|Summary sheet: DOC|
|Routes of Administration|
4-Chloro-2,5-dimethoxyamphetamine (also known as DOC) is a lesser-known psychedelic substance of the amphetamine class. It is a member of the DOx family of psychedelic amphetamines, which are known for their long duration and mixture of psychedelic and stimulant effects.
DOC was first synthesized by a team at the University of Alberta in 1972. However, its usage in humans was not popularized until the 1991 publication PiHKAL ("Phenethylamines I Have Known And Loved") by Alexander Shulgin. Preceding this, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.
DOC is known as a highly dose-sensitive psychedelic that is often sold in powder form or on blotting paper and known for its long duration (over 12-24 hours), strong visual effects, a unique form of stimulation, and a significant body load.
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 very experienced with hallucinogens. Therefore it is highly advised to approach this unusually dose-sensitive, and long-lasting psychedelic substance with the proper amount of precaution and harm reduction practices if choosing to use it.
History and culture
This History and culture section is a stub.
As a result, it may contain incomplete or wrong information. You can help by expanding it.
DOC was first synthesized by 1972 by Ronald Coutts and Jerry Malicky at the University of Alberta. While human usage was popularized by the 1991 publication of its synthesis and pharmacology in PiHKAL ("Phenethylamines I Have Known And Loved") by Alexander Shulgin, a 1989 forensic analysis of designer amphetamine samples identified DOC in Canadian drug seizures.
DOC or 4-chloro-2,5-dimethoxy-amphetamine, is a molecule of the substituted 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. DOC contains methoxy functional groups OCH3 attached to carbons R2 and R5 and a chlorine atom attached to carbon R4 of the phenyl ring. DOC is the amphetamine analogue of the phenethylamine 2C-C.
DOC is a substituted alpha-methylated phenethylamine, a class of compounds commonly known as amphetamines. The phenethylamine equivalent (lacking the alpha-methyl group) is 2C-C. DOC has a stereocenter and (R)-(−)-DOC is the more active stereoisomer.
DOC acts as a selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated via its actions on the 5-HT2A receptor.
DOC'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.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
- Stimulation - DOC is usually reported 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. The type of stimulation is generally encouraged but can also present some forcefulness to it.
- Spontaneous bodily sensations - The "body high" of DOC is manifested as somewhat 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.
- Physical euphoria - It should be noted that this effect is not as reliably induced as it is with substances like stimulants or entactogens, and can just as easily manifest as physical discomfort without any apparent reason. DOC and other psychedelic amphetamines tend to lean towards physical dysphoria more so than other psychedelics.
- Changes in felt bodily form
- Bodily control enhancement
- Tactile enhancement - Feelings of enhanced tactile sensation are consistently present at low to moderate levels throughout most DOC 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.
- Vasoconstriction - This effect is usually only present at higher dosages, but can be particularly uncomfortable when it manifests, and may persist throughout as well as after the main duration of the experience.
- Increased blood pressure
- Increased heart rate
- Appetite suppression
- Increased perspiration
- Muscle contractions
- Muscle spasms
- Muscle cramps
- Difficulty urinating
- Dry mouth
- Temperature regulation suppression - This effect is more prominent than it is with other psychedelics like LSD.
- Teeth grinding
- Restless legs
- Pupil dilation
- 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.
The visuals of DOC are commonly described as being very simplistic, cartoon-like and linear, when compared to DOB or LSD.
- Drifting (melting, flowing, breathing and morphing) - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and unrealistic/cartoon-like in style.
- Colour shifting
- Depth perception distortions
- Perspective distortions
- Symmetrical texture repetition
- After images
- Brightness alteration
The visual geometry encountered on DOC can be described as more similar in appearance to that of mescaline than that of ayahuasca, psilocybin mushrooms or LSD. It can be comprehensively described through its variations as intricate in complexity, abstract in form, synthetic in feel, structured in organization, brightly lit, multicolored in scheme, glossy in shading, sharp in edges, large in size, fast in speed, smooth in motion, equally rounded and angular in its corners, non-immersive in depth and consistent in intensity. At higher dosages, this geometry is significantly more likely to result in states of level 8B visual geometry over level 8A.
DOC and other substituted amphetamines produce a full range of high-level hallucinatory states in a fashion that is more or less consistent and reproducible than that of many other commonly used psychedelics. These effects include:
- Internal hallucination (autonomous entities; settings, sceneries, and landscapes; perspective hallucinations and scenarios and plots) - In comparison to other psychedelics such as LSD, DOC is extremely high in internal hallucinations when approaching higher dosages. They are more common within dark environments and can be comprehensibly described through its variations as lucid in believability, interactive in style, new experiences in content, autonomous in controllability, geometry-based in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
- External hallucinations - These are often present during the comedown and can include shadow people, among other indescribable beings. These external hallucinations are often lucid, interactive, autonomous, and robust. As sleep deprivation and stimulant psychosis surface, a trip sitter should accompany individuals sensitive to stimulants for the last part of the comedown. The visual effects of psychosis have been reported to blend into the psychedelic visuals around the 16-24 hour mark, sometimes accompanied by auditory hallucinations.
