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'''4-Bromo-2,5-dimethoxyamphetamine''' (also known as '''Dimethoxybromoamphetamine''', '''Brolamfetamine''', '''Bromo-DMA''', and commonly as '''DOB''') is a [[psychoactive class::psychedelic]] substance of the [[chemical class::amphetamine]] class that produces unusually long-lived [[psychedelic]] effects when [[Routes of administration|administered]]. It is a member of the [[DOx]] family of psychedelic amphetamines.
'''4-Bromo-2,5-dimethoxyamphetamine''' (also known as '''dimethoxybromoamphetamine''', '''brolamfetamine''', '''bromo-DMA''', and commonly as '''DOB''') is a [[psychoactive class::psychedelic]] substance of the [[chemical class::Substituted amphetamine|amphetamine]] class that produces unusually long-lived [[psychedelic]] effects when [[Routes of administration|administered]]. It is a member of the [[DOx]] family of psychedelic amphetamines.
While DOB had first been synthesized in 1967 and briefly tested in 1971, it took until the 1991 publication of the book [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]] to be documented in-depth. The entry for it lists the dose range as 1.0 - 3.0 mg with a duration of 18-30 hours, with varying effects reported.<ref name="pihkalweb">Shulgin, A., & Shulgin, A. (1991). [https://erowid.org/library/books_online/pihkal/pihkal062.shtml Erowid Online Books: "PIHKAL" - #62 DOB]. Retrieved April 14, 2017.</ref>
While DOB had first been synthesized in 1967 and briefly tested in 1971, it took until the 1991 publication of the book [[PiHKAL]] ("Phenethylamines I Have Known And Loved") by [[Alexander Shulgin]] to be documented in-depth.<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal062.shtml|chapter=#62. DOB}}</ref>
Today, DOB is used as a recreational drug and an [[entheogen]]. It is still rarely sold online but is more commonly found in the streets the form of misrepresented [[LSD]] due to its ability to fit onto similar-sized blotter paper.{{citation needed}}
Today, DOB is used as a recreational drug and an [[entheogen]]. It is still rarely sold online but is more commonly found in the streets the form of misrepresented [[LSD]] due to its ability to fit onto similar-sized blotter paper.{{citation needed}}
Despite the many decades that have passed since it was first reported, very little data exists about the pharmacological properties, metabolism, and toxicity of DOB in humans. Along with its sensitive dose-response, unusually long and unpredictable duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with using [[hallucinogens]]. Therefore it is highly advised to approach this unusually powerful and poorly understood [[psychedelic]] substance with the proper amount of precaution and harm reduction practices if choosing to use it.
Very little data exists about the pharmacological properties, metabolism, and toxicity of DOB in humans. Along with its sensitive dose-response, unusually long and unpredictable duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with using [[hallucinogens]]. It is highly advised to use [[harm reduction practices]] if using this substance.
==Chemistry==
==Chemistry==
DOB or 4-Bromo-2,5-dimethoxy-amphetamine is a molecule of the [[amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOB contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a bromine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOB is the amphetamine analogue of the phenethylamine [[2C-B]].<ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62</ref>
DOB or 4-Bromo-2,5-dimethoxy-amphetamine is a molecule of the [[amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOB contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> as well as a bromine atom attached to carbon R<sub>4</sub> of the phenyl ring. DOB is the amphetamine analogue of the phenethylamine [[2C-B]].<ref name="PiHKAL" />
DOB has a stereocenter and ''R''-(–)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other [[phenethylamines]] where the ''R''-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in [[PiHKAL]].
While the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,<ref>{{cite journal | vauthors=((Parrish, J. C.)), ((Braden, M. R.)), ((Gundy, E.)), ((Nichols, D. E.)) | journal=Journal of Neurochemistry | title=Differential phospholipase C activation by phenylalkylamine serotonin 5-HT2A receptor agonists | volume=95 | issue=6 | pages=1575–1584 | date= December 2005 | url=https://onlinelibrary.wiley.com/doi/10.1111/j.1471-4159.2005.03477.x | issn=0022-3042 | doi=10.1111/j.1471-4159.2005.03477.x}}</ref> making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.
