DOx: Difference between revisions

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[[File:DOx.svg|250px|thumbnail|The generic structure for a DOx compound]]

'''DOx''' refers to a class of psychedelic [[amphetamine]]s originally synthesized and documented by [[Alexander Shulgin]] in his investigation of psychoactive [[phenethylamine]]s in the 1970s. Shulgin later published his findings along with other mescaline-derived compounds in his semi-autobiographical book/organic synthesis reference [[PiHKAL]] ("Phenethylamines I Have Known and Loved")<ref>Erowid Online ~~Books~~: ~~"PiHKAL"~~ | https://erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.

'''Substituted dimethoxyamphetamines''' (also known as '''DOx''') refers to a class of psychedelic [[amphetamine]]s originally synthesized and documented by [[Alexander Shulgin]] in his investigation of psychoactive [[phenethylamine]]s in the 1970s. Shulgin later published his findings along with other mescaline-derived compounds in his semi-autobiographical book/organic synthesis reference [[PiHKAL]] ("Phenethylamines I Have Known and Loved")<ref>{{Citation | title=Erowid Online Books : “PIHKAL” - The Chemical Story | url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref>.

The DOx compounds are highly potent, dose-sensitive, and long-lasting substances which are considered considerably more intense and challenging to use than their counterpart [[2C-x]] analogs as well as the [[serotonin|serotonergic]] [[lysergamides]]. The effects of DOx are comprised of strong visuals and an intense body load that is typically accompanied by marked physical and mental stimulation that can persist well past the main duration of its effects (prolonged [[stimulation|residual stimulation]]).

Notably, they are one of the few classes of psychedelic chemicals (the other being the [[25x-NBOMe]] series and the serotonergic [[lysergamides]]) potent enough by weight to be laid onto and distributed on blotter paper, where it is has a history of being sold as a substitute for genuine [[LSD]], being significantly easier to produce. On the street, they are notorious for their distinctly bitter taste as well as their unusually long come-up period (which can take up to 3-4 hours before its main effects even begin to present themselves), which has sometimes led inexperienced LSD users to prematurely conclude that their tabs must be weak or from a "bunk batch" and then take more to try to compensate; this has led to a number of accidental overdoses and unpleasant and overwhelming experiences when the substance's effects finally do take hold.<ref>https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml</ref>

Notably, they are one of the few classes of psychedelic chemicals (the other being the [[25x-NBOMe]] series and the serotonergic [[lysergamides]]) potent enough by weight to be laid onto and distributed on blotter paper, where it is has a history of being sold as a substitute for genuine [[LSD]], being significantly easier to produce. On the street, they are notorious for their distinctly bitter taste as well as their unusually long come-up period (which can take up to 3-4 hours before its main effects even begin to present themselves), which has sometimes led inexperienced LSD users to prematurely conclude that their tabs must be weak or from a "bunk batch" and then take more to try to compensate; this has led to a number of accidental overdoses and unpleasant and overwhelming experiences when the substance's effects finally do take hold.<ref name="PIHKALDOM">{{Citation | title=Erowid Online Books : “PIHKAL” - #68 DOM | url=https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml}}</ref>

==Chemistry==

All derivatives of [[2,5-dimethoxyamphetamine]] have a [[amphetamine]] backbone with two methoxy groups in positions 2 and 5 of the aromatic ring and they further contain different lipophilic substituents in position 4.

== List of DOx compounds ==

===Classic DOx compounds===

{| class="wikitable"

|-

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| DOPR || CH2CH2CH3 || [[File:DOPR.svg|201px]]

|-

| DOiPR || CH(CH3)CH3 || [[File:DOiPR.svg|201px]]

| DOiPR || CH(CH3)2 || [[File:DOiPR.svg|201px]]

|-

| DOBU || CH2CH2CH2CH3 || [[File:DOBU.svg|201px]]

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| Aleph-2 || SCH2CH3 || [[File:Aleph-2.svg|200px]]

|-

| Aleph-4 || SCH(CH3)CH3 || [[File:Aleph-4.svg|200px]]

| Aleph-4 || SCH(CH3)2 || [[File:Aleph-4.svg|200px]]

|-

| Aleph-6 || SC6H5 || [[File:Aleph-6.svg|200px]]

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|}

==~~Health effects~~, potential ~~addiction and tolerance~~==

===Other compounds, derivated from 2,5-dimethoxyamphetamine===

{| class="wikitable"

|-

! scope="col" | '''Compound'''

! scope="col" style="width: 50px;" | '''R3'''

! scope="col" style="width: 100px;" | '''R4'''

! scope="col" style="width: 50px;" | '''R5'''

! scope="col" style="width: 50px;" | '''R6'''