The cognitive effects of DOC are described by many as characterized as prominent 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:
- Anxiety & Paranoia - This effect is not as common at low to moderate doses and is less likely to occur when the basic rules of set and setting are taken into account. It should be noted that this inconsistently induced effect is seemingly more likely to manifest when used with cannabis. This combination should be used with extreme caution if one is not experienced with psychedelics, meaning that the user should adequately pace themselves with a fraction of their usual amount. It is commonly reported that psychedelics can to a certain extent counteract some of the perceived mental cloudiness or intoxicating effects of THC causing the user to in turn use more cannabis than is needed which can often lead to an overwhelmingly anxious and paranoid headspace which can trigger a "bad trip".
- Conceptual thinking
- Thought acceleration
- Thought connectivity
- Empathy, affection, and sociability enhancement - This component is typically manifested only in the context of social settings in which one is within the company of others, and only at lower, non-impairing doses. These feelings of sociability, affection, and empathy tend to be weaker and less consistent than those produced by substances such as MDMA and 2C-B, but can still prove strong enough to provide long-lasting therapeutic effects.
- Cognitive euphoria
- Analysis enhancement - This effect is consistent in its manifestation and outrospection dominant.
- Novelty enhancement
- Immersion enhancement
- Emotion enhancement
- Increased music appreciation
- Increased sense of humor
- Memory suppression
- Ego death - While DOC is technically able to produce states of ego dissolution, it tends to more often than not develop only in extremely high doses, with grave physical and mental side effects being apparent and is often of a terrifying nature.
- Increased libido
- Time distortion
- 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 for those who are already predisposed to synaesthetic states.
Anecdotal reports which describe the effects of this compound within our experience index include:
- Experience: 6mg:DOC - Carpet shop hell
- Experience:20mg DOC (Liquid drops in the mouth) - Inanis Umbra
- Experience:A combination of DOC, 5-MAPB, 5-MeO-DMT, ETH-LAD, Cannabis, Pentedrone
- Experience:Unknown Dose DOC (Insufflated) - Overdosing and Terifying Ego Death
- Experience:Unknown dosage / 1 tab DOC - Psychedelia Turned Into Stimulant Psychosis
Additional experience reports can be found here:
Toxicity and harm potential
The toxicity and long-term health effects of recreational DOC use do not seem to have been studied in any scientific context and the exact toxic dose is unknown.
Anecdotal reports suggest that there are no negative health effects attributed to simply trying DOC by itself at low to moderate doses and 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.
Medical literature reports multiple physical complications associated with the use of DOC. An individual's cause of death was reported as DOC toxicity and confirmed with GC-MS in the Journal of Analytical Toxicology. Seizures have been associated with the use of DOC in another medical journal.
It is strongly recommended that one use harm reduction practices when using this substance.
Tolerance and addiction potential
DOC 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 DOC is 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). DOC presents cross-tolerance with all psychedelics, meaning that after the consumption of DOC all psychedelics will have a reduced effect.
The risk of a DOx overdose is present starting in or past the heavy dose range with sensitive people, or when a DOx is mixed with other substances, particularly stimulants or MAOIs. Non-oral routes also seem to exhibit a higher chance of overdosing, perhaps owing to differences in bioavailability, potency and unpredictability of dosage and effects. The effects of a DOx overdose typically include bizarre, delusional and sometimes violent behavior, amnesia, numbness, confusion and anxiety. The user may not be able to communicate and can be severely agitated. At appropriately high doses, more serious side effects such as psychosis, panic attacks and seizures which in turn further affect a dangerously elevated heart rate, blood pressure and vasoconstriction may occur. Severe vasoconstriction typically develops to its peak several hours into the intoxication and may require medical assistance if blood flow is significantly cut off for extended periods of time.
In the event of an overdose, benzodiazepines or antipsychotics can be administered to mitigate the hyperagitative effects. A powerful vasodilator may also need to be administered to prevent a hypertensive emergency, or in more serious cases, necrosis, organ failure and death from the resulting hypoxia. As a result, emergency medical services should always be sought in the event of a DOx overdose.
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
- Lithium - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
- Cannabis - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of DOC. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
- Stimulants - Stimulants like amphetamine, cocaine or methylphenidate affect many parts of the brain and alter dopaminergic function. This combination can increase the risk of anxiety, paranoia, panic attacks, and thought loops. This interaction may also result in an elevated risk of mania and psychosis.
- Tramadol - Tramadol is well-documented to lower the seizure threshold and psychedelics may act to trigger seizures in susceptible individuals.
- Austria: DOC is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
- Brazil: Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.