==Pharmacology==
==Pharmacology==
{{Further|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
DOB's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. It has been suggested that DOB is a prodrug metabolized in the lungs.<ref>http://www.erowid.org/library/books_online/pihkal/pihkal062.shtml</ref><ref>DOB and Other Possible Prodrugs | http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html</ref>
DOB's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2</sub> receptor]] family as a [[Agonist#Agonists|partial agonist]]. DOB appears to be quite selective for the 5-HT<sub>2B</sub> receptor and is often used in scientific research when studying the 5-HT<sub>2</sub> receptor subfamily. It has been suggested that DOB is a prodrug metabolized in the lungs.<ref name="PiHKAL" /><ref>{{cite web|title=DOB and Other Possible Prodrugs|url=http://www.cognitiveliberty.org/shulgin/blg/2005/05/dob-and-other-possible-prodrugs.html|work=Ask Dr. Shulgin Online|date=May 3, 2005|author=Alexander Shulgin|author-link=Alexander Shulgin|publisher=Center for Cognitive Liberty and Ethics (CCLE)}}</ref> Due to its selectivity, DOB is often used in scientific research when studying the 5-HT<sub>2</sub> receptor subfamily. However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
Furthermore, DOB is an agonist at the Trace-Amine-Associated-Receptor-1 (TAAR1) which contributes to the Amphetamine-Like stimulation.
{| class="wikitable"
Excessively high doses of this hallucinogen may cause diffuse arterial spasm.<ref>{{cite journal | vauthors=((Bowen, J. S.)) | journal=JAMA: The Journal of the American Medical Association | title=Diffuse Vascular Spasm Associated With 4-Bromo-2,5-Dimethoxyamphetamine Ingestion | volume=249 | issue=11 | pages=1477 | date=18 March 1983 | url=http://jama.jamanetwork.com/article.aspx?doi=10.1001/jama.1983.03330350053028 | issn=0098-7484 | doi=10.1001/jama.1983.03330350053028}}</ref> The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.
|-
! Site !! Binding Affinity (nM)
|-
| 5-HT<sub>2A</sub> || 0.6
|-
| 5-HT<sub>2H</sub> || 0.44
|-
| 5-HT<sub>2L</sub> || 59
|-
| 5-HT<sub>2C</sub> || 69
|-
| 5-HT<sub>1A</sub> || 3,700
|-
| 5-HT<sub>1B</sub> || 831
|-
| TAAR1 || Missing Data
|}
However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
==Subjective effects==
==Subjective effects==
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|{{effects/physical|
|{{effects/physical|
*'''[[Effect::Stimulation]]''' - In terms of its effects on the physical energy levels of the user, DOB is usually considered to be extremely stimulating at levels which do not become overwhelming and are encouraged instead of forced. This results in a shakiness and unsteadiness of the hands at high dosages, but encourages the person to move around, run, dance, climb and generally engage in physical activities. The level of stimulation varies between users with some people reporting it to be somewhat similar to [[amphetamine]] in its intensity and others reporting that it is extremely subtle even at higher dosages. In comparison, other more commonly used [[psychedelics]] such as [[psilocin]] are generally sedating and relaxed.
*'''[[Effect::Stimulation]]''' - DOB is usually considered to be extremely stimulating at levels which do not become overwhelming and are encouraged instead of forced. This results in a shakiness and unsteadiness of the hands at high dosages, but encourages the person to move around, run, dance, climb and generally engage in physical activities. The level of stimulation varies between users with some people reporting it to be somewhat similar to [[amphetamine]] in its intensity and others reporting that it is extremely subtle even at higher dosages. In comparison, other more commonly used [[psychedelics]] such as [[psilocin]] are generally sedating and relaxed.
