25B-NBOMe

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25B-NBOMe
2C-B-NBOMe-skeletal.svg
Systematic (IUPAC) name
2-(4-bromo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Clinical data
Legal status
Identifiers
CAS Number 1026511-90-9 N
PubChem CID: 9977044
ChemSpider 8152636 YesY
Chemical data
Formula C18H22BrNO3
Molecular mass 380.275 g/mol
  • 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 YesY
  • Key:SUXGNJVVBGJEFB-UHFFFAOYSA-N YesY
 NYesY (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

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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand [11CCimbi-36]
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ http://www.justice.gov/dea/divisions/hq/2013/hq111513.shtml
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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