Psychedelic Research Chemicals or RC Chems are new synthetic substances which are structurally similar to the original drug, while being functional analogs. Data on their effects limited due as they’re fairly new and do not have a lot of human consumption history.

Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

Disclaimer: Psychedelic drugs offer some of the most powerful and intense psychological experiences. Additionally these substances are illegal in many places. We understand that even though these substances are illegal, their use occurs frequently. We do not condone breaking of the law. By providing accurate information about these substances, we encourage the user to make responsible decisions and practice harm reduction.

Read the full disclaimer here.

Description

DOI Also known as:

  • 1-(4-Iod-2,5-dimethoxyphenyl)-2-propanamin[German][ACD/IUPAC Name]
  • 1-(4-Iodo-2,5-dimethoxyphenyl)-2-propanamine[ACD/IUPAC Name]
  • 1-(4-Iodo-2,5-diméthoxyphényl)-2-propanamine[French][ACD/IUPAC Name]
  • 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
  • 2,5-Dimethoxy-4-iodoamphetamine
  • 2,5-dimethoxy-4-iodophenylisopropylamine
  • 4-DOI[Formula]
  • 4-iodo-2,5-dimethoxyphenylisopropylamine
  • 4-iodo-2,5-dimethoxyphenylisopropylamine, (±)-isomer
  • 4-iodo-2,5-dimethoxy-α-methylbenzeneethanamine
  • Benzeneethanamine, 4-iodo-2,5-dimethoxy-α-methyl-[ACD/Index Name]
  • (±)2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
  • (±)-2,5-DIMETHOXY-4-IODOAMPHETAMINE
  • [64584-34-5]
  • 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane
  • 1-(2,5-Dimethoxy-4-Iodophenyl)-Propan-2-amine
  • 1-(4-iodo-2,5-dimethoxyphenyl)-2-aminopropane
  • 1-(4-jodo-2,5-dimethoxyphenyl)propan-2-amine[ACD/IUPAC Name]
  • 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine(DOI)
  • 2-(4-Iodo-2,5-dimethoxy-phenyl)-1-methyl-ethylamine[(±) DOI]
  • 4-Iodo-2,5-dimethoxyamphetamine
  • 4-iodo-3-methoxy-N-(1-methoxypropan-2-yl)aniline
  • amphetamine, 2,5-dimethoxy-4-iodo-
  • DOI
  • DOI-P
  • MFCD05662244[MDL number]

A potent, long-acting psychedelic stimulant. Historically, it has rarely been consumed deliberately, but occasionally sold as LSD. However, it has recently found its own little nest in the research chemical community.

Summary

It is a member of the DOx family of psychedelic amphetamines. The synthesis of DOI was first reported in 1972 and its usage in humans was first documented by Alexander Shulgin in the 1991 book PiHKAL ("Phenethylamines I Have Known and Loved"). 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. 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.

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

DOI was first synthesized by a team at the University of Alberta in 1972. ResearchNeuroplasticityOne study demonstrated that DOI, DMT, LSD, and noribogaine (a metabolite of ibogain) promotes neuritogenesis both in vitro and in vivo.

Chemistry

DOI

DOI

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.

Common Name2,5-dimethoxy-4-iodophenylisopropylamine
Systematic name2,5-dimethoxy-4-iodophenylisopropylamine
FormulaC_{11}H_{16}INO_{2}
SMILESCC(Cc1cc(c(cc1OC)I)OC)N
Std. InChiInChI=1S/C11H16INO2/c1-7(13)4-8-5-11(15-3)9(12)6-10(8)14-2/h5-7H,4,13H2,1-3H3
Std. InChiKeyBGMZUEKZENQUJY-UHFFFAOYSA-N
Avg. Mass321.1547 Da
Molecular Weight321.1547
Monoisotopic Mass321.022552 Da
Nominal Mass321
ChemSpider ID1192