**'''[[Effect::Restless legs]]'''
*'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of DOB 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 static in its position and felt over every square inch of the skin as if it was coming from behind the user's body. Occasionally, however, it manifests itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves.
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of DOB 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 static in its position and felt over every square inch of the skin as if it was coming from behind the user's body. Occasionally, however, it manifests itself in the form of a continuously shifting tingling sensation that travels up and down the body in spontaneous waves.
**'''[[Effect::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. DOB and other psychedelic amphetamines tend to lean towards physical dysphoria more so than other psychedelics.
**'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Changes in felt bodily form]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensation are consistently present at moderate levels throughout most DOB experiences.
*'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensation are consistently present at moderate levels throughout most DOB experiences.
*'''[[Effect::Necrosis]]''' - Serious overdoses have sometimes led to necrosis.{{citation needed}}
*'''[[Effect::Nausea]]''' - Moderate to extreme nausea is typically reported when consumed in moderate to high dosages and either passes once the user has vomited or gradually fades by itself as the peak sets in.
*'''[[Effect::Difficulty urinating]]'''
*'''[[Effect::Nausea]]''' - Mild to extreme nausea is typically reported when consumed in moderate to high dosages and either passes once the user has vomited or gradually fades by itself as the peak sets in.
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Vasoconstriction]]''' - This effect seems to be more liable to occur than most other psychedelics and is reported to be particularly uncomfortable when it does occur.
*'''[[Effect::Vasoconstriction]]'''{{citation needed}} - This effect is reported to be more common than with other psychedelics and can feel prominent and uncomfortable.
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Mouth numbing]]'''
*'''[[Effect::Olfactory hallucinations]]'''
*'''[[Effect::Gustatory hallucinations]]'''
*'''[[Effect::Increased salivation]]'''
*'''[[Effect::Increased salivation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Restless legs]]'''
}}
}}
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====Distortions====
====Distortions====
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting# morphing|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.
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting# morphing|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.
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::Tracers]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Brightness alteration]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Diffraction]]'''
*'''[[Effect::Scenery slicing]]'''
====[[Effect::Geometry]]====
====[[Effect::Geometry]]====
The visual geometry that is present throughout this trip can be described as more similar in appearance to that of [[LSD]], [[25I-NBOMe]] or [[2C-B]] than that of [[ayahuasca]], [[psilocin]] or [[DMT]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, algorithmic in form, synthetic in feel, brightly lit, multicoloured 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. Higher dosages are significantly more likely to result in states of [[Effect::8A Geometry|Level 8A]] visual geometry over [[Level 8B]].
DOB visual geometry can be described as more similar in appearance to that of [[LSD]], [[25I-NBOMe]] or [[2C-B]] than that of [[mescaline]], [[psilocin]] or [[DMT]]. It can be comprehensively described through its [[Visual_effects:_Geometry#Variations|variations]] as intricate in complexity, algorithmic in form, synthetic in feel, brightly lit, multicoloured 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. Higher dosages are significantly more likely to result in states of [[Effect::8A Geometry|Level 8A]] visual geometry over [[Level 8B]].
====Hallucinatory states====
====Hallucinatory states====
DOB is capable of producing a full range of low and high level hallucinatory states in a fashion that is significantly less consistent and reproducible than that of many other commonly used psychedelics. These effects include:
DOB 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 [[psychedelic]]s. These effects include:
*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::External hallucinations]]'''
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'') - In comparison to other [[psychedelic]]s such as [[LSD]], DOB is extremely high in internal hallucinations when approaching higher dosages. They are more common within dark environments and can be comprehensibly described through its [[Internal_hallucinations#Variations|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.
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'') - Although DOB 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, DOB will for most simply go straight into [[Level 8A]] [[geometry]]. This lack of consistently induced hallucinatory breakthroughs means that for most, DOB is not as deep of an experience as certain other [[psychedelics]].
*'''[[Effect:: 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.
