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25C-NBOMe: Difference between revisions
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'''25C-NBOMe''' (also known as '''Cimbi-82''', '''NBOMe-2C-C''' and '''2C-C-NBOMe''') is a novel [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. It is a member of the 25x-NBOMe series, a recently discovered group of potent psychedelic compounds derived from the [[2C-x]] family. | '''25C-NBOMe''' (also known as '''Cimbi-82''', '''NBOMe-2C-C''' and '''2C-C-NBOMe''') is a novel [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class. It is a member of the 25x-NBOMe series, a recently discovered group of potent psychedelic compounds derived from the [[2C-x]] family. | ||
The name 25C-NBOMe, which is short-hand for 2C-C-NBOMe, is a derivative of the phenethylamine psychedelic [[2C-C]]. It was discovered in 2003 by Ralf Heim at the Free University of Berlin,<ref name="Ralf Heim PhD. (2010-02-28)"> | The name 25C-NBOMe, which is short-hand for 2C-C-NBOMe, is a derivative of the phenethylamine psychedelic [[2C-C]]. It was discovered in 2003 by Ralf Heim at the Free University of Berlin,<ref name="Ralf Heim PhD. (2010-02-28)">{{cite journal | vauthors=((Heim, R.)) | title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2 -Methoxybenzyl-Partialstruktur: Entwicklung eines neuen Struktur-Wirkungskonzepts | date= 2004 | url=https://refubium.fu-berlin.de/handle/fub188/11995 | doi=10.17169/refubium-16193}}</ref> and subsequently investigated by a team at Purdue University led by [[David E. Nichols|David Nichols]].<ref name="Braden. (2007)">{{cite journal | vauthors=((Braden, M. R.)) | journal=Theses and Dissertations Available from ProQuest | title=Towards a biophysical understanding of hallucinogen action | pages=1–176 | date=1 January 2007 | url=http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 | access-date=8 August 2012}}</ref> It has been studied in its radiolabelled form as a potential ligand for mapping the distribution of serotonin-2A receptors in the brain using positron emission tomography (PET).<ref>{{cite journal | vauthors=((Ettrup, A.)), ((Hansen, M.)), ((Santini, M. A.)), ((Paine, J.)), ((Gillings, N.)), ((Palner, M.)), ((Lehel, S.)), ((Herth, M. M.)), ((Madsen, J.)), ((Kristensen, J.)), ((Begtrup, M.)), ((Knudsen, G. M.)) | journal=European Journal of Nuclear Medicine and Molecular Imaging | title=Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers | volume=38 | issue=4 | pages=681–693 | date= April 2011 | url=http://link.springer.com/10.1007/s00259-010-1686-8 | issn=1619-7070 | doi=10.1007/s00259-010-1686-8}}</ref><ref>{{cite book | vauthors=((Hansen, M.)) | date= 2010 | title=Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain: PhD Thesis | publisher=Faculty of Pharmaceutical Sciences, University of Copenhagen | isbn=9788792719003}}</ref> The first reports of human use appeared in 2010 following its appearance on the online [[research chemical]] market. | ||
[[Subjective effects]] include [[stimulation]], [[geometry|open and closed-eye visuals]], [[time distortion]], [[ | [[Subjective effects]] include [[stimulation]], [[geometry|open and closed-eye visuals]], [[time distortion]], [[euphoria]], and [[ego loss]]. 25C-NBOMe's effects are sometimes compared to those of [[LSD]] or [[DOx]]. However, it is reported to have stronger visual effects and less cognitive and emotional effects like [[ego loss]] and [[introspection]]. Additionally, 25C-NBOMe is reported to be considerably more stimulating than other psychedelics. Serious side effects are more common and include [[nausea]], [[muscle tension]], [[anxiety]], cardiovascular effects, and [[seizures]]. | ||
It is worth noting that members of the [[25x-NBOMe|NBOMe]] series are not [[orally]] active and should be administered [[sublingual|sublingually]] (by holding it into one's mouth and allowing it to absorb over a period of 15 minutes). 25C-NBOMe can also be vaporized and inhaled for more rapid and powerful effects and a shorter duration. However, this route of administration is highly advised against due to the difficulties of measuring and handling substances that are active in the microgram range as it significantly increases the risk of overdose. 25C-NBOMe is also sometimes sold as a counterfeit version of LSD due to its similar effects and ability to be laid onto blotter paper. | It is worth noting that members of the [[25x-NBOMe|NBOMe]] series are not [[orally]] active and should be administered [[sublingual|sublingually]] (by holding it into one's mouth and allowing it to absorb over a period of 15 minutes). 25C-NBOMe can also be vaporized and inhaled for more rapid and powerful effects and a shorter duration. However, this route of administration is highly advised against due to the difficulties of measuring and handling substances that are active in the microgram range as it significantly increases the risk of overdose. 25C-NBOMe is also sometimes sold as a counterfeit version of LSD due to its similar effects and ability to be laid onto blotter paper. | ||