- Canada: DOC is Schedule I in Canada, making it illegal to sell, buy, or possess, without a valid legal exemption.
- China: As of October 2015 DOC is a controlled substance in China.
- Denmark: DOC is a Schedule I drug in Denmark.
- Finland: DOC is illegal to possess, produce and sell in Finland.
- Germany: DOC is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of February 1, 1997. It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.
- Israel: The possession, production and sale is illegal.
- Latvia: DOC is a Schedule I controlled substance.
- New Zealand: DOC is a Class C drug in New Zealand.
- Netherlands: Possession, production and sale is illegal.
- Switzerland: DOC can be considered a controlled substance as a defined derivative of a-Methylphenethylamine under Verzeichnis E point 130. It is legal when used for scientific or industrial use.
- Turkey: DOC is a classed as drug and is illegal to possess, produce, supply, or import.
- United Kingdom: DOC is considered a Class A drug as a result of the amphetamine analogue clause of the Misuse of Drugs Act 1971.
- United States: DOC is technically not scheduled in the United States, but could be considered an analogue of DOM or DOB and may therefore be considered a Schedule I drug under the Federal Analogue Act.
- Coutts, R. T.; Malicky, J. L. (1973). "The Synthesis of Some Analogs of the Hallucinogen 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane (DOM)". Canadian Journal of Chemistry. 51 (9): 1402–1409. doi:10.1139/v73-210. eISSN 1480-3291. ISSN 0008-4042. OCLC 02248672.
- Alexander Shulgin; Ann Shulgin (1991). "#64. DOC". PiHKAL: A Chemical Love Story. United States: Transform Press. ISBN 0963009605. OCLC 1166889264.
- Dawson, B. A.; Neville, G. A. (1989). "Identification of Two New "Designer" Amphetamines by NMR Techniques". Canadian Society of Forensic Science Journal. 22 (2): 195–202. doi:10.1080/00085030.198. eISSN 2332-1660. ISSN 0008-5030. OCLC 16515635.
- Barnett, R. Y.; Baker, D. D.; Kelly, N. E.; McGuire, C. E.; Fassette, T. C.; Gorniak, J. M. (2014). "A Fatal Intoxication of 2,5-Dimethoxy-4-Chloroamphetamine: A Case Report". Journal of Analytical Toxicology. 38 (8): 589–591. doi:10.1093/jat/bku087. eISSN 1945-2403. ISSN 0146-4760. OCLC 02942106. PMID 25217551.
- Burish, M. J.; Thoren, K. L.; Madou, M.; Toossi, S.; Shah, M. (2015). "Hallucinogens Causing Seizures? A Case Report of the Synthetic Amphetamine 2,5-Dimethoxy-4-Chloroamphetamine". The Neurohospitalist. 5 (1): 32–34. doi:10.1177/1941874414528939. ISSN 1941-8752. OCLC 969758598. PMC . PMID 25553227.
- Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. doi:10.1007/BF03161089. ISSN 1556-9039.
- "WHO: World Health Organization recommends 12 NPS for scheduling". December 2019. Retrieved October 16, 2020.
- "CND accepts all WHO recommendations on the control of several psychoactive substances from the 42nd ECDD meeting". World Health Organization (WHO). March 18, 2020. Retrieved October 16, 2020.
- "RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016" (in Portuguese). Agência Nacional de Vigilância Sanitária (Anvisa) [National Sanitary Surveillance Agency]. December 5, 2016. Retrieved January 8, 2020.
- "Controlled Drugs and Substances Act (S.C. 1996, c. 19)". Government of Canada. Retrieved September 30, 2020.
- "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). 国家食品药品监督管理总局 [China Food and Drug Administration]. September 27, 2015. Retrieved 1 October 2015.
- "Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "Neunte Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften" (PDF). Bundesgesetzblatt Jahrgang 1997 Teil I Nr. 5 (in German). Bundesanzeiger Verlag (published January 31, 1997). January 28, 1997. p. 65. ISSN 0341-1095.
- "Gesetz über den Verkehr mit Betäubungsmitteln: § 29" (in German). Bundesamt für Justiz [Federal Office of Justice]. Retrieved December 10, 2019.
- "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). VSIA Latvijas Vēstnesis. November 10, 2005. Retrieved January 1, 2020.
- "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Bundeskanzlei [Federal Chancellery of Switzerland]. Retrieved January 1, 2020.
- "Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742" (in Turkish). Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication] (published January 25, 2014). December 16, 2013.
- "Kararnamenin Eki: Liste" (PDF). Resmî Gazete, Sayı: 28893 (in Turkish). Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü [General Directorate of Legislation Development and Publication] (published January 25, 2014). December 16, 2013. 2013/5742.
- "Schedule 2: Part I: Class A Drugs". "Misuse of Drugs Act 1971". UK Government. Retrieved August 20, 2020.