}}
}}
|{{effects/cognitive|
|{{effects/cognitive|
The head space of DOB is described by many as one of mental stimulation and a powerful enhancement of a person's current mental state. Many users report that it may not be as deep as other traditional psychedelics such as [[LSD]] or [[psilocin]] and that it is comparatively empty regarding its insightfulness.
The head space of DOB is described by many as one of prominent mental stimulation and a powerful enhancement of a person's current mental state. Many users report that it may not be as deep as other traditional psychedelics such as [[LSD]] or [[psilocin]] and that it is comparatively empty regarding its insightfulness.
**'''[[Effect::Ego death]]''' - While DOB 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.
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Time distortion]]'''
*'''[[Effect::Thought loops]]'''
*'''[[Effect::Thought loops]]'''
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}}
}}
{{effects/transpersonal|
{{effects/transpersonal|
'''Note:''' While transpersonal states have been reported following the use of [[DOB]], it seems to happen in a far less consistent and reproducible fashion than it does for the so-called "classical psychedelics." This can perhaps be attributed to the noticeable physical and stimulating effects that this substance produces, which tends to interfere with the ability for the user to immerse themselves in the experience fully.
Transpersonal states are reported to be less consistent and reproducible than on other psychedelics like [[LSD]] or [[psilocybin mushrooms]]. This can perhaps be attributed to the noticeable physical and stimulating effects that this substance produces, which tends to interfere with the ability for the user to immerse themselves in the experience fully.
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
The toxicity and long-term health effects of recreational DOB use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because DOB is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the community who have tried DOB suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
The toxicity and long-term health effects of recreational DOB use do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because DOB is a [[research chemical]] with very little history of human usage.
Anecdotal reports from those who have tried DOB suggests that there are no negative health effects attributed to simply trying the substance by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance.
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Tolerance to the effects of DOB is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::4-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7-10 days]] to be back at baseline (in the absence of further consumption). DOB presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of DOB all psychedelics will have a reduced effect.
Tolerance to the effects of DOB is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::4-7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7-10 days]] to be back at baseline (in the absence of further consumption). DOB presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of DOB all psychedelics will have a reduced effect.
===Overdose===
{{DOxOD}}
===Dangerous interactions===
===Dangerous interactions===
{{DangerousInteractions}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
Although many substances are safe on their own, they can become dangerous and even life-threatening when combined with other substances. The list below contains some common potentially harmful combinations, but may not include all of them. Certain combinations may be relatively harmless in small doses of each but can still increase the risk of unpredictable injury or death. [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
==Legal status==
Internationally, DOB is a Schedule I drug under the Convention on Psychotropic Substances.<ref>{{cite web|archive-url=http://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf|url=http://www.incb.org/pdf/e/list/green.pdf|archive-date=March 2, 2007|title=List of psychotropic substances under international control (Green List)|edition=23rd|date=August 2003|publisher=International Narcotics Control Board (INCB)}}</ref>
