25x-NBOMe: Difference between revisions

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{{headerpanel|{{Warning/25x-NBOMe}}}}

[[File:25x-NBOMe.~~png~~|301px|thumbnail|The general structure for a 25x-NBOMe compound]]

[[File:25x-NBOMe.svg|301px|thumbnail|The general structure for a 25x-NBOMe compound]]

'''25x-NBOMe''' is the general form of the NBOMe series of psychedelic [[phenethylamines]]. The series ~~has~~ nearly no history of human use ~~prior to~~ 2010 when some of the first compounds became available for purchase from online [[research chemical]] vendors.

'''25x-NBOMe''' is the general form of the NBOMe series of psychedelic [[phenethylamines]]. The series had nearly no history of human use before 2010 when some of the first compounds became available for purchase from online [[research chemical]] vendors.

~~It is~~ often ~~sold~~ as [[LSD]], ~~but one key~~ difference between 25x-~~NBOMe and [[LSD]] is that~~ NBOMe is only active when taken through a sublingual or insufflated route. This means that ~~in order~~ to get the full effects, 25x-NBOMe blotter paper must be lightly chewed on for 20+ minutes and never immediately swallowed. ~~Insufflation~~, ~~however~~, is not recommended; reports of people suffering dangerous and often fatal overdoses ~~due to this route of administration~~ have ~~been surfacing~~.

While members of this series are often misrepresented as [[LSD]], a fundamental difference between them is that 25x-NBOMe is only active when taken through a sublingual or insufflated route. This means that to get the full effects, 25x-NBOMe blotter paper must be lightly chewed on for 20+ minutes and never immediately swallowed.

25x-NBOMe blotters cause numbness of the tongue and have a distinct taste that is often described as "strongly bitter", "metallic", or "chemical like". This is unlike [[LSD]] blotters, which will not cause numbness of the tongue and may be tasteless or have a slight flavor depending on the amount of ink on the blotter and the composition of the blotter paper.

Although these differences can be helpful in identifying an unwanted compound on a blotter, it is recommended that more reliable methods of identification be used, such as the use of [[Responsible drug use|testing reagents]] like the Ehrlich reagent.

Insufflation of these substances are highly discouraged due to numerous reports of people suffering dangerous and often fatal overdoses that have surfaced over the years.{{citation needed}}

==Chemistry==

In a comparison of 25x-NBOMe and [[2C-x]] chemicals, each 25x-NBOMe molecule is a serotonergic N-benzyl derivative of the corresponding [[2C-x]] molecule. This change in structure results in an increase in potency. It differs from the ~~corresponding~~ 2C-x structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. The addition of this BOMe group also causes most of the compounds to have relatively the same duration, regardless of how long the 2C-x counterpart lasts.

In a comparison of 25x-NBOMe and [[2C-x]] chemicals, each 25x-NBOMe molecule is a serotonergic N-benzyl derivative of the corresponding [[2C-x]] molecule. This change in structure results in an increase in potency. It differs from the related 2C-x structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. The addition of this BOMe group also causes most of the compounds to have relatively the same duration, regardless of how long the 2C-x counterpart lasts.

~~==Examples==~~

==List of 25x-NBOMe compounds==

==List of 25x-~~NBOH~~ compounds==

{| class="wikitable"

|-

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

|-

| [[25B-NBOMe]] || Br || [[File:~~25b~~-NBOMe.~~png~~|200px]]

| [[25B-NBOMe]] || Br || [[File:25B-NBOMe.svg|200px]]

|-

| [[25C-NBOMe]] || Cl || [[File:~~25c~~-NBOMe.~~png~~|200px]]

| [[25C-NBOMe]] || Cl || [[File:25C-NBOMe.svg|200px]]

|-

| [[25D-NBOMe]] || CH3 || [[File:25D-NBOMe.~~png~~|200px]]

| [[25D-NBOMe]] || CH3 || [[File:25D-NBOMe.svg|200px]]

