25B-NBOMe explained

25B-NBOMe (NBOMe-2C-B, Cimbi-36, Nova, BOM 2-CB) is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor.[1] [2] [3] Duration of effects lasts about 3–10 hours,[4] although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses.[5] Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.[6]

The carbon-11 labeled version of this compound ([<sup>11</sup>C]Cimbi-36) was synthesized and validated as a radioactive tracer for positron emission tomography (PET) in Copenhagen.[7] [8] [9] As a 5-HT2A receptor agonist PET radioligand, [<sup>11</sup>C]Cimbi-36 was hypothesized to provide a more functional marker of these receptors. Also, [<sup>11</sup>C]Cimbi-36 is investigated as a potential marker of serotonin release and thus could serve as an indicator of serotonin levels in vivo. [<sup>11</sup>C]Cimbi-36 is now undergoing clinical trials as a PET-ligand in humans.[10] [11] [12]

Toxicity and harm potential

Analogues and derivatives

Legal status

Canada

As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.[13]

Russia

Banned as a narcotic drug since May 5, 2015.[14]

Sweden

In Sweden, the Riksdag added 25B-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of August 1, 2013, published by the Medical Products Agency in their regulation LVFS 2013:15 listed as 25B-NBOMe 2-(4-bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[15]

United States

In November 2013, the U.S. Drug Enforcement Administration placed 25B-NBOMe (along with 25I-NBOMe and 25C-NBOMe) in Schedule I of the Controlled Substances Act, making it illegal to manufacture, buy, possess, process, or distribute.[16]

China

As of October 2015 25B-NBOMe is a controlled substance in China.[17]

Czech Republic

25B-NBOMe is banned in the Czech Republic.[18]

Notes and References

  1. Silva M . Ph.D. . Theoretical study of the interaction of agonists with the 5-HT2A receptor . Universität Regensburg . 2009 .
  2. Silva ME, Heim R, Strasser A, Elz S, Dove S . Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor . Journal of Computer-Aided Molecular Design . 25 . 1 . 51–66 . January 2011 . 21088982 . 10.1007/s10822-010-9400-2 . 2011JCAMD..25...51S . 10.1.1.688.2670 . 3103050 .
  3. Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL . Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists . ACS Chemical Neuroscience . 5 . 3 . 243–9 . March 2014 . 24397362 . 3963123 . 10.1021/cn400216u .
  4. Francesco SB, Ornella C, Gabriella A, Giuseppe V, Rita S, Flaminia BP, Eduardo C, Pierluigi S, Giovanni M, Guiseppe B, Fabrizio S . 3 July 2014 . 25C-NBOMe: preliminary data on pharmacology, psychoactive effects, and toxicity of a new potent and dangerous hallucinogenic drug . BioMed Research International . 2014 . 734749 . 10.1155/2014/734749 . 4106087 . 25105138 . free.
  5. 6 . Ettrup A, da Cunha-Bang S, McMahon B, Lehel S, Dyssegaard A, Skibsted AW, Jørgensen LM, Hansen M, Baandrup AO, Bache S, Svarer C, Kristensen JL, Gillings N, Madsen J, Knudsen GM . July 2014 . Serotonin 2A receptor agonist binding in the human brain with [¹¹C]Cimbi-36 . Journal of Cerebral Blood Flow and Metabolism . 34 . 7 . 1188–96 . 10.1038/jcbfm.2014.68 . 4083382 . 24780897.
  6. Custodio RJ, Sayson LV, Botanas CJ, Abiero A, You KY, Kim M, Lee HJ, Yoo SY, Lee KW, Lee YS, Seo JW, Ryu IS, Kim HJ, Cheong JH . 6 . 25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential . Addiction Biology . 25 . 6 . e12850 . November 2020 . 31749223 . 10.1111/adb.12850 . 208217863 .
  7. Hansen M . Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. . Ph.D. . University of Copenhagen . 2010-12-16 . 10.13140/RG.2.2.33671.14245.
  8. Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM . Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers . European Journal of Nuclear Medicine and Molecular Imaging . 38 . 4 . 681–93 . April 2011 . 21174090 . 10.1007/s00259-010-1686-8 . 12467684 . 9 .
  9. Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM . 6 . Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [11C]Cimbi-36 . Molecular Imaging and Biology . 15 . 4 . 376–383 . August 2013 . 23306971 . 10.1007/s11307-012-0609-4 . 1474367 .
  10. Web site: From molecule to man: The full CIMBI-36 story . cimbi.dk . 2014-01-10 .
  11. Web site: Imanova announces the launch of a new imaging biomarker to investigate the serotonin system in psychiatric illness . imanova.co.uk . 2015-04-09 . https://archive.today/20150409133929/http://www.imanova.co.uk/news-and-publications/imanova-news/entry/imanova-announces-the-launch-of-a-new-imaging-biomarker-to-investigate-the-serotonin-system-in-psychiatric-illness.html . April 9, 2015 . mdy-all .
  12. Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, Johansen SS, Lehel S, Linnet K, Svarer C, Erritzoe D, Ozenne B, Knudsen GM . 6 . Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels . Neuropsychopharmacology . 44 . 7 . 1328–1334 . June 2019 . 30685771 . 6785028 . 10.1038/s41386-019-0324-9 .
  13. Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) . Canada Gazette . 150 . 9 . 4 May 2016. live. https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php. 2016-08-31.
  14. Web site: Постановление Правительства РФ от 30.06.1998 N 681 "Об утверждении перечня наркотических средств, психотропных веществ и их прекурсоров, подлежащих контролю в Российской Федерации" (с изменениями и дополнениями). base.garant.ru.
  15. Web site: Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika; . lakemedelsverket.se . 2013-10-04 . sv.
  16. Web site: 2016 - Final Rule: Placement of Three Synthetic Phenethylamines Into Schedule I. www.deadiversion.usdoj.gov. en-US. 2018-04-02. May 13, 2017. https://web.archive.org/web/20170513140029/https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr0927_2.htm. dead.
  17. Web site: 关于印发《非药用类麻醉药品和精神药品列管办法》的通知 . China Food and Drug Administration . 27 September 2015 . zh . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . October 1, 2015 .
  18. Web site: Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) . Ministerstvo zdravotnictví . cs . February 6, 2016 . March 9, 2016 . https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf .

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