*'''[[Tramadol]]''' - Tramadol lowers the seizure threshold<ref>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. https://doi.org/10.1007/BF03161089</ref> and [[psychedelics]] may act as triggers for seizures, particularly in those who are predisposed to them.{{citation needed}}
*'''Australia''': DOB is listed as a Schedule II substance in Australia.{{citation needed}}
*'''[[Stimulants]]''' - Stimulants affect many parts of the brain. Combined with psychedelics, stimulation can turn into uncontrollable [[anxiety]], [[Panic attacks|panic]], [[thought loops]] and [[paranoia]]. This interaction may cause elevated risk of psychosis.{{citation needed}}
*'''Austria''': DOB is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
*'''[https://en.wikipedia.org/wiki/Lithium_(medication) Lithium]''' - Lithium is often used as treatment for bipolar disorder. It may possibly cause elevated risk of seizures and psychosis due to its [[Glutamate|glutaminergic]] and [[GABA|GABAergic]] effects.{{citation needed}}
*'''Canada''': DOB is listed as a Schedule 1 as it is an analogue of amphetamine.<ref>{{cite web|url=http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=ALL&structure=C|title=Schedule III|work=Controlled Drugs and Substances Act (CDSA)|publisher=Isomer Design|access-date=October 10, 2020}}</ref>
*'''Germany''': DOB is controlled under Anlage I BtMG (''Narcotics Act, Schedule I'')<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> as of September 1, 1984.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl184s1081.pdf|title=Erste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Jahrgang 1984 Teil I Nr. 36|page=1081-1086|publication-date=August 8, 1984|language=de|oclc=231871244|issn=0341-1095|date=August 6, 1984}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref>
*'''Latvia''': DOB is a Schedule I controlled substance.<ref>{{cite web|url=http://likumi.lv/doc.php?id=121086|title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem|publisher=VSIA Latvijas Vēstnesis|access-date=January 1, 2020|publication-date=November 10, 2005|language=lv}}</ref>
*'''The Netherlands''': DOB is a Lijst 1 substance, making it a harddrug.<ref>[https://wetten.overheid.nl/BWBR0001941/2024-04-16#BijlageI]Opiumlijst of The Netherlands</ref>
*'''New Zealand''': DOB is Schedule I (Class A) in New Zealand.{{citation needed}} DOB would also qualify as an analogue under New Zealand's catch-all analogues section in Schedule 3 / Class C of their drug laws which would make [[2C-I]], [[2C-E]], [[DOI]], DOB, ephedrine and pseudoephedrine Schedule 3 compounds in the country.{{citation needed}}
*'''Poland''': DOB is controlled in Poland.<ref>{{cite web|publisher=Sejm Rzeczypospolitej Polskiej [Sejm of the Republic of Poland]|url=http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614+2011%2406%2408&min=1|title=Details Servlet}}{{dead link|date=October 2020}}</ref>
*'''Romania''': DOB is a controlled substance, classified as a ''high-risk drug''.<ref>[https://legislatie.just.ro/Public/DetaliiDocument/23629 Law №143 from 26.07.2000], Annex, Table №1</ref>
*'''Switzerland''': DOB is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
*'''United Kingdom''': DOB is Schedule I/Class A in the U.K., making it illegal to sell, buy, or possess without a license.{{citation needed}}
*'''United States''': DOB is Schedule I in the U.S., making it illegal to sell, buy, gift, produce or possess without a DEA license.{{citation needed}}
==Legality==
==See also==
{{legalStub}}
*'''International:''' DOB is a Schedule I drug under the Convention on Psychotropic Substances.<ref>http://web.archive.org/web/20070302130637/http://www.incb.org/pdf/e/list/green.pdf</ref>
*'''Australia:''' DOB is listed as Schedule II.{{citation needed}}
*'''Austria:''' DOB is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).{{citation needed}}
*'''Canada:''' It is listed as a Schedule 1 as it is an analogue of amphetamine.<ref>http://isomerdesign.com/Cdsa/schedule.php?schedule=3§ion=1&structure=C</ref>
*'''New Zealand:''' DOB is Schedule I (Class A) in New Zealand.{{citation needed}} DOB would also qualify as an analogue under New Zealand's catch-all analogues section in Schedule 3 / Class C of their drug laws which would make [[2C-I]], [[2C-E]], [[DOI]], [[DOB]], [[ephedrine]], and [[pseudoephedrine]] Schedule 3 compounds in the country.
