DOI

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

2C-I's psychedelic effects are believed to come from its efficacy at the 5-HT_2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.

Pharmacology

Binding Profile of DOI and its isomers

Receptor	Ki (racemic DOI)	Ki (R-DOI)	Ki (S-DOI)	Intrinsic activity
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-HT_2A, 5-HT_2B and 5-HT_2C receptor agonist.

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_2A agonists an entirely new area for development of novel treatments for these conditions.

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.

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 - The "body high" of 2C-I is manifested as one of the most proportionally intense in comparison to almost all of the classical psychedelics. The sensation itself can be described as an intense and slightly uncomfortable energetic pins and needles sensation that constantly 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. Alongside of this, many users commonly report that the "body high" can be particularly uncomfortable and sometimes accompanied by dysphoric aches and urges to shift the position of one's body and prolonged tensing of unusual combinations of muscle groups.
• Euphoria - Feelings of frequent but unpredictable rushes of warm physical euphoria are extremely common and very pleasurable. These move from the top of the head downwards before enveloping one's whole body.
• Stimulation - In terms of its effects on the physical energy levels of the tripper, 2C-I is usually considered to be very energetic and stimulating in a fashion that is quite comparable to that of MDMA although it is encouraged instead of forced.
• Nausea - Mild to extreme nausea is consistently reported when consumed in moderate to high doses and either passes once the tripper has vomited or gradually fades by itself as the peak sets in.
• Bodily control enhancement
• Tactile enhancement
• Temperature regulation loss
• Increased heart rate
• Pupil dilation

Cognitive effects

The head space of 2C-I is described by many as one which is relatively normal in its thought processes even at moderate to high doses. It is often said to lack insight when compared to that of 2C-E, 2C-B and LSD.

The total sum of these cognitive components regardless of the setting generally includes:

• Empathy, love and sociability enhancement - This component is consistently manifested only in the context of social settings in which one is within the company of others. These feelings of sociability, love and empathy are a little weaker and less sharp than those found on substances such as MDMA and 2C-B but still prove strong enough to provide long-lasting therapeutic effects.
• 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

2C-I presents a full and complete array of possible visual enhancements which generally includes:

• Acuity enhancement
• Colour enhancement
• Pattern recognition enhancement

Distortions

2C-I presents a full and complete array of possible visual distortions which generally includes:

• Drifting (melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as simplistic and bland in detail, slow and smooth but sometimes jittery in motion, static in appearance and unrealistic/cartoon-like in style.
• Tracers
• Symmetrical texture repetition
• Colour shifting
• Scenery slicing

Geometry

The visual geometry that is present throughout this trip can be described as more similar in appearance to that of LSD or 2C-B than that of 2C-E, psilocin, or ayahuasca although it is much more bland and less detailed. They can be comprehensively described as unstructured in their organization, algorithmic in geometric style, intricate in complexity, large in size, fast and smooth in motion, colourful in scheme, glossy in colour, both soft and sharp in their edges as well as equally rounded and angular in their corners. They seem high in algorithmic visuals such as fractals and at higher doses are significantly more likely to result in states of level 8A visual geometry over level 8B.

Hallucinatory states

Like LSD, while 2C-I is capable of producing a full range of low and high level hallucinatory states, this is extremely rare and inconsistent at higher levels but common at lower and generally includes the following effects:

• Transformations
• Internal hallucinations (autonomous entities; settings, sceneries, and landscapes; alterations in perspective and scenarios and plots) - Although 2C-I is technically capable of producing hallucinatory states in a fashion that is on par with psilocin or DMT in its vividness and intensity, in comparison, these effects are extremely rare and inconsistent. Whilst traditional psychedelics such as LSA, ayahuasca and mescaline will induce internal hallucinations near consistently at level 5 geometry and above, 2C-I hallucinations will not extend beyond imagery and higher doses will for most simply go straight into level 8A visual geometry. This lack of consistently induced hallucinatory breakthroughs means that, for most, 2C-I is simply not as deep of an experience as certain other psychedelics.

Auditory effects

The auditory effects of 2C-I are common in their occurrence and exhibit a full range of effects which commonly include:

• Enhancements
• Distortions
• Hallucinations

Multi-sensory effects

• Synaesthesia

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.

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 does not seem to be any addictive potential.

Legal issues

• 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.
• Germany: It is a controlled substance.
• Greece: It is a controlled substance.
• Ireland: The drug is a controlled substance.
• Italy: It is a controlled substance.
• Netherlands: It is a controlled substance.
• Poland: It is a controlled substance.
• 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.
• United Kingdom: It is controlled as a Class A substance.
• 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.

See also

• Psychedelics
• Phenethylamines
• DOI (Wikipedia)
• 2C-I (Erowid)