25C-NBOMe: Difference between revisions

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.

25C-NBOMe has efficacy at the [[serotonin#The 5-HT system|5-HT_2A 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>{{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>

 

*[https://www.erowid.org/experiences/subs/exp_25CNBOMe.shtml Erowid Experience Vaults: 25C-NBOMe]

25C-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 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 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"/>

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 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.

*'''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>

*'''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>

*'''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>

*'''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>

*'''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>

*'''Sweden''': 25C-NBOMe is classed as Schedule I.<ref>{{Citation | title=Läkemedelsverkets författningssamling | url=https://www.lakemedelsverket.se/sv/lagar-och-regler/foreskrifter}}</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>