25C-NBOMe

{{Short description|Psychedelic drug}}

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

{{Drugbox

| Verifiedfields = verified

| Watchedfields = verified

| verifiedrevid = 451565314

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

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

| width = 200px

| width2 = 200px

| tradename =

| routes_of_administration = Sublingual, others

| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen

| ATC_prefix = None

| ATC_suffix =

| legal_status =

| legal_BR = F2

| legal_BR_comment = {{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}}

| legal_DE = Anlage I

| legal_US = Schedule I

| legal_UK = Class A

| legal_UN = P I

| legal_UN_comment = {{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}}

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1227608-02-7

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

| UNII = 9FGW3C260N

| PubChem = 46856354

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

| KEGG = C22720

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 24583389

| synonyms = NBOMe-2C-C; 2C-C-NBOMe; Cimbi-82

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

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

| SMILES = COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H22ClNO3/c1-21-16-7-5-4-6-14(16)12-20-9-8-13-10-18(23-3)15(19)11-17(13)22-2/h4-7,10-11,20H,8-9,12H2,1-3H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FJFPOGCVVLUYAQ-UHFFFAOYSA-N

}}

25C-NBOMe, also known as NBOMe-2C-C, 2C-C-NBOMe, or Cimbi-82, is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. It acts as a potent agonist of the 5-HT2A receptor,{{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 }} and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).{{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}} 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. 25C-NBOMe was first described in the scientific literature by 2010.Ettrup, A. (2010). Serotonin receptor studies in the pig brain: pharmacological intervention and positron emission tomography tracer development (Doctoral dissertation, Faculty of Health Sciences, University of Copenhagen). https://research.regionh.dk/en/publications/serotonin-receptor-studies-in-the-pig-brain-pharmacological-inter{{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 }}

Use

File:25C-NBOMe blotter.jpg

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 blotter paper, when mistaken for LSD, or when taken as a powder or liquid, this has resulted in multiple accidental deaths.{{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 }}

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.{{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 }} Sublingually, the threshold for the onset of hallucinogenic effects reportedly is about 100–250 μg, with mild effects at 250–450, strong effects at 450–800, and very strong effects over 800 μg.[http://www.erowid.org/chemicals/2cc_nbome/2cc_nbome_dose.shtml 2C-C-NBOMe Dose] - erowid

NBOMe-substituted compounds have a diminished absorption rate passing through mucous membranes, but generally remain inactive when taken orally. Buccal, sublingual or insufflated routes of administration are all viable options. Absorption rate 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.{{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 }}

Effects

{{col-begin}}

{{col-break}}

=Desired=

{{col-break}}

=Neutral=

{{col-break}}

=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
  • shaking
  • seizure (higher in NBOMes compared to other psychedelics).{{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 }}
  • dystonia and clonus
  • death

{{col-end}}

Interactions

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

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}}

Pharmacology

25C-NBOMe acts as a serotonin 5-HT2 receptor agonist, including of the serotonin 5-HT2A receptor.

Chemistry

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.

=Analogues and derivatives=

{{2C-C analogues and derivatives}}

History

{{See also|25-NB#History}}

25C-NBOMe was first described in the scientific literature by Anders Ettrup and colleagues by 2010.

Society and culture

=Recreational use=

25C-NBOMe has been found on blotter mimics sold as LSD.{{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 }}

=Legal status=

==Canada==

As of October 31, 2016; 25C-NBOMe is a controlled substance (Schedule III) in Canada.{{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}}

==China==

As of October 2015, 25C-NBOMe is a controlled substance in China.{{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 }}

==Czech Republic==

25C-NBOMe is banned in the Czech Republic.{{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 }}

==Israel==

The NBOMe series of psychoactives became controlled in Israel in May, 2013.{{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}}

==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.[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]

==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.{{cite web |url=https://www.erowid.org/chemicals/nbome/nbome_law.shtml |title=NBOMe Series Legal Status |publisher=Erowid |access-date=5 September 2015}}{{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}}

==Sweden==

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 in their regulation LVFS 2013:15 listed as 25C-NBOMe 2-(4-kloro-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.{{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 }}

==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.{{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 }} In November 2015, the temporary scheduling was extended for another year.{{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 }}

Notes

{{Notelist}}

References

{{Reflist}}