|-

| [[25I-NBOMe]] || I || [[File:25I-NBOMe.~~png~~|200px]]

| [[25I-NBOMe]] || I || [[File:25I-NBOMe.svg|200px]]

|-

| [[25N-NBOMe]] || NO2 || [[File:25N-NBOMe.~~png~~|200px]]

| [[25N-NBOMe]] || NO2 || [[File:25N-NBOMe.svg|200px]]

|-

| ~~[[25P~~-NBOMe]] || CH2CH2~~CH3~~ || [[File:~~25P~~-NBOMe.~~png~~|200px]]

| 25iP-NBOMe || CH(CH3)2 || [[File:25iP-NBOMe.svg|200px]]

|-

|}

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

==Toxicity and harm potential==

~~The~~ 25x-NBOMe ~~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 abundance of serotonin is built up the body, causing many physical and cognitive health problems~~.

===Tolerance and addiction potential===

Members of the 25x-NBOMe series are [[Addiction potential::not habit-forming]] and the desire to use them can actually decrease with use. They are thought to be most often self-regulating.

==Legal ~~issues~~==

Tolerance to the effects of any member of the 25x-NBOMe series is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::1 week]] for the tolerance to be reduced to half and [[Time to zero tolerance::2 weeks]] to be back to baseline (in the absence of further consumption). Members of the 25x-NBOMe series present cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of any member of the 25x-NBOMe series all psychedelics will have a reduced effect.

*'''~~USA~~:''' In the US, some of the 25x-NBOMe chemicals are listed as Schedule I substances and all ~~analogs~~ under the ~~Federal Analog~~ Act.

===Overdose===

===Dangerous interactions===

====[[Serotonin syndrome]] risk====

==Legal status==

*'''Austria:''' The 25x-NBOMe family is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}

*'''Poland:''' The 25x-NBOMe family is controlled by Group I-P in "Act of 29 July 2005 on preventing drug addictions" (Ustawa z dnia 29 lipca 2005 o przeciwdziałaniu narkomanii).{{citation needed}}

*'''United States:''' In the US, some of the 25x-NBOMe chemicals are listed as Schedule I substances and others may be considered analogues under the Federal Analogue Act.{{citation needed}}

*'''United Kingdom:''' The majority of synthesised 25x-NBOMe substances are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref>United Kingdom. (2014). Misuse of Drugs Act 1971 (S.I. 2014/1106). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/2014/1106/made</ref> Any compounds not covered by the clause are illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>

==See also==

*[[Responsible use]]

*[[Psychedelics]]

*[[Phenethylamines]]

*[[25x-NBOH]]

*[[2C-x]]

*[[DOx]]

*[[25x-NBOH]]

*[[Psychedelics]]

*[[Phenethylamines]]

==External links==

*[https://en.wikipedia.org/wiki/25-NB 25-NB (Wikipedia)]

*[https://erowid.org/chemicals/nbome/nbome.shtml NBOMe Series (Erowid Vault)]

==Literature==

*Hansen, M., Phonekeo, K., Paine, J. S., Leth-Petersen, S., Begtrup, M., Bräuner-Osborne, H., & Kristensen, J. L. (2014). Synthesis and structure–activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience, 5(3), 243-249. https://doi.org/10.1021/cn400216u

* Heim, Ralf (2004). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur". Freie Universität Berlin. Retrieved 27 June 2015.

* Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. PMC 3963123 Freely accessible. PMID 24397362. https://doi.org/10.1021/cn400216u

* Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. PMID 21174090. https://doi.org/10.1007/s00259-010-1686-8

==References==

[[Category:Chemical class]]

[[Category:25x-NBOMe|*]]

