25C-NBOMe: Difference between revisions

{{Short description|Psychedelic drug}}

{{cs1 config|name-list-style=vanc}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451565314

| IUPAC_name = 2-(4-Chloro-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethan-1-amine

| image = 2C-C-NBOMe-skeletal.svg

| image2 = 2C-C-NBOMe-spacefill.png

| width = 200px

| width2 = 200px

| tradename =

| legal_status =

| legal_BR = F2

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_DE = Anlage I

| legal_US =Schedule I

| legal_UK = Class A

| legal_UN = P I

| legal_UN_comment = <ref>{{Cite web |title=Substance Details 25C-NBOMe |url=https://www.unodc.org/LSS/Substance/Details/be41b648-e8e7-4a5b-bec3-51af6c128a9b |access-date=2024-01-23}}</ref>

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 1227608-02-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9FGW3C260N

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C22720

| C=18 | H=22 | Cl=1 | N=1 | O=3

[[File:2C-C-NBOMe.gif|200px|thumb|3D-animation of a 25C-NBOMe molecule]]

[[File:25C-NBOMe blotter.jpg|200px|thumb|Blotter paper containing 25C-NBOMe]]

{{commonscat}}

'''25C-NBOMe''' ('''NBOMe-2C-C''', '''2C-C-NBOMe''', '''Cimbi-82''') is a [[psychedelic drug]] and derivative of the psychedelic [[phenethylamine]] [[2C-C]]. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011.<ref name="doi10.1007/s00259-010-1686-8">{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | display-authors = 6 | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–693 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 }}

</ref> It acts as a potent [[agonist]] of the [[5HT2A receptor|5-HT_2A]] [[Receptor (biochemistry)|receptor]],<ref>{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–249 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}</ref> and has been studied in its [[Carbon-11|¹¹C]] [[isotopic labelling|radiolabelled]] form as a potential ligand for mapping the distribution of 5-HT_2A receptors in the brain, using [[positron emission tomography]] (PET).<ref name="doi10.1007/s00259-010-1686-8"/><ref>{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}</ref> Multiple deaths have occurred from usage of 25C-NBOMe due to the ease of accidental overdose. The long-term toxic effects of the drug have not been researched.

==History==

25C-NBOMe is derived from the psychedelic phenethylamine [[2C-C]] by substitution on the amine with a 2-methoxybenzyl group. 25C-NBOMe is a clumpy white powder with a notably bitter and metallic taste. 25C-NBOMe has been found on blotter mimics sold as LSD.<ref>{{cite journal | vauthors = Zuba D, Sekuła K, Buczek A | title = 25C-NBOMe--new potent hallucinogenic substance identified on the drug market | journal = Forensic Science International | volume = 227 | issue = 1–3 | pages = 7–14 | date = April 2013 | pmid = 22989597 | doi = 10.1016/j.forsciint.2012.08.027 }}</ref>

==Dosage==

25C-NBOMe is extremely potent and the effects of the drug increase greatly within a small window of dosage adjustment. Overdose may occur at as little as double an average dose. With inaccurate dosing of street [[Blotting paper|blotter paper]], when mistaken for LSD, or when taken as a powder or liquid, this has resulted in multiple accidental deaths.<ref>{{Cite journal | vauthors = Kamińska K, Świt P, Malek K |date=2020 |title=25C-NBOMe short characterisation |journal=Forensic Toxicology|volume=38 |issue=2 |pages=490–495 |doi=10.1007/s11419-020-00530-1 |s2cid=214704393 |doi-access=free }}</ref>

One study has shown that 25C-NBOMe blotters have 'hotspots' of the drug and the dosage is not evenly applied over the surface of the paper, which could lead to overdose.<ref>{{cite journal | vauthors = Lützen E, Holtkamp M, Stamme I, Schmid R, Sperling M, Pütz M, Karst U | title = Multimodal imaging of hallucinogens 25C- and 25I-NBOMe on blotter papers | journal = Drug Testing and Analysis | volume = 12 | issue = 4 | pages = 465–471 | date = April 2020 | pmid = 31846172 | doi = 10.1002/dta.2751 | s2cid = 209388281 | doi-access = free }}</ref> Sublingually, the threshold for the onset of hallucinogenic effects reportedly is about 100–250&nbsp;μg, with mild effects at 250–450, strong effects at 450–800, and very strong effects over 800&nbsp;μg.<ref>[http://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_dose.shtml 2C-C-NBOMe Dose] - [[erowid]]</ref>

NBOMe-substituted compounds have a diminished absorption rate passing through mucus membranes, but generally remain inactive when taken orally. [[Buccal administration|Buccal]], [[sublingual]] or [[insufflation (medicine)|insufflated]] routes of administration are all viable options. Absorption rate [[Buccal administration|buccally]] and [[sublingually]] can be increased when complexed with [[HPBCD]] complexing sugar, however the most efficient is [[nasal administration]], which shortens the duration while increasing intensity, but has been attributed to several overdoses and deaths.<ref name="Grautoff_2014">{{cite journal | vauthors = Grautoff S, Kähler J | title = [Near fatal intoxication with the novel psychoactive substance 25C-NBOMe] | language = de | journal = Medizinische Klinik, Intensivmedizin und Notfallmedizin | volume = 109 | issue = 4 | pages = 271–275 | date = May 2014 | pmid = 24770890 | doi = 10.1007/s00063-014-0360-5 }}</ref>

== Effects ==

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=== Desired ===

* strong open- and closed-eye [[hallucination|visuals]], including trails, color shifts, brightening, etc.

