25B-NBOMe

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25B-NBOMe
2C-B-NBOMe-skeletal.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H22BrNO3
Molar mass380.275 g/mol g·mol−1
3D model (JSmol)
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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][4][5] Anecdotal reports from users[citation needed] suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 µg,[citation needed] making it a similar potency to other phenethylamine derived hallucinogens such as Bromo-DragonFLY. Duration of effects lasts about 12–16 hours.[citation needed]

The carbon-11 labeled version of this compound ([11C]Cimbi-36) was synthesized and validated as a radioactive tracer for positron emission tomography (PET) in Copenhagen.[6][7][8][9] As a 5-HT2A receptor agonist PET radioligand, [11C]Cimbi-36 was hypothesized to provide a more functional marker of these receptors. Also, [11C]Cimbi-36 is investigated as a potential marker of serotonin release and thus could serve as an indicator of serotonin levels in vivo. [11C]Cimbi-36 is now undergoing clinical trials as a PET-ligand in humans.[10][11][12]

Toxicity and harm potential[edit]

25B-NBOMe has been used in clinical trials with an evaluation dose for safety consideration to humans of only 1 microgram. Such a dose is only 1/300th the dose expected to be hallucinogenic to humans and it is expected that recreational use would greatly exceed doses determined to be safe to humans.[13] One case has been reported on where 25B-NBOMe was identified as the cause of death for a 17-year-old boy.[14] The drug was also implicated in the death of an 18-year old male, however it was not reported whether the presence of the drug was confirmed postmortem.[15] Several deaths have been attributed to its close analogue 25I-NBOMe.

Analogues and derivatives[edit]

Legal status[edit]

Canada[edit]

As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.[16]

Russia[edit]

Banned as a narcotic drug since May 5, 2015.[17]

Sweden[edit]

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 Medical Products Agency in their regulation LVFS 2013:15 listed as 25B-NBOMe 2-(4-bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[18]

United Kingdom[edit]

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[19]


United States[edit]

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.[20]

China[edit]

As of October 2015 25B-NBOMe is a controlled substance in China.[21]

Czech Republic[edit]

25B-NBOMe is banned in the Czech Republic.[22]

References[edit]

  1. ^ Heim R (February 28, 2010). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts" (in German). diss.fu-berlin.de. Retrieved May 10, 2013.
  2. ^ Silva M (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (Ph.D. thesis). Universität Regensburg.
  3. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  4. ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 2014). "Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
  5. ^ Ettrup A, da Cunha-Bang S, McMahon B, Lehel S, Dyssegaard A, Skibsted AW, et al. (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. doi:10.1038/jcbfm.2014.68. PMC 4083382. PMID 24780897.
  6. ^ Hansen, M. (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. Archived October 22, 2013, at the Wayback Machine PhD Thesis, University of Copenhagen.
  7. ^ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, et al. (April 2011). "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. doi:10.1007/s00259-010-1686-8. PMID 21174090.
  8. ^ Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM (August 2013). "Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [ 11C]Cimbi-36". Molecular Imaging and Biology. 15 (4): 376–83. doi:10.1007/s11307-012-0609-4. PMID 23306971.
  9. ^ Johansen A, Hansen HD, Svarer C, Lehel S, Leth-Petersen S, Kristensen JL, Gillings N, Knudsen GM (January 2017). "11C]Cimbi-36 labeled in two positions". Journal of Cerebral Blood Flow and Metabolism. Epub (4): 659–668. doi:10.1177/0271678X17746179. PMC 5888860. PMID 29215308.
  10. ^ "From molecule to man: The full CIMBI-36 story" (PDF). cimbi.dk. Retrieved January 10, 2014.
  11. ^ "Imanova announces the launch of a new imaging biomarker to investigate the serotonin system in psychiatric illness". imanova.co.uk. Archived from the original on April 9, 2015. Retrieved April 9, 2015.
  12. ^ Madsen, Martin K.; Fisher, Patrick M.; Burmester, Daniel; Dyssegaard, Agnete; Stenbæk, Dea S.; Kristiansen, Sara; Johansen, Sys S.; Lehel, Sczabolz; Linnet, Kristian (January 26, 2019). "Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels". Neuropsychopharmacology. doi:10.1038/s41386-019-0324-9. ISSN 0893-133X. PMID 30685771.
  13. ^ "Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand [11C]Cimbi-36". bitnest.ca.[permanent dead link]
  14. ^ Roxas G (February 19, 2015). "Designer Drug Identified As Cause Of Plano Teen's Death". CBS 11 News. Retrieved February 22, 2015.
  15. ^ Hasnie A (April 1, 2014). "New synthetic drug investigated in Fishers teen's death". Fox 59. Retrieved January 3, 2018.
  16. ^ Gazette, Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada. "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". gazette.gc.ca.
  17. ^ "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.
  18. ^ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika;" (PDF). lakemedelsverket.se (in Swedish). Retrieved October 4, 2013.
  19. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
  20. ^ "2016 - Final Rule: Placement of Three Synthetic Phenethylamines Into Schedule I". www.deadiversion.usdoj.gov. Retrieved April 2, 2018.
  21. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. September 27, 2015. Retrieved October 1, 2015.
  22. ^ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví.