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DOI

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DOI
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
Summary sheet: DOI

DOI or 2,5-Dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine. Unlike other substituted amphetamines, however, it is not a traditional stimulant.[1] 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 entheogenic 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 energetic than an LSD trip, with more body load and a different subjective visual experience. The after effects include residual stimulation and difficulty sleeping, which, depending on the dose, may persist for days.[1] 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.[2]

DOI is very well researched in comparison to many drugs, despite being relatively uncommon in terms of its recreational usage. This is because it is often used used in research as a radioligand and indicator of the presence of 5-HT2A serotonin receptors.

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 CH3O- attached to carbons R2 and R5 and a iodine atom attached to carbon R4 of the phenyl ring. DOI is the amphetamine, or alpha-methylated analogue of the phenethylamine 2C-I. [3].

Pharmacology

Main article: 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.[4] However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

DOI and its isomers binding profiles to specific 5HT receptor sets can be seen in the chart below:

Binding Profile of DOI and its isomers
Receptor Ki (racemic DOI)[5] Ki (R-DOI)[5] Ki (S-DOI)[5] Intrinsic activity[4]
5-HT1A 2355 nM 3843 nM ND ND
5-HT1B 1261 nM ND ND ND
5-HT1D 1241.3 nM ND ND ND
5-HT1E 2970 nM ND ND ND
5-HT1F 2125.44 nM ND ND ND
5-HT2A 0.68 nM 0.65 nM 0.65 nM Partial agonist.
5-HT2B 20.03 nM 53.70318 nM 28.183829 nM Partial agonist/full agonist
5-HT2C 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 1000 nM ND ND ND
5-HT5A 1000 nM ND ND ND
5-HT6 >10000 nM ND ND ND

Outside of triggering psychedelia, 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]

Subjective effects

 This subjective effects section is a stub.

As such, it is still in progress and may contain incomplete or wrong information.

You can help by expanding or correcting it.

The effects listed below are based upon the subjective effects index and personal experiences of PsychonautWiki 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.

Physical effects

Cognitive effects

Visual effects

Enhancements

Distortions

Geometry

Hallucinatory states

Auditory effects

Toxicity and harm potential

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 people within the psychedelic 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 or 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.

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 are built almost immediately after ingestion. After that it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). Note that DOI presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of DOI all psychedelics will have a reduced effect.

  • Australia - The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[8]
  • Canada - Listed as a Schedule 1[9] as it is an analogue of amphetamine.[10] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.
  • Denmark - Illegal since 8 April 2007.[11]
  • Sweden - Sveriges riksdag added DOI to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of August 30, 2007, published by Medical Products Agency in their regulation LVFS 2007:10 listed as DOI, 4-jod-2,5-dimetoxi-amfetamin.[12]
  • United States - DOI is not scheduled in the United States, but it is likely that DOI 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.[13]

See also

References

  1. ↑ 1.0 1.1 DOI TiHKAL | http://www.erowid.org/library/books_online/pihkal/pihkal067.shtml
  2. ↑ LSD BLOTTER ACID MIMICS (ACTUALLY CONTAINING 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
  3. ↑ http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=67
  4. ↑ 4.0 4.1 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
  5. ↑ 5.0 5.1 5.2 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
  6. ↑ 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
  7. ↑ "Rapid modulation of spine morphology by the 5-HT2A serotonin receptor through kalirin-7 signaling". Journal of Pharmacology and Experimental Therapeutics. Department of Physiology, Northwestern University Feinberg School of Medicine, Chicago, IL 60611, USA. 17 November 2009. doi:10.1073/pnas.0905884106. PMID 19889983. 
  8. ↑ Therapeutic Goods Administration. Australian Government Department of Health and Ageing | http://www.comlaw.gov.au/Details/F2013L01607/229bdf2e-7014-4379-b751-0b584f55d699
  9. ↑ 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
  10. ↑ 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
  11. ↑ DOC Legal Status by Erowid | http://www.erowid.org/chemicals/doc/doc_law.shtml
  12. ↑ Läkemedelsverkets författningssamling | http://www.lakemedelsverket.se/upload/lvfs/LVFS_2007-10.pdf
  13. ↑ 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
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