! scope="col" | '''Structure'''

|-

| DOI-2-hemifly || CH2- || I || H || H || [[File:DOI-2-hemifly.svg|200px]]

|-

| DOB-5-hemifly || H || Br || - || CH2- || [[File:DOB-5-hemifly.svg|200px]]

|-

| [[Bromo-DragonFLY]] || CH= || Br || H || CH= || [[File:Bromo-DragonFLY.svg|200px]]

|-

| F-2 || H || CH2- || (CH3)- || H || [[File:F-2.svg|200px]]

|-

| F-22 || H || CH2- || (CH3)2- || H || [[File:F-22.svg|200px]]

|-

|}

==Toxicity and harm potential==

The DOx ~~chemicals~~, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]s) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an excess of serotonin builds up past the body's ability to catabolize it (i.e. "break it down"), which can lead to many physical and cognitive health problems. Also, an oft-observed phenomenon of the DOx chemicals is that they have an extremely long onset time relative to other [[psychedelics]] (which could prompt users to redose early and repeatedly, potentially causing a [[drug overdose]]<ref~~>https://www.erowid.org/library/books_online/pihkal~~/~~pihkal068.shtml</ref~~>).

The DOx compounds, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]s) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an excess of serotonin builds up past the body's ability to catabolize it (i.e. "break it down"), which can lead to many physical and cognitive health problems. Also, an oft-observed phenomenon of the DOx chemicals is that they have an extremely long onset time relative to other [[psychedelics]] (which could prompt users to redose early and repeatedly, potentially causing a [[drug overdose]]<ref name="PIHKALDOM"/>).

==Legal issues==

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*'''United States:''' In the US, some of the DOx chemicals are listed as Schedule I substances and all others under the Federal Analogue Act.

*'''Australia:''' Australia has a blanket ban over all substituted phenethylamines including the entire DOx family.<ref>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</ref>

*'''Switzerland:''' DOM, DOB and DOET are illegal to possess, produce and sell.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>

*'''Switzerland:''' DOM, DOB and DOET are illegal to possess, produce and sell.<ref>{{Citation | year=2017 | title=SR 812.121.11 Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI) | url=http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html}}</ref>

==See also==

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*[[Psychedelics]]

*[[Phenethylamines]]

==External links==

*[https://en.wikipedia.org/wiki/DOx DOx (Wikipedia)]

==References==

[[Category:Chemical class]]

[[Category:Psychedelic]]

[[Category:DOx| ]]

