25B-NBOMe

25B-NBOMe

25B-NBOMe
Systematic (IUPAC) name
2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Clinical data
Legal status
Identifiers
CAS Registry Number  N
PubChem CID:
ChemSpider  YesY
Chemical data
Formula C18H22BrNO3
Molecular mass 380.275 g/mol
 N   

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 suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500 µg, making it a similar potency to other phenethylamine derived hallucinogens such as bromo-dragonfly. Duration of effects lasts about 12–16 hours.

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

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]

On November 15, 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 an illicit drug.[13]

As of October 2015 25B-NBOMe is a controlled substance in China.[14]

See also

References

  1. ^
  2. ^ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
  3. ^
  4. ^
  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. ^
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  9. ^
  10. ^
  11. ^ Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand [11CCimbi-36]
  12. ^
  13. ^ http://www.justice.gov/dea/divisions/hq/2013/hq111513.shtml
  14. ^