*'''Poland:''' DOB is controlled in Poland.<ref>http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614+2011%2406%2408&min=1</ref>
*'''Switzerland:''' DOB is illegal in Switzerland.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
*'''United Kingdom:''' DOB is Schedule I/Class A in the U.K., making it illegal to sell, buy, or possess without a license.{{citation needed}}
*'''United States:''' DOB is Schedule I in the U.S., making it illegal to sell, buy, gift, produce or possess without a DEA license.{{citation needed}}
*'''Latvia:''' DOB is a Schedule I controlled substance.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem (2,5-Dimetoksifeniletānamīni) | http://likumi.lv/doc.php?id=121086</ref>
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[Research chemical]]
*[[Research chemical]]
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==External links==
==External links==
*[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-bromoamphetamine DOB (Wikipedia)]
*[http://en.wikipedia.org/wiki/2,5-Dimethoxy-4-bromoamphetamine DOB (Wikipedia)]
*[http://www.erowid.org/chemicals/dob/dob.shtml DOB (Erowid Vault)]
*[http://www.erowid.org/chemicals/dob/dob.shtml DOB (Erowid Vault)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62 DOB (PiHKAL / Isomer Design)]
*[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62 DOB (PiHKAL / Isomer Design)]
===Forums===
===Discussion===
*[http://www.bluelight.org/vb/threads/325595-The-Big-amp-Dandy-DOB-Thread DOB (Bluelight)]
*[http://www.bluelight.org/vb/threads/325595-The-Big-amp-Dandy-DOB-Thread The Big & Dandy DOB Thread (Bluelight)]
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
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.
4-Bromo-2,5-dimethoxyamphetamine (also known as dimethoxybromoamphetamine, brolamfetamine, bromo-DMA, and commonly as DOB) is a psychedelic substance of the amphetamine class that produces unusually long-lived psychedelic effects when administered. It is a member of the DOx family of psychedelic amphetamines.
While DOB had first been synthesized in 1967 and briefly tested in 1971, it took until the 1991 publication of the book PiHKAL ("Phenethylamines I Have Known And Loved") by Alexander Shulgin to be documented in-depth.[1]
Today, DOB is used as a recreational drug and an entheogen. It is still rarely sold online but is more commonly found in the streets the form of misrepresented LSD due to its ability to fit onto similar-sized blotter paper.[citation needed]
Very little data exists about the pharmacological properties, metabolism, and toxicity of DOB in humans. Along with its sensitive dose-response, unusually long and unpredictable duration, many reports also suggest that this substance may be overly difficult to use safely for those who are not already very experienced with using hallucinogens. It is highly advised to use harm reduction practices if using this substance.
DOB or 4-Bromo-2,5-dimethoxy-amphetamine is a molecule of the 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. DOB contains methoxy functional groups OCH3 attached to carbons R2 and R5 as well as a bromine atom attached to carbon R4 of the phenyl ring. DOB is the amphetamine analogue of the phenethylamine 2C-B.[1]
DOB has a stereocenter and R-(–)-DOB is the eutomer. This is an important finding as it is suggestive that it is targeting different receptors relative to most other phenethylamines where the R-isomer serves as the distomer. The toxicity of DOB is not fully known, although high doses may cause serious vasoconstriction of the extremities. DOB is one of the most potent compounds in PiHKAL.
While the active dose is similar to that of DOI, another psychedelic amphetamine, DOB has been shown to have a higher efficacy in triggering downstream effects mediated by 5-HT2 receptors,[2] making it likely to be slightly more dangerous than DOI in overdose, due to greater vasoconstrictive action. Omission of the amphetamine related α-methyl leads to 2C-B, a compound that possesses a lower affinity for the 5-HT2A receptor and is a weaker receptor agonist which results in drastically reduced vasoconstriction.
DOB's psychedelic effects are believed to come from its efficacy at the 5-HT2 receptor family as a partial agonist. DOB appears to be quite selective for the 5-HT2B receptor and is often used in scientific research when studying the 5-HT2 receptor subfamily. It has been suggested that DOB is a prodrug metabolized in the lungs.[1][3] Due to its selectivity, DOB is often used in scientific research when studying the 5-HT2 receptor subfamily. However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive.
Excessively high doses of this hallucinogen may cause diffuse arterial spasm.[4] The vasospasm responded readily to intra-arterial and intravenous vasodilators, such as tolazoline.
Subjective effects
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 PsychonautWikicontributors. 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 ☠.