@@ Line 1: / Line 1: @@
-{{Warning/25x-NBOMe}}
+{{headerpanel|{{Warning/25x-NBOMe}}}}
-[[File:25x-NBOMe.png|301px|thumbnail|The general structure for a 25x-NBOMe compound]]
+[[File:25x-NBOMe.svg|301px|thumbnail|The general structure for a 25x-NBOMe compound]]
-'''25x-NBOMe''' is the general form of the NBOMe series of psychedelic [[phenethylamines]]. The series has nearly no history of human use prior to 2010 when some of the first compounds became available for purchase from online [[research chemical]] vendors.
+'''25x-NBOMe''' is the general form of the NBOMe series of psychedelic [[phenethylamines]]. The series had nearly no history of human use before 2010 when some of the first compounds became available for purchase from online [[research chemical]] vendors.
-It is often sold as [[LSD]], but one key difference between 25x-NBOMe and [[LSD]] is that NBOMe is only active when taken through a sublingual or insufflated route. This means that in order to get the full effects, 25x-NBOMe blotter paper must be lightly chewed on for 20+ minutes and never immediately swallowed. Insufflation, however, is not recommended; reports of people suffering dangerous and often fatal overdoses due to this route of administration have been surfacing.
+While members of this series are often misrepresented as [[LSD]], a fundamental difference between them is that 25x-NBOMe is only active when taken through a sublingual or insufflated route. This means that to get the full effects, 25x-NBOMe blotter paper must be lightly chewed on for 20+ minutes and never immediately swallowed.
+x-NBOMe blotters cause numbness of the tongue and have a distinct taste that is often described as "strongly bitter", "metallic", or "chemical like". This is unlike [[LSD]] blotters, which will not cause numbness of the tongue and may be tasteless or have a slight flavor depending on the amount of ink on the blotter and the composition of the blotter paper.
+Although these differences can be helpful in identifying an unwanted compound on a blotter, it is recommended that more reliable methods of identification be used, such as the use of [[Responsible drug use|testing reagents]] like the Ehrlich reagent.
+Insufflation of these substances are highly discouraged due to numerous reports of people suffering dangerous and often fatal overdoses that have surfaced over the years.{{citation needed}}
 ==Chemistry==
-In a comparison of 25x-NBOMe and [[2C-x]] chemicals, each 25x-NBOMe molecule is a serotonergic N-benzyl derivative of the corresponding [[2C-x]] molecule. This change in structure results in an increase in potency. It differs from the corresponding 2C-x structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. The addition of this BOMe group also causes most of the compounds to have relatively the same duration, regardless of how long the 2C-x counterpart lasts.
+In a comparison of 25x-NBOMe and [[2C-x]] chemicals, each 25x-NBOMe molecule is a serotonergic N-benzyl derivative of the corresponding [[2C-x]] molecule. This change in structure results in an increase in potency. It differs from the related 2C-x structurally through a substitution on the amine (NH2) with a 2-methoxybenzyl (BOMe) group. The addition of this BOMe group also causes most of the compounds to have relatively the same duration, regardless of how long the 2C-x counterpart lasts.
-==Examples==
+==List of 25x-NBOMe compounds==
-==List of 25x-NBOH compounds==
 {| class="wikitable"
 |-
@@ Line 18: / Line 22: @@
 ! scope="col" | '''Structure'''
 |-
-| [[25B-NBOMe]] || Br || [[File:25b-NBOMe.png|200px]]
+| [[25B-NBOMe]] || Br || [[File:25B-NBOMe.svg|200px]]
 |-
-| [[25C-NBOMe]] || Cl || [[File:25c-NBOMe.png|200px]]
+| [[25C-NBOMe]] || Cl || [[File:25C-NBOMe.svg|200px]]
 |-
-| [[25D-NBOMe]] || CH<sub>3</sub> || [[File:25D-NBOMe.png|200px]]
+| [[25D-NBOMe]] || CH<sub>3</sub> || [[File:25D-NBOMe.svg|200px]]
 |-
-| [[25I-NBOMe]] || I || [[File:25I-NBOMe.png|200px]]
