25C-NBOMe

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 agonist for the 5HT_2A receptor,[2] and has been studied in its ¹¹C radiolabelled form as a potential ligand for mapping the distribution of 5-HT_2A receptors in the brain, using positron emission tomography (PET).[1][3]

25C-NBOMe

Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
IUPAC name 2-(4-Chloro-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine
CAS Number	1227608-02-7^N
PubChem CID	46856354
ChemSpider	24583389^Y
UNII	9FGW3C260N
CompTox Dashboard (EPA)	DTXSID10676790
Chemical and physical data
Formula	C18H22ClNO3
Molar mass	335.83 g·mol^−1
3D model (JSmol)	Interactive image
SMILES COc2ccccc2CNCCc(cc1OC)c(OC)cc1Cl
InChI 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^Y Key:FJFPOGCVVLUYAQ-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

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 buccally (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

Desired strong open- and closed-eye visuals, including trails, color shifts, brightening, etc. mood lift euphoria mental and physical stimulation increase in associative & creative thinking increased awareness & appreciation of music life-changing spiritual experiences feelings of love and empathy increased pattern recognition (psychology) synesthesia and chromesthesia (intensified for those who experience these while sober)

Neutral general change in consciousness pupil dilation unusual body sensations (paresthesia, flushing, chills, goose bumps) change in perception of time, time dilation increased heart rate jaw clenching (bruxism) yawning, especially when coming up insomnia looping, recursive, out-of-control thinking dissociation

Undesired (Includes negative side effects arising from overdose; likelihood of negative side effects increases with dose) confusion and difficulty focusing scrambled communication tunnel vision vasoconstriction nausea and vomiting (normally only during the onset for those affected) paranoia, fear, and panic irritation of the throat irritation of mucous membranes upper respiratory irritation and difficulty breathing/swallowing unwanted and overwhelming feelings or life-changing spiritual experiences syncope shaking dystonia, clonus and seizure death

Toxicity and harm potential

25C-NBOMe overdoses have been linked to multi-organ failure. It is a substituted para-Chloroamphetamine which is a known neurotoxin, 25C-NBOMe being much more potent and a direct serotonergic neurotoxic agent. [6][7]

Drug prohibition laws

Canada

As of October 31, 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

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[13]

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.[14] In November 2015, the temporary scheduling was extended for another year.[15]

China

As of October 2015 25C-NBOMe is a controlled substance in China.[16]

Czech Republic

25C-NBOMe is banned in the Czech Republic.[17]

Analogues and derivatives

Analogues and derivatives of 2C-C:

25C-NB*:

• 25C-NBF
• 25C-NBMD
• 25C-NBOH
• 25C-NBOMe (NBOMe-2CC)
• 25C-NB3OMe
• 25C-NB4OMe

References

1. Ettrup, A.; Hansen, M.; Santini, M. A.; Paine, J.; Gillings, N.; Palner, M.; Lehel, S.; Herth, M. M.; Madsen, J.; et al. (2010). "Radiosynthesis and in vivo evaluation of a series of substituted ¹¹C-phenethylamines as 5-HT_2A agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090.
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-HT_2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
3. Hansen M (2010-12-16). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (Ph.D. thesis). University of Copenhagen. doi:10.13140/RG.2.2.33671.14245.
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. 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 (35). PMID 26324189.
8. "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. "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
14. Thomas M. Harrigan (10 October 2013). "Proposed Rules" (PDF). Drug Enforcement Administration (DEA). Retrieved 5 September 2015.
15. 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.
16. "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
17. "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.