@@ Line 1: / Line 1: @@
 [[File:DOx.svg|250px|thumbnail|The generic structure for a DOx compound]]
-'''DOx''' refers to a class of psychedelic [[amphetamine]]s originally synthesized and documented by [[Alexander Shulgin]] in his investigation of psychoactive [[phenethylamine]]s in the 1970s. Shulgin later published his findings along with other mescaline-derived compounds in his semi-autobiographical book/organic synthesis reference [[PiHKAL]] ("Phenethylamines I Have Known and Loved")<ref>Erowid Online Books: "PiHKAL" | https://erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.
+'''Substituted dimethoxyamphetamines''' (also known as '''DOx''') refers to a class of psychedelic [[amphetamine]]s originally synthesized and documented by [[Alexander Shulgin]] in his investigation of psychoactive [[phenethylamine]]s in the 1970s. Shulgin later published his findings along with other mescaline-derived compounds in his semi-autobiographical book/organic synthesis reference [[PiHKAL]] ("Phenethylamines I Have Known and Loved")<ref>{{Citation | title=Erowid Online Books : “PIHKAL” - The Chemical Story | url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref>.
 The DOx compounds are highly potent, dose-sensitive, and long-lasting substances which are considered considerably more intense and challenging to use than their counterpart [[2C-x]] analogs as well as the [[serotonin|serotonergic]] [[lysergamides]]. The effects of DOx are comprised of strong visuals and an intense body load that is typically accompanied by marked physical and mental stimulation that can persist well past the main duration of its effects (prolonged [[stimulation|residual stimulation]]).
-Notably, they are one of the few classes of psychedelic chemicals (the other being the [[25x-NBOMe]] series and the serotonergic [[lysergamides]]) potent enough by weight to be laid onto and distributed on blotter paper, where it is has a history of being sold as a substitute for genuine [[LSD]], being significantly easier to produce. On the street, they are notorious for their distinctly bitter taste as well as their unusually long come-up period (which can take up to 3-4 hours before its main effects even begin to present themselves), which has sometimes led inexperienced LSD users to prematurely conclude that their tabs must be weak or from a "bunk batch" and then take more to try to compensate; this has led to a number of accidental overdoses and unpleasant and overwhelming experiences when the substance's effects finally do take hold.<ref>https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml</ref>
+Notably, they are one of the few classes of psychedelic chemicals (the other being the [[25x-NBOMe]] series and the serotonergic [[lysergamides]]) potent enough by weight to be laid onto and distributed on blotter paper, where it is has a history of being sold as a substitute for genuine [[LSD]], being significantly easier to produce. On the street, they are notorious for their distinctly bitter taste as well as their unusually long come-up period (which can take up to 3-4 hours before its main effects even begin to present themselves), which has sometimes led inexperienced LSD users to prematurely conclude that their tabs must be weak or from a "bunk batch" and then take more to try to compensate; this has led to a number of accidental overdoses and unpleasant and overwhelming experiences when the substance's effects finally do take hold.<ref name="PIHKALDOM">{{Citation | title=Erowid Online Books : “PIHKAL” - #68 DOM | url=https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml}}</ref>
+==Chemistry==
+{{chemistry}}
+All derivatives of [[2,5-dimethoxyamphetamine]] have a [[amphetamine]] backbone with two methoxy groups in positions 2 and 5 of the aromatic ring and they further contain different lipophilic substituents in position 4.
 == List of DOx compounds ==
+===Classic DOx compounds===
 {| class="wikitable"
 |-
@@ Line 19: / Line 24: @@
 | DOPR || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:DOPR.svg|201px]]
 |-
-| DOiPR || CH(CH<sub>3</sub>)CH<sub>3</sub> || [[File:DOiPR.svg|201px]]
+| DOiPR || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:DOiPR.svg|201px]]
 |-
 | DOBU || CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:DOBU.svg|201px]]
@@ Line 47: / Line 52: @@
 | Aleph-2 || SCH<sub>2</sub>CH<sub>3</sub> || [[File:Aleph-2.svg|200px]]
 |-
-| Aleph-4 || SCH(CH<sub>3</sub>)CH<sub>3</sub> || [[File:Aleph-4.svg|200px]]
+| Aleph-4 || SCH(CH<sub>3</sub>)<sub>2</sub> || [[File:Aleph-4.svg|200px]]
 |-
 | Aleph-6 || SC<sub>6</sub>H<sub>5</sub> || [[File:Aleph-6.svg|200px]]
@@ Line 55: / Line 60: @@
 |}
-==Health effects, potential addiction and tolerance==
+===Other compounds, derivated from 2,5-dimethoxyamphetamine===
+{| class="wikitable"
+|-
+! scope="col" | '''Compound'''
+! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
+! scope="col" style="width: 100px;" | '''R<sub>4</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>5</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
+! scope="col" | '''Structure'''
+|-
+| DOI-2-hemifly || CH<sub>2</sub>- || I || H || H || [[File:DOI-2-hemifly.svg|200px]]
+|-
+| DOB-5-hemifly || H || Br || - || CH<sub>2</sub>- || [[File:DOB-5-hemifly.svg|200px]]
+|-
+| [[Bromo-DragonFLY]] || CH= || Br || H || CH= || [[File:Bromo-DragonFLY.svg|200px]]
+|-
+| F-2 || H || CH<sub>2</sub>- || (CH<sub>3</sub>)- || H || [[File:F-2.svg|200px]]
+|-
+| F-22 || H || CH<sub>2</sub>- || (CH<sub>3</sub>)<sub>2</sub>- || H || [[File:F-22.svg|200px]]
+|-
+|}
+==Toxicity and harm potential==
 {{toxicity}}
-The DOx chemicals, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]s) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an excess of serotonin builds up past the body's ability to catabolize it (i.e. "break it down"), which can lead to many physical and cognitive health problems. Also, an oft-observed phenomenon of the DOx chemicals is that they have an extremely long onset time relative to other [[psychedelics]] (which could prompt users to redose early and repeatedly, potentially causing a [[drug overdose]]<ref>https://www.erowid.org/library/books_online/pihkal/pihkal068.shtml</ref>).
+The DOx compounds, as with many other serotonergic psychedelics, should not be taken in combination with SSRIs (selective [[serotonin]] [[reuptake inhibitor]]s) or [[tricyclic antidepressants]] in general to avoid [[serotonin syndrome]], a potentially life-threatening condition in which an excess of serotonin builds up past the body's ability to catabolize it (i.e. "break it down"), which can lead to many physical and cognitive health problems. Also, an oft-observed phenomenon of the DOx chemicals is that they have an extremely long onset time relative to other [[psychedelics]] (which could prompt users to redose early and repeatedly, potentially causing a [[drug overdose]]<ref name="PIHKALDOM"/>).
 ==Legal issues==
@@ Line 63: / Line 90: @@
 *'''United States:''' In the US, some of the DOx chemicals are listed as Schedule I substances and all others under the Federal Analogue Act.
 *'''Australia:''' Australia has a blanket ban over all substituted phenethylamines including the entire DOx family.<ref>New Psychoactive Substances (National Drug and Alcohol Research Centre 2014) | https://comorbidity.edu.au/sites/default/files/cre/page/New%20Psychoactive%20Substances.pdf</ref>
-*'''Switzerland:''' DOM, DOB and DOET are illegal to possess, produce and sell.<ref>http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html</ref>
+*'''Switzerland:''' DOM, DOB and DOET are illegal to possess, produce and sell.<ref>{{Citation | year=2017 | title=SR 812.121.11 Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI) | url=http://web.archive.org/web/20170329020935/https://www.admin.ch/opc/de/classified-compilation/20101220/index.html}}</ref>
 ==See also==
@@ Line 71: / Line 98: @@
 *[[Psychedelics]]
 *[[Phenethylamines]]
+==External links==
+*[https://en.wikipedia.org/wiki/DOx DOx (Wikipedia)]
 ==References==
 <references />
+[[Category:Chemical class]]
+[[Category:Psychedelic]]
+[[Category:DOx| ]]