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Dose Chart

Oral
Threshold500-750ug.
Light750ug-1mg.
Common1mg-3mg.
Heavy3mg+

Duration Chart

DOI Duration Data
Onset60-90 minutes
Duration12-18 hours
After-effects1-24 hours

Interactions

Caution

  1. Mescaline
  2. NBOMes
  3. 2C-x
  4. 2C-T-x
  5. 5-MeO-xxT
    • The 5-MeO class of tryptamines can be unpredictable in their interactions, particularly increasing the risk of unpleasant physical side effects.
  6. Cannabis
    • Cannabis has an unexpectedly strong and somewhat unpredictable synergy with psychedelics.
  7. MXE
    • As an NMDA antagonist MXE potentiates DOx which can be unpleasantly intense
  8. MDMA
    • The combined stimulating effects of the two can be uncomfortable. Coming down on the MDMA while the DOx is still active can be quite anxiogenic.
  9. Caffeine
    • High doses of caffeine may cause anxiety which is less manageable when tripping, and since both are stimulating it may cause some physical discomfort.
  10. MAOIs
    • MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably

Dangerous

  1. DXM
    • The DOx class as psychedelic stimulants have the potential to mask the effects of DXM and could lead to redosing to an unsafe level. DXM can also potentiate DOx resulting in an unpleasantly intense experience.
  2. PCP
    • Details of this combination are not well understood but PCP generally interacts in an unpredictable manner.
  3. Amphetamines
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of amphetamine can easily lead to thought loops. Coming down from amphetamines while the DOx is still active can be quite anxiogenic.
  4. Cocaine
    • The combined stimulating effects of the two can lead to an uncomfortable body-load, while the focusing effects of cocaine can easily lead to thought loops. Coming down from cocaine while the DOx is still active can be quite anxiogenic
  5. Tramadol
    • Tramadol is well known to lower seizure threshold and psychedelics also cause occasional seizures.

Low Synergy

  1. Alcohol
    • Drinking on stimulants is risky because the sedative effects of the alcohol are reduced, and these are what the body uses to gauge drunkenness. This typically leads to excessive drinking with greatly reduced inhibitions, high risk of liver damage and increased dehydration. They will also allow you to drink past a point where you might normally pass out, increasing the risk.
  2. GHB/GBL
  3. Benzodiazepines
  4. SSRIs

No Synergy

  1. Opioids
    • No unexpected interactions.

High Synergy

  1. Mushrooms
  2. LSD
  3. DMT
  4. Ketamine
    • Ketamine and psychedelics tend to potentiate each other - go slowly.
  5. N2O

Auditory Effects

Psychological Effects

The cognitive effects of DOI are described by many as characterized as extreme mental stimulation combined with a powerful amplification of the user's current mental state. The total sum of these cognitive components regardless of the setting generally includes:

Pharmacological Effects

DOI’s psychedelic effects are believed to come from its efficacy as an agonist at the 5-HT2A, 5-HT2B and 5-HT2C receptors. 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. 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.

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
  • Increased heart rate
  • Muscle contractions
  • Muscle spasms
  • Vasoconstriction - 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.

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.

Subjective Effects

Disclaimer: The effects listed below are cited from the Subjective Effect Index (SEI), which relies on assorted anecdotal reports and the personal experiences of PsychonautWiki contributors. As a result, they should be taken with a healthy amount of skepticism. It is worth noting that these effects will not necessarily occur in a consistent or reliable manner, although higher doses (common+) are more likely to induce the full spectrum of reported effects. Likewise, adverse effects become much more likely on higher doses and may include serious injury or death.

Visual Effects

Enhancements

Distortions

Hallucinatory states

DOI and other psychedelic substituted amphetamines produce a full range of high level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics. This holds particularly true in comparison to other substances within the phenethylamine class. These effects include:

Legal Status

  • Australia: DOI is not listed as a prohibited substance in The Standard for the Uniform Scheduling of Medicines and Poisons (SUSMP).
  • Austria: DOI is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
  • Brazil: DOI is illegal to possess, produce and sell as it is listed on Portaria SVS/MS nº 344.
  • Canada: DOI is listed as a Schedule 1 drug as it is an analogue of amphetamine. 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.
  • Germany: DOI is controlled under Anlage II BtMG (Narcotics Act, Schedule II) as of December 13, 2014. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
  • Latvia: DOI is a Schedule I controlled substance.
  • 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.
  • United Kingdom: DOI is illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.
  • 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.
    • Florida: DOI is a Schedule I controlled substance in the state of Florida.
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    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

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