* mood lift

* [[euphoria]]

* mental and physical [[stimulation]]

* increase in associative & creative thinking

* increased awareness & appreciation of music

* life-changing spiritual experiences

* feelings of [[love]] and [[empathy]]

* increased [[pattern recognition (psychology)]]

* [[synesthesia]] and [[chromesthesia]] (intensified for those who experience these while sober)

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=== Neutral ===

* general change in [[consciousness]]

* [[mydriasis|pupil dilation]]

* unusual body sensations ([[paresthesia]], [[flushing (physiology)|flushing]], [[chills]], [[goose bumps]])

* change in perception of time, time dilation

* [[tachycardia|increased]] heart rate

* jaw clenching ([[bruxism]])

* [[yawning]], especially when coming up

* [[insomnia]]

* looping, [[recursion|recursive]], out-of-control thinking

* [[Dissociative|dissociation]]

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=== Undesired ===

(Includes negative side effects arising from overdose; likelihood of negative side effects increases with dose)

* [[confusion]] and difficulty focusing

* scrambled communication

* tunnel vision

* [[vasoconstriction]] leading to [[ischemia]]

* [[nausea]] and vomiting (normally only during the onset for those affected)

* [[paranoia]], [[fear]], and [[panic]]

* irritation of the throat

* irritation of mucous membranes

* upper respiratory irritation and difficulty breathing/swallowing

* unwanted and overwhelming feelings or life-changing spiritual experiences

* [[Syncope (medicine)|syncope]]

* [[tremor|shaking]]

* [[seizure]] (higher in NBOMes compared to other psychedelics).<ref name="pmid32174803">{{cite journal | journal = Frontiers in Neuroscience | vauthors = Jolanta Z, Monika K, and Piotr A | doi = 10.3389/fnins.2020.00078 | date = 26 February 2020 | volume = 14 | pmid = 32174803 | title = NBOMes–Highly Potent and Toxic Alternatives of LSD | page = 78 | doi-access = free | pmc = 7054380 }}</ref>

* [[dystonia]] and [[clonus]]

* [[death]]

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== Toxicity and harm potential ==

{{Excerpt | 25-NB | Toxicity and harm potential}}

===Neurotoxic and cardiotoxic actions===

{{Excerpt | 25-NB | Neurotoxic and cardiotoxic actions}}

===Emergency treatment===

{{Excerpt | 25-NB | Emergency treatment}}

==Drug prohibition laws==

===Canada===

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.<ref>{{cite web | url = https://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.html | title = Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) | website = Government of Canada | date = 4 May 2016 | access-date = 6 May 2023 | archive-url = https://web.archive.org/web/20220805234932/https://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.html | archive-date = 5 August 2022 | url-status = live}}</ref>

=== Israel ===

The NBOMe series of psychoactives became controlled in Israel in May, 2013.<ref name="erowid-law" /><ref>{{cite web |url=http://www.health.gov.il/English/Pages/HomePage.aspx |title=Amendment to Dangerous Drugs Ordinance |website=Israeli Ministry of Health |date=7 June 2013 |access-date=11 September 2015}}</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 [[2,5-Dimethoxy-4-bromoamphetamine|DOB]], and was therefore a Class C controlled drug analogue.<ref>[http://www.sciencemediacentre.co.nz/2012/03/13/legal-high-dime-not-so-legal/ 'Legal high' DIME not so legal. Science Media Centre, March 13th 2012]</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="erowid-law">{{cite web |url=https://www.erowid.org/chemicals/nbome/nbome_law.shtml |title=NBOMe Series Legal Status |publisher=Erowid |access-date=5 September 2015}}</ref><ref>{{cite web |url=http://www.rg.ru/2011/10/19/narko-dok.html |title=Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва |date=19 October 2011 |access-date=5 September 2015 |language=ru}}</ref>

=== Sweden ===

[[Riksdag|''Sveriges riksdag'']] added 25C-NBOMe to schedule I (''"substances, plant materials and fungi which normally do not have medical use"'') as narcotics in Sweden as of Aug 1, 2013, published by [[Medical Products Agency (Sweden)|''Medical Products Agency'']] in their regulation '''LVFS 2013:15''' listed as '''25C-NBOMe 2-(4-kloro-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin'''.<ref>{{cite web |url=https://lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf |title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika |date=24 July 2013 |access-date=5 September 2015 | vauthors = Åkerman CR }}</ref>

=== United Kingdom ===

{{N-benzylphenethylamine-Legality-United Kingdom}}

=== United States ===

Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.<ref>{{cite web |url=http://www.gpo.gov/fdsys/pkg/FR-2013-10-10/pdf/2013-24432.pdf |title=Proposed Rules |publisher=Drug Enforcement Administration (DEA) |date=10 October 2013 |access-date=5 September 2015 | vauthors = Harrigan TM }}</ref> In November 2015, the temporary scheduling was extended for another year.<ref name=pmid26567439>{{cite journal | author = Drug Enforcement Administration | title = Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order | journal = Federal Register | volume = 80 | issue = 219 | pages = 70657–70659 | date = November 2015 | pmid = 26567439 }}</ref>

=== China ===

As of October 2015 25C-NBOMe is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=1 October 2015 | url-status=dead }}</ref>

=== Czech Republic ===

25C-NBOMe is banned in the Czech Republic.<ref>{{cite web | url=http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | language=cs | access-date=2016-02-06 | archive-date=2016-03-09 | archive-url=https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | url-status=dead }}</ref>

==Analogues and derivatives==

{{2C-C analogues and derivatives}}

==Notes==

{{notelist}}

== References ==

{{reflist}}

{{Hallucinogens}}

{{Serotonin receptor modulators}}

{{Phenethylamines}}

[[Category:25-NB (psychedelics)]]

[[Category:Chlorobenzene derivatives]]

[[Category:Designer drugs]]