DOI - PsychonautWiki

DOI

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Summary sheet: DOI
DOI
DOI.svg
Chemical Nomenclature
Common names DOI
Substitutive name 2,5-Dimethoxy-4-iodoamphetamine
Systematic name 1-(4-Iodo-2,5-dimethoxyphenyl)-2-propanamine
Class Membership
Psychoactive class Psychedelic
Chemical class Amphetamine
Routes of Administration

WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.



⇣ Oral
Dosage
Threshold 0.5 mg
Light 0.5 - 1 mg
Common 1 - 2 mg
Strong 2 - 3 mg
Heavy 3 mg +
Duration
Total 16 - 24 hours
Onset 1 - 2 hours
Come up 1.5 - 3 hours









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.

Interactions
Cannabis
Stimulants
Tramadol
Lithium


2,5-Dimethoxy-4-iodoamphetamine (also known as DOI) is a lesser-known psychedelic substance of the amphetamine class. It is a member of the DOx family of psychedelic amphetamines.

The synthesis of DOI was first described in 1972[1][2] 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-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 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.[3]

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

 

This History and culture section is a stub.

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.[1][2]

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.[4]

Pharmacology

Further information: Serotonergic psychedelic

DOI's psychedelic effects are believed to come from its efficacy as an agonist at the 5-HT2A, 5-HT2B and 5-HT2C receptors.[5] However, the role of these interactions and how they result in the psychedelic experience continues to remain the subject of ongoing scientific inquiry.

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.[6]

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.[7]

A study demonstrated that DOI, DMT, LSD, and noribogaine (a metabolite of ibogaine) promote neuritogenesis both in vitro and in vivo.[8]

Subjective effects

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 PsychonautWiki contributors. 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 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.
    • 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.
    • Bodily control enhancement
    • 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.
    • Increased blood pressure[citation needed]
    • Increased heart rate[citation needed]
    • Muscle contractions
    • Muscle spasms
    • 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.
    • Appetite suppression
    • Dehydration
    • Diarrhea
    • Increased perspiration
    • Pupil dilation
    • Teeth grinding
    • Increased salivation
    • 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]

Visual effects
 

Cognitive effects
 

Auditory effects
 

Multi-sensory effects
 

    • 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.

Transpersonal effects
 

Experience reports

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 a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it.
Note: Always conduct independent research and use harm reduction practices if using this substance.

Further information: Research chemicals § Toxicity and harm potential, and Responsible use § Hallucinogens

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 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). 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 harm reduction practices when using this substance.

Overdose

The risk of a DOx overdose is present starting in or past the heavy dose range with sensitive people, or when a DOx is mixed with other substances, particularly stimulants or MAOIs. Non-oral routes also seem to exhibit a higher chance of overdosing, perhaps owing to differences in bioavailability, potency and unpredictability of dosage and effects. The effects of a DOx overdose typically include bizarre, delusional and sometimes violent behavior, amnesia, numbness, confusion and anxiety. The user may not be able to communicate and can be severely agitated. At appropriately high doses, more serious side effects such as psychosis, panic attacks and seizures which in turn further affect a dangerously elevated heart rate, blood pressure and vasoconstriction may occur.[citation needed] Severe vasoconstriction typically develops to its peak several hours into the intoxication and may require medical assistance if blood flow is significantly cut off for extended periods of time.

In the event of an overdose, benzodiazepines or antipsychotics can be administered to mitigate the hyperagitative effects.[citation needed] A powerful vasodilator may also need to be administered to prevent a hypertensive emergency, or in more serious cases, necrosis, organ failure and death from the resulting hypoxia.[citation needed] As a result, emergency medical services should always be sought in the event of a DOx overdose.

Tolerance and addiction potential

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 is 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 all psychedelics, meaning that after the consumption of DOI all psychedelics will have a reduced effect.

Dangerous interactions

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

Legal status

  • Australia: DOI is not listed as a prohibited substance in The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP).[10]
  • 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.[11]
  • Canada: DOI is listed as a Schedule 1 drug as it is an analogue of amphetamine.[12] 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[13] (Narcotics Act, Schedule II) as of December 13, 2014.[14] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[15]
  • Latvia: DOI is a Schedule I controlled substance.[16]
  • 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.[17]
  • 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.[18]
  • Turkey: DOI is a classed as drug and is illegal to possess, produce, supply, or import.[19][20]
  • United Kingdom: DOI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.[21]
  • 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.[22]