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{{pharmacology}} | {{pharmacology}} | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
25C-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|partial agonist]].<ref>Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | 25C-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] where it acts as a potent [[Agonist#Agonists|partial agonist]].<ref>{{cite journal | vauthors=((Hansen, M.)), ((Phonekeo, K.)), ((Paine, J. S.)), ((Leth-Petersen, S.)), ((Begtrup, M.)), ((Bräuner-Osborne, H.)), ((Kristensen, J. L.)) | journal=ACS chemical neuroscience | title=Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | volume=5 | issue=3 | pages=243–249 | date=19 March 2014 | issn=1948-7193 | doi=10.1021/cn400216u}}</ref> However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive. | ||
In comparison to [[2C-C]], the addition of an NBOMe group to the structure results in a sixteen fold increase in potency, allowing even the most extreme of dosages to fit in liquid form onto tabs and blotter paper, which people often mistake for [[LSD]].<ref>25C-NBOMe--new potent hallucinogenic substance identified on the drug market | In comparison to [[2C-C]], the addition of an NBOMe group to the structure results in a sixteen fold increase in potency, allowing even the most extreme of dosages to fit in liquid form onto tabs and blotter paper, which people often mistake for [[LSD]].<ref>{{cite journal | vauthors=((Zuba, D.)), ((Sekuła, K.)), ((Buczek, A.)) | journal=Forensic Science International | title=25C-NBOMe--new potent hallucinogenic substance identified on the drug market | volume=227 | issue=1–3 | pages=7–14 | date=10 April 2013 | issn=1872-6283 | doi=10.1016/j.forsciint.2012.08.027}}</ref> In comparison to LSD however it is only a third of the potency.<ref>{{Citation | title=Erowid 2C-C-NBOMe Vault : Dose/Dosage | url=https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_dose.shtml}}</ref> | ||
==Subjective effects== | ==Subjective effects== | ||
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{{#ask: [[Category:25C-NBOMe]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:25C-NBOMe]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://www.erowid.org/experiences/subs/exp_25CNBOMe.shtml Erowid Experience Vaults: 25C-NBOMe] | |||
*[https://www.erowid.org/experiences/subs/exp_25CNBOMe.shtml Erowid Experience Vaults: 25C-NBOMe] | |||
==Toxicity and harm potential== | ==Toxicity and harm potential== | ||
{{toxicity}} | {{toxicity}} | ||
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | {{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}} | ||
25C-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 can be [[Toxicity::fatal at heavy dosages]].<ref name=" | 25C-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 can be [[Toxicity::fatal at heavy dosages]].<ref name="25Cfatal">{{Citation | title=Erowid 2C-C-NBOMe (25C-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_death.shtml}}</ref><ref>{{cite journal | vauthors=((Tarpgaard, M.)), ((Mærkedahl, R.)), ((Lauridsen, K. B.)) | journal=Ugeskrift for Laeger | title=[Fatal intoxication with the new designer drug 25C-NBOMe] | volume=177 | issue=35 | pages=V09140523 | date=24 August 2015 | issn=1603-6824}}</ref><ref name="Grautoff2014">{{cite journal | vauthors=((Grautoff, S.)), ((Kähler, J.)) | journal=Medizinische Klinik, Intensivmedizin Und Notfallmedizin | title=[Near fatal intoxication with the novel psychoactive substance 25C-NBOMe] | volume=109 | issue=4 | pages=271–275 | date= May 2014 | issn=2193-6226 | doi=10.1007/s00063-014-0360-5}}</ref> | ||
