25I-NBOMe: Difference between revisions

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==Pharmacology==

25I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT2A receptor]] where it acts as ~~an unusually potent and selective~~ [[Agonist#Agonists|~~partial~~ agonist]].<ref name="Ettrup2011"/> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.

25I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT2A receptor]] where it acts as a Full [[Agonist#Agonists|agonist]].<ref name="Ettrup2011" /> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.

Among psychedelics, this compound is considered to be pharmacologically unique in terms of the high potency, affinity, and selectivity with which it binds to the 5-HT2a receptor.<ref name="Ettrup2011" /> Contrary to popular belief, it is not a "full agonist"{{citation needed}}, although questions have been raised about how the effects it produces differ from other 5-HT2a partial agonists, which include the range of traditional psychedelics.

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The Ki values of the following targets were greater than 500 Ki: 5-HT1A, D3, H2, 5-HT1D, α1A adrenergic, δ opioid, serotonin reuptake transporter, 5-HT5A, 5-HT1B, D2, 5-HT7, D1, 5-HT3, 5-HT1E, D5, muscarinic M1-M5, H3, and the dopamine reuptake transporter.<ref name="high specific">{{cite journal | vauthors=((Nichols, D. E.)), ((Frescas, S. P.)), ((Chemel, B. R.)), ((Rehder, K. S.)), ((Zhong, D.)), ((Lewin, A. H.)) | journal=Bioorganic & Medicinal Chemistry | title=High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand | volume=16 | issue=11 | pages=6116–6123 | date=1 June 2008 | issn=1464-3391 | doi=10.1016/j.bmc.2008.04.050}}</ref>

{| class="wikitable sortable" style="text-align: right; margin-left: 10px;"

|+Ki-values<ref name="Ettrup2011"/><ref name="high specific" />

|+Ki-values<ref name="Ettrup2011" /><ref name="high specific" />

! scope="col" |Receptor||Ki (nM)|| class="unsortable" |±

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==Subjective effects==

{{effects/base

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*'''[[Effect::Pupil dilation]]'''

*'''[[Effect::Headaches]]'''

*'''[[Effect::Seizures]]'''

*'''[[Effect::Seizures]]'''- This effect is far more common in doses exceeding a heavy dose and may manifest as status epilepticus wherein seizures last more than 5 minutes or do not stop without medical intervention

*'''[[Effect::Rhabdomyolysis]]'''

}}

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*'''[[Effect::Time distortion]]'''

*'''[[Effect::Wakefulness]]'''

*'''[[Effect::HPPD]]'''

}}

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25I-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances. The [[LD50|LD50]] has not yet been determined although it is [[Toxicity::potentially fatal at heavy dosages]].<ref name="25Ifatal">{{Citation | title=Erowid 25I-NBOMe (2C-I-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}</ref> [[PsychonautWiki]] advises that due to 25I-NBOMe's extreme potency it should not be insufflated as this method of administration appears to have led to several deaths in the past year.

This substance came to media attention in early 2012 after a cluster of seven non-fatal [[overdose]]s with the drug were reported in or around Richmond, Virginia.<ref name="Kids overdosing on new drug">{{Citation | vauthors=((Geller, L.)) | year=2012 | title=Kids overdosing on new drug | publisher=WWBT NBC12 | url=https://www.nbc12.com/story/16964534/kids-overdosing-on-new-drug}}</ref><ref name="New street drug"> New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012, | http://www.wsfa.com/story/16977573/new-street-drug-causing-concern-among-medics</ref> As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States.<ref>{{Citation | title=New drug N-bomb hits the street, terrifying parents, troubling cops | url=https://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327</ref> In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks, Minnesota fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor.<ref> Breaking Bad: Digital Drug Sales, Analog Drug Deaths. Craig Malisow, Houston Press, March 13, 2013 | http://www.houstonpress.com/2013-03-14/news/motion-research-charles-carlton/</ref>

This substance came to media attention in early 2012 after a cluster of seven non-fatal [[overdose]]s with the drug were reported in or around Richmond, Virginia.<ref name="Kids overdosing on new drug">{{Citation | vauthors=((Geller, L.)) | year=2012 | title=Kids overdosing on new drug | publisher=WWBT NBC12 | url=https://www.nbc12.com/story/16964534/kids-overdosing-on-new-drug}}</ref><ref name="New street drug"> New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012, | http://www.wsfa.com/story/16977573/new-street-drug-causing-concern-among-medics</ref> As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States.<ref><nowiki>{{Citation | title=New drug N-bomb hits the street, terrifying parents, troubling cops | url=</nowiki>https://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327</ref> In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks, Minnesota fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor.<ref> Breaking Bad: Digital Drug Sales, Analog Drug Deaths. Craig Malisow, Houston Press, March 13, 2013 | http://www.houstonpress.com/2013-03-14/news/motion-research-charles-carlton/</ref>

A 21-year-old man from Little Rock, Arkansas died in October 2012 after taking a liquid drop of the drug nasally at a music festival. He was reported to have consumed caffeinated alcoholic beverages for "several hours" beforehand. It is unclear what other drugs he may have consumed, as autopsies usually do not test for the presence of research chemicals.<ref name="21 yr old dies">{{Citation | vauthors=((Martin, N.)) | year=2012 | title=21-year-old dies after one drop of new synthetic drug at Voodoo Fest | publisher=NOLA | url=https://www.nola.com/news/crime_police/article_526a4b28-8e79-5b4c-8310-637c946b616c.html}}</ref>

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In September 2014, the European Council decided that 25I-NBOMe shall be subjected by the Member States to control measures and criminal penalties by October 2, 2015.<ref>{{cite web|url=https://op.europa.eu/o/opportal-service/download-handler?identifier=025bb164-4937-11e4-a0cb-01aa75ed71a1&format=pdfa1a&language=en&productionSystem=cellar&part=|title=Council Implementing Decision on subjecting 25I-NBOMe, AH-7921, MDPV and methoxetamine to control measures|date=September 25, 2014|publication-date=October 1, 2014|work=Official Journal of the European Union|pages=22-26|id=L 287|publisher=Office for Official Publications of the European Communites|oclc=52224955}}</ref>

*'''Australia''': Possession, production and sale is illegal.~~{{citation needed}}~~

*'''Australia''': Possession, production and sale is illegal.<ref>https://web.archive.org/web/20160602092257/https://www.legislation.gov.au/Details/F2015L01534/Html/Text#_Toc420496379</ref>

*'''Austria''': Since June 26, 2019, 25I-NBOMe is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)<ref>https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig</ref>

*'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>

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*'''Japan''': 25I-NBOMe is a narcotic drug in Japan effective November 1st, 2015.<ref>{{Citation | title=新たに４物質を麻薬に指定し、規制の強化を図ります｜報道発表資料｜厚生労働省 | publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)] | url=https://www.mhlw.go.jp/stf/houdou/0000098723.html}}</ref>

*'''Latvia''': 25I-NBOMe is a Schedule I controlled substance.<ref>{{Citation | title=Zaudējis spēku - Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | url=https://likumi.lv/doc.php?id=121086}}</ref>

*'''The Netherlands:''' 25I-NBOMe is classified as a Lijst 1 (List 1) controlled substance under the Opiumwet (Opium Law). <ref>https://wetten.overheid.nl/BWBR0001941/2024-04-16#BijlageI</ref>

*'''New Zealand''': 25I-NBOMe is a Schedule 2 controlled substance in New Zealand.<ref>{{Citation | title=Misuse of Drugs Act 1975 No 116 (as at 07 December 2021), Public Act – New Zealand Legislation | url=https://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html}}</ref>

*'''Norway''': 25I-NBOMe is controlled by the generic scheduling of phenethylamines as of February 14, 2013.<ref name="EMCDDA"></ref>

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*[https://erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml 25I-NBOMe (Erowid Vault)]

*[https://isomerdesign.com/PiHKAL/explore.php?id=5380 25I-NBOMe (Isomer Design)]

*[https://drugs-forum.com/wiki/25I-NBOMe 25I-NBOMe (Drugs-Forum)]

===Discussion===

@@ Line 18: / Line 18: @@
 ==Pharmacology==
 {{Further|Serotonergic psychedelic}}
-I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as an unusually potent and selective [[Agonist#Agonists|partial agonist]].<ref name="Ettrup2011"/> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
+I-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a Full [[Agonist#Agonists|agonist]].<ref name="Ettrup2011" /> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
 Among psychedelics, this compound is considered to be pharmacologically unique in terms of the high potency, affinity, and selectivity with which it binds to the 5-HT2a receptor.<ref name="Ettrup2011" /> Contrary to popular belief, it is not a "full agonist"{{citation needed}}, although questions have been raised about how the effects it produces differ from other 5-HT2a partial agonists, which include the range of traditional psychedelics.
@@ Line 24: / Line 24: @@
 The Ki values of the following targets were greater than 500 Ki: 5-HT1A, D3, H2, 5-HT1D, α1A adrenergic, δ opioid, serotonin reuptake transporter, 5-HT5A, 5-HT1B, D2, 5-HT7, D1, 5-HT3, 5-HT1E, D5, muscarinic M1-M5, H3, and the dopamine reuptake transporter.<ref name="high specific">{{cite journal | vauthors=((Nichols, D. E.)), ((Frescas, S. P.)), ((Chemel, B. R.)), ((Rehder, K. S.)), ((Zhong, D.)), ((Lewin, A. H.)) | journal=Bioorganic & Medicinal Chemistry | title=High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand | volume=16 | issue=11 | pages=6116–6123 | date=1 June 2008 | issn=1464-3391 | doi=10.1016/j.bmc.2008.04.050}}</ref>
 {| class="wikitable sortable" style="text-align: right; margin-left: 10px;"
-|+Ki-values<ref name="Ettrup2011"/><ref name="high specific" />
+|+Ki-values<ref name="Ettrup2011" /><ref name="high specific" />
 ! scope="col" |Receptor||Ki (nM)|| class="unsortable" |±
@@ Line 52: / Line 52: @@
 ==Subjective effects==
 {{Preamble/SubjectiveEffects}}
 {{effects/base
@@ Line 79: / Line 80: @@
 *'''[[Effect::Pupil dilation]]'''
 *'''[[Effect::Headaches]]'''
-*'''[[Effect::Seizures]]'''
+*'''[[Effect::Seizures]]'''- This effect is far more common in doses exceeding a heavy dose and may manifest as status epilepticus wherein seizures last more than 5 minutes or do not stop without medical intervention
+*'''[[Effect::Rhabdomyolysis]]'''
 }}
@@ Line 149: / Line 151: @@
 *'''[[Effect::Time distortion]]'''
 *'''[[Effect::Wakefulness]]'''
+*'''[[Effect::HPPD]]'''
 }}
@@ Line 185: / Line 188: @@
 I-NBOMe is a relatively new substance, and little is known about its pharmacological risks or its interaction with other substances. The [[LD50|LD<sub>50</sub>]] has not yet been determined although it is [[Toxicity::potentially fatal at heavy dosages]].<ref name="25Ifatal">{{Citation | title=Erowid 25I-NBOMe (2C-I-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2ci_nbome/2ci_nbome_death.shtml}}</ref> [[PsychonautWiki]] advises that due to 25I-NBOMe's extreme potency it should not be insufflated as this method of administration appears to have led to several deaths in the past year.
-This substance came to media attention in early 2012 after a cluster of seven non-fatal [[overdose]]s with the drug were reported in or around Richmond, Virginia.<ref name="Kids overdosing on new drug">{{Citation | vauthors=((Geller, L.)) | year=2012 | title=Kids overdosing on new drug | publisher=WWBT NBC12 | url=https://www.nbc12.com/story/16964534/kids-overdosing-on-new-drug}}</ref><ref name="New street drug"> New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012, | http://www.wsfa.com/story/16977573/new-street-drug-causing-concern-among-medics</ref> As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States.<ref>{{Citation | title=New drug N-bomb hits the street, terrifying parents, troubling cops | url=https://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327</ref> In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks, Minnesota fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor.<ref> Breaking Bad: Digital Drug Sales, Analog Drug Deaths. Craig Malisow, Houston Press, March 13, 2013 | http://www.houstonpress.com/2013-03-14/news/motion-research-charles-carlton/</ref>
+This substance came to media attention in early 2012 after a cluster of seven non-fatal [[overdose]]s with the drug were reported in or around Richmond, Virginia.<ref name="Kids overdosing on new drug">{{Citation | vauthors=((Geller, L.)) | year=2012 | title=Kids overdosing on new drug | publisher=WWBT NBC12 | url=https://www.nbc12.com/story/16964534/kids-overdosing-on-new-drug}}</ref><ref name="New street drug"> New street drug causing concern among medics. Vanessa Araiza, WBRC, Feb 28, 2012, | http://www.wsfa.com/story/16977573/new-street-drug-causing-concern-among-medics</ref> As of May 2013, 25I-NBOMe has reportedly led to five overdose deaths in the United States.<ref><nowiki>{{Citation | title=New drug N-bomb hits the street, terrifying parents, troubling cops | url=</nowiki>https://www.nydailynews.com/news/national/new-synthetic-hallucinogen-n-bomb-killing-users-cops-article-1.1336327</ref> In June 2012, two teens in Grand Forks, North Dakota and East Grand Forks, Minnesota fatally overdosed on a substance that was allegedly 25I-NBOMe, resulting in lengthy sentences for two of the parties involved and a Federal indictment against the Texas-based online vendor.<ref> Breaking Bad: Digital Drug Sales, Analog Drug Deaths. Craig Malisow, Houston Press, March 13, 2013 | http://www.houstonpress.com/2013-03-14/news/motion-research-charles-carlton/</ref>
 A 21-year-old man from Little Rock, Arkansas died in October 2012 after taking a liquid drop of the drug nasally at a music festival. He was reported to have consumed caffeinated alcoholic beverages for "several hours" beforehand. It is unclear what other drugs he may have consumed, as autopsies usually do not test for the presence of research chemicals.<ref name="21 yr old dies">{{Citation | vauthors=((Martin, N.)) | year=2012 | title=21-year-old dies after one drop of new synthetic drug at Voodoo Fest | publisher=NOLA | url=https://www.nola.com/news/crime_police/article_526a4b28-8e79-5b4c-8310-637c946b616c.html}}</ref>
@@ Line 213: / Line 216: @@
 In September 2014, the European Council decided that 25I-NBOMe shall be subjected by the Member States to control measures and criminal penalties by October 2, 2015.<ref>{{cite web|url=https://op.europa.eu/o/opportal-service/download-handler?identifier=025bb164-4937-11e4-a0cb-01aa75ed71a1&format=pdfa1a&language=en&productionSystem=cellar&part=|title=Council Implementing Decision on subjecting 25I-NBOMe, AH-7921, MDPV and methoxetamine to control measures|date=September 25, 2014|publication-date=October 1, 2014|work=Official Journal of the European Union|pages=22-26|id=L 287|publisher=Office for Official Publications of the European Communites|oclc=52224955}}</ref>
-*'''Australia''': Possession, production and sale is illegal.{{citation needed}}
+*'''Australia''': Possession, production and sale is illegal.<ref>https://web.archive.org/web/20160602092257/https://www.legislation.gov.au/Details/F2015L01534/Html/Text#_Toc420496379</ref>
 *'''Austria''': Since June 26, 2019, 25I-NBOMe is illegal to possess, produce and sell under the SMG. (Suchtmittelgesetz Österreich)<ref>https://www.ris.bka.gv.at/Dokumente/BgblAuth/BGBLA_2019_II_167/BGBLA_2019_II_167.pdfsig</ref>
 *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7</ref>
@@ Line 226: / Line 229: @@
 *'''Japan''': 25I-NBOMe is a narcotic drug in Japan effective November 1st, 2015.<ref>{{Citation | title=新たに４物質を麻薬に指定し、規制の強化を図ります ｜報道発表資料｜厚生労働省 | publisher=厚生労働省 [Ministry of Health, Labour and Welfare (MHLW)] | url=https://www.mhlw.go.jp/stf/houdou/0000098723.html}}</ref>
 *'''Latvia''': 25I-NBOMe is a Schedule I controlled substance.<ref>{{Citation | title=Zaudējis spēku - Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | url=https://likumi.lv/doc.php?id=121086}}</ref>
+*'''The Netherlands:''' 25I-NBOMe is classified as a Lijst 1 (List 1) controlled substance under the Opiumwet (Opium Law). <ref>https://wetten.overheid.nl/BWBR0001941/2024-04-16#BijlageI</ref>
 *'''New Zealand''': 25I-NBOMe is a Schedule 2 controlled substance in New Zealand.<ref>{{Citation | title=Misuse of Drugs Act 1975 No 116 (as at 07 December 2021), Public Act – New Zealand Legislation | url=https://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html}}</ref>
 *'''Norway''': 25I-NBOMe is controlled by the generic scheduling of phenethylamines as of February 14, 2013.<ref name="EMCDDA"></ref>
@@ Line 252: / Line 256: @@
 *[https://erowid.org/chemicals/2ci_nbome/2ci_nbome.shtml 25I-NBOMe (Erowid Vault)]
 *[https://isomerdesign.com/PiHKAL/explore.php?id=5380 25I-NBOMe (Isomer Design)]
+*[https://drugs-forum.com/wiki/25I-NBOMe 25I-NBOMe (Drugs-Forum)]
 ===Discussion===