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==Toxicity and harm potential==
==Toxicity and harm potential==
The toxicity and long-term health effects of recreational 2C-I use have not been studied in any scientific context and the exact toxic dosage is unknown. This is because 2C-I is a research chemical with very little history of human usage. Anecdotal evidence from people who have tried 2C-I within the [[psychedelic]] community suggests that there are no negative health effects attributed to simply trying this drug at low to moderate doses or using it very sparingly. However, additional caution is advised since anecdotal evidence suggests that 2C-I seems to cause a higher incidence of side-effects (such as HPPD) while compared to other drugs from the [[2C-x]] family.
The toxicity and long-term health effects of recreational DOI use have not been studied in any scientific context and the exact toxic dosage is unknown. This is because DOI is a research chemical with very little history of human usage. Anecdotal evidence from people who have tried DOI within the [[psychedelic]] community suggests that there are no negative health effects attributed to simply trying this drug at low to moderate doses or using it very sparingly.  


====Tolerance and addiction potential====
====Tolerance and addiction potential====
There is a short period of tolerance after 2C-I use. Using 2C-I two days in a row is likely to lead to a diminished experience the second day. However, this effect is nearly non-existent when spaced 5-7 days apart.
There is a short period of tolerance after DOI use. Using DOI two days in a row is likely to lead to a diminished experience the second day. However, this effect is nearly non-existent when spaced 5-7 days apart.


There does not seem to be any addictive potential.
There does not seem to be any addictive potential.

Revision as of 00:26, 30 October 2015

DOI
Chemical Nomenclature
Common names 2C-I
Substitutive name 2,5-Dimethoxy-4-iodophenethylamine
Systematic name 2-(4-Iodo-2,5-dimethoxyphenyl)ethan-1-amine
Class Membership
Psychoactive class Psychedelic
Chemical class Phenethylamine
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 2 mg
Light 5 - 10 mg
Common 10 - 20 mg
Strong 20 - 30 mg
Heavy 30 mg +
Duration
Total 6 - 10 hours
Onset 15 - 45 minutes
Come up 45 - 90 minutes
Peak 3 - 5 hours
Offset 2 - 3 hours
After effects 6 - 24 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

DOI or 2,5-Dimethoxy-4-iodoamphetamine is a psychedelic drug and a substituted amphetamine. Unlike other substituted amphetamines, however, it is not a stimulant.[2] 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.[2] 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.[3]

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 as a radioligand and indicator of the presence of 5-HT2A serotonin receptors.

Chemistry

General formula of phenethylamine molecule

DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer.

Pharmacology

Main article: Serotonergic psychedelic

DOI's psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Binding Profile of DOI and its isomers
Receptor Ki (racemic DOI)[1] Ki (R-DOI)[1] Ki (S-DOI)[1] Intrinsic activity[2]
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


DOI is a 5-HT2A, 5-HT2B and 5-HT2C receptor agonist.[2]

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.[3]

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.[4]

Subjective effects

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

The physical effects of 2C-I can be broken down into several components which progressively intensify proportional to dosage. These are described below and generally include:

Cognitive effects

Visual effects

Enhancements

Distortions

Geometry

Hallucinatory states

Auditory effects

Multi-sensory effects

Toxicity and harm potential

The toxicity and long-term health effects of recreational DOI use have not been studied in any scientific context and the exact toxic dosage is unknown. This is because DOI is a research chemical with very little history of human usage. Anecdotal evidence from people who have tried DOI within the psychedelic community suggests that there are no negative health effects attributed to simply trying this drug at low to moderate doses or using it very sparingly.

Tolerance and addiction potential

There is a short period of tolerance after DOI use. Using DOI two days in a row is likely to lead to a diminished experience the second day. However, this effect is nearly non-existent when spaced 5-7 days apart.

There does not seem to be any addictive potential.

  • European Union: In December 2003, the European Council issued a binding order compelling all EU member states to ban 2C-I within three months.
  • Denmark: It is a controlled substance.[5]
  • Germany: It is a controlled substance.[5]
  • Greece: It is a controlled substance.[5]
  • Ireland: The drug is a controlled substance.[5]
  • Italy: It is a controlled substance.[5]
  • Netherlands: It is a controlled substance.[5]
  • Poland: It is a controlled substance.[5]
  • Sweden: Sveriges riksdag added 2C-I to Schedule I ("substances, plant materials and fungi which normally do not have medical use") as a narcotic in Sweden as of March 16, 2004. [6]
  • United Kingdom: It is controlled as a Class A substance.[5]
  • U.S.: As of July 9, 2012, 2C-I is a Schedule I substance in the U.S. under the Synthetic Drug Abuse Prevention Act of 2012, making possession, distribution and manufacture illegal.[5]

See also

References

  1. ↑ 1.0 1.1 1.2 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. 
  2. ↑ 2.0 2.1 Canal, CE; Morgan, D (July 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" (PDF). Drug Testing and Analysis. 4 (7-8): 556–576. doi:10.1002/dta.1333. PMC 3722587 Freely accessible. PMID 22517680. 
  3. ↑ Yu, B; Becnel, J; Zerfaoui, M; Rohatgi, R; Boulares, AH; Nichols, CD (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. PMID 18708586. 
  4. ↑ "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. 
  5. ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 5.7 5.8 Erowid.org, Legal Status of 2C-I
  6. ↑ http://www.lakemedelsverket.se/upload/lvfs/LVFS_2004-3.pdf
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