It is advised that due to 25C-NBOMe's extreme potency it should not be insufflated (snorted) as this method of administration has been attributed to several fatal overdoses due to improper dosing.<ref> | It is advised that due to 25C-NBOMe's extreme potency it should not be insufflated (snorted) as this method of administration has been attributed to several fatal overdoses due to improper dosing.<ref name="25Cfatal">{{Citation | title=Erowid 2C-C-NBOMe (25C-NBOMe) Vault : Fatalities / Deaths | url=https://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_death.shtml}}</ref><ref name="Grautoff2014"/> | ||
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. | ||
===Dependence and abuse potential=== | ===Dependence and abuse potential=== | ||
25C-NBOMe is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating. | 25C-NBOMe is [[Addiction potential::not habit-forming]], and the desire to use it can actually decrease with use. It is most often self-regulating. | ||
Tolerance to the effects of 25C-NBOMe | Tolerance to the effects of 25C-NBOMe is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::7 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::14 days]] to be back at baseline (in the absence of further consumption). 25C-NBOMe presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 25C-NBOMe all psychedelics will have a reduced effect. | ||
===Overdose=== | ===Overdose=== | ||
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==Legal status== | ==Legal status== | ||
*'''Austria''': Since June 26, 2019, 25C-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> | *'''Austria''': Since June 26, 2019, 25C-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> | *'''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> | ||
*'''Canada''': 25C-NBOMe would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>Controlled Drugs and Substances Act | *'''Canada''': 25C-NBOMe would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{Citation | vauthors=((Branch, L. S.)) | year=2022 | title=Consolidated federal laws of Canada, Controlled Drugs and Substances Act | url=https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html}}</ref> | ||
*'''China''': As of October 2015 25C-NBOMe is a controlled substance in China.<ref>关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | http://www.sfda.gov.cn/WS01/CL0056/130753.html</ref> | *'''China''': As of October 2015 25C-NBOMe is a controlled substance in China.<ref>关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | http://www.sfda.gov.cn/WS01/CL0056/130753.html</ref> | ||
*'''Germany''': 25C-NBOMe is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of December 13, 2014.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1576023093735|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</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=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | *'''Germany''': 25C-NBOMe is controlled under Anlage I BtMG (Narcotics Act, Schedule I) as of December 13, 2014.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl114s1999.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl114s1999.pdf%27%5D__1576023093735|title=Achtundzwanzigste Verordnung zur Änderung betäubungsmittelrechtlicher Vorschriften|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Anlage I BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</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=§ 29 BtMG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | ||
*'''Israel''': The NBOMe series of psychoactives became controlled in Israel in May, 2013.<ref>https://www.erowid.org/chemicals/nbome/nbome_law.shtml</ref> | *'''Israel''': The NBOMe series of psychoactives became controlled in Israel in May, 2013.<ref name="ErowidNBOMEVault">{{Citation | title=Erowid NBOMe Series Vault : Legal Status | url=https://www.erowid.org/chemicals/nbome/nbome_law.shtml}}</ref> | ||
*'''Italy''': 25C-NBOMe is a Schedule 1 controlled substance in Italy, meaning it is illegal to possess, distribute, and manufacture.<ref>Tabella 1 Stupefacenti dello Stato Italiano |http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref> | *'''Italy''': 25C-NBOMe is a Schedule 1 controlled substance in Italy, meaning it is illegal to possess, distribute, and manufacture.<ref>Tabella 1 Stupefacenti dello Stato Italiano |http://www.salute.gov.it/imgs/C_17_pagineAree_3729_listaFile_itemName_0_file.pdf</ref> | ||
*'''Latvia''': 25C-NBOMe is a Schedule I controlled substance.<ref>Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | *'''Japan''': 25C-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 | access-date=2 May 2022}}</ref> | ||
