[[DOC]]
==External links==
==External links==
*[https://en.wikipedia.org/wiki/2,5-Dimethoxy-4-iodoamphetamine DOI (Wikipedia)]
*[https://en.wikipedia.org/wiki/2,5-Dimethoxy-4-iodoamphetamine DOI (Wikipedia)]
*[http://isomerdesign.com/PiHKAL/read.php?id=67 DOI (PiHKAL)]
*[https://erowid.org/chemicals/doi/doi.shtml DOI (Erowid Vault)]
*[http://drugs.tripsit.me/doi DOI (TripSit)]
*[http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=67 DOI (PiHKAL / Isomer Design)]
*[http://www.bluelight.org/vb/threads/224091-The-Big-and-Dandy-DOI-Thread DOI (Bluelight)]
 
*[https://www.erowid.org/experiences/subs/exp_DOI.shtml DOI experiences (Erowid)]
===Discussion===
*[http://www.bluelight.org/vb/threads/224091-The-Big-and-Dandy-DOI-Thread The Big & Dandy DOI Thread (Bluelight)]


==References==
==References==
<references/>
{{reflist|2}}


[[Category:Amphetamine]]
[[Category:Psychoactive substance]]
[[Category:Psychedelic]]
[[Category:Psychedelic]]
[[Category:Substance]]
[[Category:DOx]]
[[Category:Psychoactive substance]]
 
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