See also

External links

Discussion

References

  1. ↑ 1.0 1.1 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. doi:10.1139/v73-210. eISSN 1480-3291. ISSN 0008-4042. OCLC 02248672. 
  2. ↑ 2.0 2.1 Zamberlan, F.; Sanz, C.; Vivot, R. M.; Pallavicini, C.; Erowid, F.; Erowid, E.; Tagliazucchi, E. (2018). "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". Frontiers in Integrative Neuroscience. 12 (54). doi:10.3389/fnint.2018.00054  . eISSN 1662-5145. OCLC 1132048937. PMC 6235949  . PMID 30467466. 
  3. ↑ "LSD Blotter Acid Mimics (Actually Containing 4-Iodo-2,5-dimethoxyamphetamine (DOI) And 4-Chloro-2,5-dimethoxyamphetamine (DOC)) In Lantana, Florida". Microgram Bulletin. Drug Enforcement Administration (DEA). June 2008. OCLC 54464390. Archived from the original on February 4, 2009. 
  4. ↑ Alexander Shulgin; Ann Shulgin (1991). "#67. DOI". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264. 
  5. ↑ Canal, C. E.; Morgan, D. (2012). "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". Drug Testing and Analysis. 4 (7-8): 556–576. doi:10.1002/dta.1333. eISSN 1942-7611. ISSN 1942-7603. OCLC 231680670. PMC 3722587  . PMID 22517680. 
  6. ↑ Yu, B.; Becnel, J.; Zerfaoui, M.; Rohatgi, R.; Boulares, A. H.; Nichols, C. D. (2008). "Serotonin 5-Hydroxytryptamine2A Receptor Activation Suppresses Tumor Necrosis Factor-α-Induced Inflammation with Extraordinary Potency". Journal of Pharmacology and Experimental Therapeutics. 327 (2): 316–323. doi:10.1124/jpet.108.143461. eISSN 1521-0103. ISSN 0022-3565. OCLC 1606914. PMID 18708586. 
  7. ↑ 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. doi:10.1073/pnas.0905884106  . eISSN 1091-6490. ISSN 0027-8424. OCLC 43473694. PMC 2780750  . PMID 19889983. 
  8. ↑ Ly, C.; Greb, A. C.; Cameron, L. P.; Wong, J. M.; Barragan, E. V.; Wilson, P. C.; Burbach, K. F.; Zarandi, S. S.; Sood, A.; Paddy, M. R.; Duim, W. C.; Dennis, M. Y.; McAllister, A. K.; Ori-McKenney, K. M.; Gray, J. A.; Olson, D. E. (2018). "Psychedelics Promote Structural and Functional Neural Plasticity". Cell Reports. 23 (11): 3170–3182. doi:10.1016/j.celrep.2018.05.022  . ISSN 2211-1247. PMC 6082376  . PMID 29898390. 
  9. ↑ 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. ISSN 1556-9039. 
  10. ↑ "Poisons Standard 2013" (PDF). Therapeutic Goods Administration. July 22, 2013. ISBN 978-1-74241-895-7. F2013L01607. 
  11. ↑ "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (Anvisa) [National Sanitary Surveillance Agency]. December 5, 2016. Retrieved January 8, 2020. 
  12. ↑ "Schedule III". Controlled Drugs and Substances Act (CDSA). Isomer Design. Retrieved October 10, 2020. 
  13. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln: Anlage II" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  14. ↑ "Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF). Bundesgesetzblatt Jahrgang 2014 Teil I Nr. 57 (in German). Bundesanzeiger Verlag (published December 12, 2014). December 5, 2014. p. 1999-2002. ISSN 0341-1095. OCLC 231871244. 
  15. ↑ "Gesetz über den Verkehr mit Betäubungsmitteln: § 29" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019. 
  16. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020. 
  17. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 1997:12) om förteckningar över narkotika" (PDF) (in Swedish). Läkemedelsverket [Medical Products Agency ] (published August 30, 2007). August 14, 2007. ISSN 1101-5225. LVFS 2007:10. Archived from the original (PDF) on August 1, 2019. 
  18. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020. 
  19. ↑ "Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742" (in Turkish). Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication] (published January 25, 2014). December 16, 2013. 
  20. ↑ "Kararnamenin Eki: Liste" (PDF). Resmî Gazete, Sayı: 28893 (in Turkish). Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication] (published January 25, 2014). December 16, 2013. 2013/5742. 
  21. ↑ "Psychoactive Substances Act 2016". UK Government. Retrieved January 1, 2020. 
  22. ↑ "The 2015 Florida Statutes - Chapter 893". The Florida Legislature. Retrieved July 18, 2020. 


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