25B-NBOMe

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25B-NBOMe
Legal status
Legal status
Identifiers
  • 2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H22BrNO3
Molar mass380.275 g/mol g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)Br)OC
  • InChI=1S/C18H22BrNO3/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 checkY
  • Key:SUXGNJVVBGJEFB-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 partial agonist for the 5HT2A receptor.[1][2][3][4] 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.[5][6][7] 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.[8][9]

Toxicity and harm potential

One case has been reported on where 25B-NBOMe was identified as the cause of death for a 17-year-old boy.[10]

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 300× lower than 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.[11]

Several deaths have been attributed to its close analogue 25I-NBOMe.

Legal status

Canada

As of October 31st, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada. http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php

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 Medical Products Agency in their regulation LVFS 2013:15 listed as 25B-NBOMe 2-(4-bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[12]

United States

In November 2013, the U.S. Drug Enforcement Administration placed 25B-NBOMe (along with 25I-NBOMe and 25C-NBOMe) temporarily in Schedule I of the Controlled Substances Act, making it an illicit drug for two years.[13] In November 2015, the temporary scheduling was extended for another year.[14]

China

As of October 2015 25B-NBOMe is a controlled substance in China.[15]

Czech Republic

25B-NBOMe is banned in the Czech Republic.[16]

See also

References

  1. ^ Ralf Heim (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. ^ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
  3. ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT(2A) receptor". Journal of Computer-aided Molecular Design. 25 (1): 51–66. doi:10.1007/s10822-010-9400-2. PMID 21088982.
  4. ^ Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (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. ^ Hansen, M. (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen.
  6. ^ 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. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. {{cite journal}}: Unknown parameter |displayauthors= ignored (|display-authors= suggested) (help)
  7. ^ Ettrup, A.; Holm, S. R.; Hansen, M.; Wasim, M.; Santini, M. A.; Palner, M.; Madsen, J.; Svarer, C.; Kristensen, J. L.; Knudsen, G. M. (2013). "Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand \11C]Cimbi-36". Molecular Imaging and Biology. 15 (4): 376–383. doi:10.1007/s11307-012-0609-4. PMID 23306971.
  8. ^ "From molecule to man: The full CIMBI-36 story" (PDF). http://www.cimbi.dk. Retrieved January 10, 2014. {{cite web}}: External link in |publisher= (help)
  9. ^ "Imanova announces the launch of a new imaging biomarker to investigate the serotonin system in psychiatric illness" (html). http://www.imanova.co.uk. Retrieved April 9, 2015. {{cite web}}: External link in |publisher= (help)
  10. ^ Roxas, Gabriel (February 19, 2015). "Designer Drug Identified As Cause Of Plano Teen's Death". CBS 11 News. Retrieved February 22, 2015.
  11. ^ Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand [11CCimbi-36]
  12. ^ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika;" (PDF) (in Swedish). http://www.lakemedelsverket.se. Retrieved October 4, 2013. {{cite web}}: External link in |publisher= (help)
  13. ^ http://www.justice.gov/dea/divisions/hq/2013/hq111513.shtml
  14. ^ Drug Enforcement Administration (2015). "Schedules of Controlled Substances: Extension of Temporary Placement of Three Synthetic Phenethylamines in Schedule I. Final order". Fed Regist. 80 (219): 70657–9. PMID 26567439.
  15. ^ "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.
  16. ^ "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.
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