25C-NBOMe

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25C-NBOMe
2C-C-NBOMe-skeletal.svg
2C-C-NBOMe-spacefill.png
Systematic (IUPAC) name
2-(4-chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine
Clinical data
Legal status
Identifiers
CAS Number 1227608-02-7 N
PubChem CID: 46856354
ChemSpider 24583389 YesY
Chemical data
Formula C18H22ClNO3
Molecular mass 335.83 g·mol−1
  • COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl
  • InChI=1S/C18H22ClNO3/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:FJFPOGCVVLUYAQ-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

25C-NBOMe (NBOMe-2C-C, 2C-C-NBOMe, Cimbi-82) is a psychedelic drug and derivative of the psychedelic phenethylamine 2C-C. 25C-NBOMe appeared on online vendor sites in 2010 but was not reported in the literature until 2011.[1] It acts as a potent partial agonist for the 5HT2A receptor,[2] and has been studied in its 11C radiolabelled form as a potential ligand for mapping the distribution of 5-HT2A receptors in the brain, using positron emission tomography (PET).[1][3]

History

25C-NBOMe is derived from the psychedelic phenethylamine 2C-C by substitution on the amine with a 2-methoxybenzyl group. 25C-NBOMe is a clumpy white powder with a notably bitter and metallic taste. 25C-NBOMe has been found on blotter mimics sold as LSD.[4]

Dosage

Blotter paper containing 25C-NBOMe

Anecdotal reports from human users suggest 25C-NBOMe to be an active hallucinogen at a dose of as little as 200-500 µg insufflated and 300-600 µg buccaly (with threshold doses even lower), making it only half to a third the potency of LSD.[5] NBOMe-substituted compounds have a diminished absorption rate passing through mucus membranes, but generally remain inactive when taken orally. Buccal, sublingual or insufflated routes of administration are all viable options. Absorption rate buccally and sublingually can be increased when complexed with HPBCD complexing sugar, however the most efficient is nasal administration, which shortens the duration while increasing intensity, but has been attributed to several overdoses due to improper dosing.[6]

Effects

Toxicity and harm potential

25C-NBOMe overdoses have been linked to multi-organ failure.[6][7]

Drug prohibition laws

Israel

The NBOMe series of psychoactives became controlled in Israel in May, 2013.[8][9]

New Zealand

25C-NBOMe was sold as a designer drug in New Zealand in early 2012, but was withdrawn from sale after a statement by Associate Health Minister Peter Dunne that 25C-NBOMe would be considered to be substantially similar in chemical structure to the illegal hallucinogen DOB, and was therefore a Class C controlled drug analogue.[10]

Russia

Russia became the first country to regulate the NBOME class. The entire NBOMe series of psychoactives became controlled in the Russian Federation starting October, 2011.[8][11]

Sweden

Sveriges riksdag added 25C-NBOMe to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of Aug 1, 2013, published by Medical Products Agency in their regulation LVFS 2013:15 listed as 25C-NBOMe 2-(4-kloro-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin.[12]

United Kingdom

N-benzylated phenethylamines such as 25C-NBOMe were initially unaffected by the legal status of phenethylamine-class drugs.[13] The British government issued a temporary class drug order on a list of emerging recreational drugs, including 25C-NBOMe, on 4 June 2013. The order, which took effect on 10 June 2013 and will last for up to twelve months, prohibits the production, import and sale of “the NBOMe and Benzofury groups of substances”.[14]

United States

Several NBOMe series compounds will be temporarily scheduled in the United States for 2 years. The temporary scheduling applies to 25C-NBOMe, 25B-NBOMe, and 25I-NBOMe.[15] In November 2015, the temporary scheduling was extended for another year.[16]

China

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

Czech Republic

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

See also

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ 2C-C-NBOMe Dose - erowid
  6. ↑ 6.0 6.1 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. ↑ 8.0 8.1 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. ↑ ‘Legal high’ DIME not so legal. Science Media Centre, March 13th 2012
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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