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25C-NBOMe

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25C-NBOMe
Legal status
Legal status
Identifiers
  • 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H22ClNO3
Molar mass335.83 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:FJFPOGCVVLUYAQ-UHFFFAOYSA-N checkY
 ☒NcheckY (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

Canada

As of October 31st, 2016; 25C-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

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. ^ a b 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)
  2. ^ 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.
  3. ^ Hansen, M. (2011). "Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain". University of Copenhagen.
  4. ^ Zuba, D.; Sekuła, K.; Buczek, A. (2013). "25C-NBOMe – New potent hallucinogenic substance identified on the drug market". Forensic Science International. 227 (1–3): 7–14. doi:10.1016/j.forsciint.2012.08.027. PMID 22989597.
  5. ^ 2C-C-NBOMe Dose - erowid
  6. ^ a b S. Grautoff; J. Kähler (May 2014). "Lebensgefährliche Intoxikation mit der neuen psychoaktiven Substanz 25C-NBOMe". Medizinische Klinik - Intensivmedizin und Notfallmedizin (in German). 109 (4): 271–275. doi:10.1007/s00063-014-0360-5. PMID 24770890.
  7. ^ Tarpgaard M, Mærkedahl R, Lauridsen KB (August 2015). "Fatalt forløb efter intoksikation med det nye designerdrug 25C-NBOMe". Ugeskrift for Laeger (in Danish). 177. PMID 26324189.
  8. ^ a b "NBOMe Series Legal Status". Erowid. Retrieved 5 September 2015.
  9. ^ "Amendment to Dangerous Drugs Ordinance". Israeli Ministry of Health. 7 June 2013. Retrieved 11 September 2015.
  10. ^ ‘Legal high’ DIME not so legal. Science Media Centre, March 13th 2012
  11. ^ "Постановление Правительства Российской Федерации от 6 октября 2011 г. N 822 г. Москва" (in Russian). 19 October 2011. Retrieved 5 September 2015.
  12. ^ Generaldirektör Ch ristina Rångemark Åkerman (24 July 2013). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF). Retrieved 5 September 2015.
  13. ^ Advisory Council on the Misuse of Drugs (2013-05-29). "Temporary Class Drug Order Report on 5-6APB and NBOMe compounds" (PDF). Gov.Uk. Retrieved 2013-06-16.
  14. ^ "'NBOMe' and 'Benzofury' banned". gov.uk. 2013-06-04. Retrieved 2013-06-10.
  15. ^ Thomas M. Harrigan (10 October 2013). "Proposed Rules" (PDF). Drug Enforcement Administration (DEA). Retrieved 5 September 2015.
  16. ^ 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.
  17. ^ "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. 27 September 2015. Retrieved 1 October 2015.
  18. ^ "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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