DOI: Difference between revisions
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==Legal issues== | ==Legal issues== | ||
*''' | *'''Australia''' - The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[11] | ||
*'''Canada''' - Listed as a Schedule 1[12] as it is an analogue of amphetamine.[13] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[14] | |||
*''' | *'''Denmark''' - Illegal since 8 April 2007.[15] | ||
*'''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.[16] | |||
*'''United States''' - DOI is not scheduled in the United States,[17] 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.[citation needed] Scheduling DOI could cause problems for medical researchers.[citation needed] | |||
*''' | *'''Florida''' - DOI is a Schedule I controlled substance in the state of Florida.[18] | ||
*'''Sweden''' | |||
*'''United | |||
*''' | |||
==See also== | ==See also== | ||
Revision as of 00:51, 30 October 2015
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| 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 | |||||||||||||||||||||||||||||||||
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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
DOI has a stereocenter and R-(−)-DOI is the more active stereoisomer.
Pharmacology
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.
| 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:
- Spontaneous tactile sensations
- Euphoria
- Stimulation
- Nausea
- Bodily control enhancement
- Tactile enhancement
- Temperature regulation loss
- Increased heart rate
- Pupil dilation
Cognitive effects
- Empathy, love and sociability enhancement
- Analysis enhancement
- Time distortion
- Novelty enhancement
- Sexual arousal
- Current mind state enhancement
- Immersion enhancement
- Memory suppression
- Ego death
- Unity and interconnectedness
- Wakefulness
Visual effects
Enhancements
Distortions
- Drifting (melting, flowing, breathing and morphing)
- Tracers
- Symmetrical texture repetition
- Colour shifting
- Scenery slicing
Geometry
Hallucinatory states
- Transformations
- Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots)
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.
Legal issues
- Australia - The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP) of Australia does not list DOI as a prohibited substance.[11]
- Canada - Listed as a Schedule 1[12] as it is an analogue of amphetamine.[13] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule 3 to Schedule 1.[14]
- Denmark - Illegal since 8 April 2007.[15]
- 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.[16]
- United States - DOI is not scheduled in the United States,[17] 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.[citation needed] Scheduling DOI could cause problems for medical researchers.[citation needed]
- Florida - DOI is a Schedule I controlled substance in the state of Florida.[18]
See also
References
- ↑ 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.
- ↑ 2.0 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
. PMID 22517680.
- ↑ 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.
- ↑ "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.