*'''New Zealand''': 25C-NBOMe was sold as a designer drug in New Zealand in early 2012, but was withdrawn from sale after a statement by Associate Health Minister Peter Dunne that 25C-NBOMe would be considered to be substantially similar in chemical structure to the illegal hallucinogen DOB, and was therefore a Class C controlled drug analogue.<ref> | *'''Latvia''': 25C-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> | ||
*'''Russia''': Russia became the first country to regulate the NBOME class. The entire NBOMe series of psychoactives became controlled in the Russian Federation starting October, 2011.<ref | *'''New Zealand''': 25C-NBOMe was sold as a designer drug in New Zealand in early 2012, but was withdrawn from sale after a statement by Associate Health Minister Peter Dunne that 25C-NBOMe would be considered to be substantially similar in chemical structure to the illegal hallucinogen DOB, and was therefore a Class C controlled drug analogue.<ref>{{Citation | year=2012 | title=“Legal high” DIME not so legal | url=https://www.sciencemediacentre.co.nz/2012/03/13/legal-high-dime-not-so-legal/}}</ref> | ||
*'''Sweden''': 25C-NBOMe is classed as Schedule I.<ref>Läkemedelsverkets författningssamling | *'''Russia''': Russia became the first country to regulate the NBOME class. The entire NBOMe series of psychoactives became controlled in the Russian Federation starting October, 2011.<ref name="ErowidNBOMEVault" /><ref>Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва | http://www.rg.ru/2011/10/19/narko-dok.html</ref> | ||
*'''United Kingdom''': 25C-NBOMe is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref> | *'''Sweden''': 25C-NBOMe is classed as Schedule I.<ref>{{Citation | title=Läkemedelsverkets författningssamling | url=https://www.lakemedelsverket.se/sv/lagar-och-regler/foreskrifter}}</ref> | ||
*'''Switzerland''': 25C-NBOMe 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> | |||
*'''Turkey:''' 25C-NBOMe is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">{{Citation | title=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü | url=https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm}}</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf}}</ref> | |||
*'''United Kingdom''': 25C-NBOMe is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause.<ref>{{Citation | title=The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014 | url=https://www.legislation.gov.uk/uksi/2014/1106/made}}</ref> | |||
*'''United States''': Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years with the possibility of an additional year. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.<ref>DEA proposed rules | http://www.gpo.gov/fdsys/pkg/FR-2013-10-10/pdf/2013-24432.pdf</ref> | *'''United States''': Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years with the possibility of an additional year. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.<ref>DEA proposed rules | http://www.gpo.gov/fdsys/pkg/FR-2013-10-10/pdf/2013-24432.pdf</ref> | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Psychedelics]] | *[[Psychedelics]] | ||
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==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/25C-NBOMe 25C-NBOMe (Wikipedia)] | *[https://en.wikipedia.org/wiki/25C-NBOMe 25C-NBOMe (Wikipedia)] | ||
*[https://erowid.org/chemicals/2cc_nbome/2cc_nbome.shtml 25C-NBOMe (Erowid Vault)] | *[https://erowid.org/chemicals/2cc_nbome/2cc_nbome.shtml 25C-NBOMe (Erowid Vault)] | ||
*[https://isomerdesign.com/PiHKAL/explore.php?id=343 25C-NBOMe (Isomer Design)] | *[https://isomerdesign.com/PiHKAL/explore.php?id=343 25C-NBOMe (Isomer Design)] | ||
*[https://drugs-forum.com/wiki/25C-NBOMe 25C-NBOMe (Drugs-Forum)] | |||
===Discussion=== | ===Discussion=== | ||
*[http://disregardeverythingisay.com/post/60874119182/25c-nbome-broken-down-and-described 25C-NBOMe, broken down and described (Disregard Everything I Say)] | *[http://disregardeverythingisay.com/post/60874119182/25c-nbome-broken-down-and-described 25C-NBOMe, broken down and described (Disregard Everything I Say)] | ||
==References== | ==References== | ||
{{reflist|2}} | {{reflist|2}} | ||
[[Category:Psychoactive substance]] | [[Category:Psychoactive substance]] | ||
[[Category:Psychedelic]] | |||
[[Category:25x-NBOMe]] | |||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
{{#set:Featured=true}} | |||