+| [[25I-NBOMe]] || I || [[File:25I-NBOMe.svg|200px]]
 |-
-| [[25N-NBOMe]] || NO<sub>2</sub> || [[File:25N-NBOMe.png|200px]]
+| [[25N-NBOMe]] || NO<sub>2</sub> || [[File:25N-NBOMe.svg|200px]]
 |-
-| [[25P-NBOMe]] || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || [[File:25P-NBOMe.png|200px]]
+| 25iP-NBOMe || CH(CH<sub>3</sub>)<sub>2</sub> || [[File:25iP-NBOMe.svg|200px]]
 |-
 |}
-==Health effects, potential addiction and tolerance==
+==Toxicity and harm potential==
-The 25x-NBOMe 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 abundance of serotonin is built up the body, causing many physical and cognitive health problems.
+{{toxicity}}
+===Tolerance and addiction potential===
+Members of the 25x-NBOMe series are [[Addiction potential::not habit-forming]] and the desire to use them can actually decrease with use. They are thought to be most often self-regulating.
-==Legal issues==
+Tolerance to the effects of any member of the 25x-NBOMe series is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::1 week]] for the tolerance to be reduced to half and [[Time to zero tolerance::2 weeks]] to be back to baseline (in the absence of further consumption). Members of the 25x-NBOMe series present cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of any member of the 25x-NBOMe series all psychedelics will have a reduced effect.
-*'''USA:''' In the US, some of the 25x-NBOMe chemicals are listed as Schedule I substances and all analogs under the Federal Analog Act.
+===Overdose===
+{{NBOMeOD}}
+===Dangerous interactions===
+{{DangerousInteractions/Intro}}
+{{DangerousInteractions/NBOMe}}
+====[[Serotonin syndrome]] risk====
+{{DangerousInteractions/SerotoninSyndrome}}
+==Legal status==
+{{legalStub}}
+*'''Austria:'''	The 25x-NBOMe family is illegal to possess, produce and sell under the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}}
+*'''Poland:''' The 25x-NBOMe family is controlled by Group I-P in "Act of 29 July 2005 on preventing drug addictions" (Ustawa z dnia 29 lipca 2005 o przeciwdziałaniu narkomanii).{{citation needed}}
+*'''United States:''' In the US, some of the 25x-NBOMe chemicals are listed as Schedule I substances and others may be considered analogues under the Federal Analogue Act.{{citation needed}}
+*'''United Kingdom:''' The majority of synthesised 25x-NBOMe substances are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref>United Kingdom. (2014). Misuse of Drugs Act 1971 (S.I. 2014/1106). London: The Stationery Office Limited. Retrieved July 5, 2017, from http://www.legislation.gov.uk/uksi/2014/1106/made</ref> Any compounds not covered by the clause are illegal to produce, supply, or import under the Psychoactive Substance Act, which came into effect on May 26th, 2016.<ref>Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
 ==See also==
 *[[Responsible use]]
+*[[Psychedelics]]
+*[[Phenethylamines]]
+*[[25x-NBOH]]
 *[[2C-x]]
 *[[DOx]]
-*[[25x-NBOH]]
-*[[Psychedelics]]
-*[[Phenethylamines]]
+==External links==
+*[https://en.wikipedia.org/wiki/25-NB 25-NB (Wikipedia)]
+*[https://erowid.org/chemicals/nbome/nbome.shtml NBOMe Series (Erowid Vault)]
+==Literature==
+*Hansen, M., Phonekeo, K., Paine, J. S., Leth-Petersen, S., Begtrup, M., Bräuner-Osborne, H., & Kristensen, J. L. (2014). Synthesis and structure–activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists. ACS Chemical Neuroscience, 5(3), 243-249. https://doi.org/10.1021/cn400216u
+* Heim, Ralf (2004). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur". Freie Universität Berlin. Retrieved 27 June 2015.
+* Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. PMC 3963123 Freely accessible. PMID 24397362. https://doi.org/10.1021/cn400216u
+*  Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–693. PMID 21174090. https://doi.org/10.1007/s00259-010-1686-8
 ==References==
 <references />
+[[Category:Chemical class]]
+[[Category:25x-NBOMe|*]]