Physical effects
Stimulation - DOB is usually considered to be extremely stimulating at levels which do not become overwhelming and are encouraged instead of forced. This results in a shakiness and unsteadiness of the hands at high dosages, but encourages the person to move around, run, dance, climb and generally engage in physical activities. The level of stimulation varies between users with some people reporting it to be somewhat similar to amphetamine in its intensity and others reporting that it is extremely subtle even at higher dosages. In comparison, other more commonly used psychedelics such as psilocin are generally sedating and relaxed.
Spontaneous bodily sensations - The "body high" of DOB 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 static in its position and felt over every square inch of the skin as if it was coming from behind the user's body. Occasionally, however, it 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. DOB and other psychedelic amphetamines tend to lean towards physical dysphoria more so than other psychedelics.
Nausea - Mild to extreme nausea is typically reported when consumed in moderate to high dosages and either passes once the user has vomited or gradually fades by itself as the peak sets in.
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.
DOB visual geometry can be described as more similar in appearance to that of LSD, 25I-NBOMe or 2C-B than that of mescaline, psilocin or DMT. It can be comprehensively described through its variations as intricate in complexity, algorithmic in form, synthetic in feel, brightly lit, multicoloured 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. Higher dosages are significantly more likely to result in states of Level 8A visual geometry over Level 8B.
Hallucinatory states
DOB 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, DOB 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.
Cognitive effects
The head space of DOB is described by many as one of prominent mental stimulation and a powerful enhancement of a person's current mental state. Many users report that it may not be as deep as other traditional psychedelics such as LSD or psilocin and that it is comparatively empty regarding its insightfulness.
Empathy, affection, and sociability enhancement - This component is inconsistently 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 much weaker and less sharp than those found on substances such as MDMA and 2C-B, but still prove strong enough to provide therapeutic effects.
Ego death - While DOB 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.
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 only to be a prominent part of the experience among those who are already predisposed to synaesthetic states.
Transpersonal states are reported to be less consistent and reproducible than on other psychedelics like LSD or psilocybin mushrooms. This can perhaps be attributed to the noticeable physical and stimulating effects that this substance produces, which tends to interfere with the ability for the user to immerse themselves in the experience fully.
The toxicity and long-term health effects of recreational DOB use do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because DOB is a research chemical with very little history of human usage.
Anecdotal reports from those who have tried DOB suggests that there are no negative health effects attributed to simply trying the substance 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.
DOB is not habit-forming, and the desire to use it can decrease with use. It is most often self-regulating.
Tolerance to the effects of DOB is built almost immediately after ingestion. After that, it takes about 4-7 days for the tolerance to be reduced to half and 7-10 days to be back at baseline (in the absence of further consumption). DOB presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of DOB all psychedelics will have a reduced effect.
Overdose
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.[citation needed] 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.[citation needed] 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.[citation needed] As a result, emergency medical services should always be sought in the event of a DOx overdose.
Dangerous interactions
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.
[[Wikipedia:Lithium_(medication)|DangerousInteraction::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.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of DOB. 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.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[5] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
Legal status
Internationally, DOB is a Schedule I drug under the Convention on Psychotropic Substances.[6]
Australia: DOB is listed as a Schedule II substance in Australia.[citation needed]
Austria: DOB is illegal to possess, produce and sell under the SMG (Suchtmittelgesetz Österreich).[citation needed]
Canada: DOB is listed as a Schedule 1 as it is an analogue of amphetamine.[7]
Germany: DOB is controlled under Anlage I BtMG (Narcotics Act, Schedule I)[8] as of September 1, 1984.[9] It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.[10]
Latvia: DOB is a Schedule I controlled substance.[11]
The Netherlands: DOB is a Lijst 1 substance, making it a harddrug.[12]
New Zealand: DOB is Schedule I (Class A) in New Zealand.[citation needed] DOB would also qualify as an analogue under New Zealand's catch-all analogues section in Schedule 3 / Class C of their drug laws which would make 2C-I, 2C-E, DOI, DOB, ephedrine and pseudoephedrine Schedule 3 compounds in the country.[citation needed]
↑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. ISSN1556-9039.
