25B-NBOMe
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Formula | C18H22BrNO3 |
Molar mass | 380.275 g/mol g·mol−1 |
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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 full agonist for the 5HT2A receptor.[1][2][3][4][5] 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.[6][7][8][9] 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.[10][11]
Toxicity and harm potential
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 only 1/300th 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.[12] One case has been reported on where 25B-NBOMe was identified as the cause of death for a 17-year-old boy.[13] The drug was also implicated in the death of an 18-year old male, however it was not reported whether the presence of the drug was confirmed postmortem.[14] Several deaths have been attributed to its close analogue 25I-NBOMe.
Analogues and derivatives
Analogues and derivatives of 2C-B:
25-N:
- 25B-NB
- 25B-NB23DM
- 25B-NB25DM
- 25B-NB3OMe
- 25B-NB4OMe
- 25B-NBF
- 25B-NBMD
- 25B-NBOH
- 25B-NBOMe (NBOMe-2CB)
- 2C-B-FLY
- 2CBFly-NBOMe (NBOMe-2CB-Fly)
- DOB-FLY
- DOB-2-DRAGONFLY-5-BUTTERFLY
Other:
- BOB
- BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB[17][18]
- BMB
- 2C-B-5-hemifly
- 2C-B-aminorex (2C-B-AR)
- 2C-B-AN
- 2C-B-BZP
- 2C-B-FLY-NB2EtO5Cl
- 2C-B-PP
- 2CB-Ind
- βk-2C-B (beta-keto 2C-B)
- N-Ethyl-2C-B
- TCB-2 (2C-BCB)
Legal status
Canada
As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.[19]
Russia
Banned as a narcotic drug since May 5, 2015.[20]
Sweden
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.[21]
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.[22]
United States
In November 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 illegal to manufacture, buy, possess, process, or distribute.[23]
China
As of October 2015 25B-NBOMe is a controlled substance in China.[24]
Czech Republic
25B-NBOMe is banned in the Czech Republic.[25]
References
- ^ Heim, Ralf (February 28, 2010). "Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts" (in German). diss.fu-berlin.de. Retrieved May 10, 2013.
{{cite web}}
: Unknown parameter|name-list-format=
ignored (|name-list-style=
suggested) (help) - ^ Silva, Maria (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (Ph.D. thesis). Universität Regensburg.
{{cite thesis}}
: Unknown parameter|name-list-format=
ignored (|name-list-style=
suggested) (help) - ^ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982.
- ^ Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL (March 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.
- ^ Ettrup A, da Cunha-Bang S, McMahon B, Lehel S, Dyssegaard A, Skibsted AW, et al. (July 2014). "Serotonin 2A receptor agonist binding in the human brain with [¹¹C]Cimbi-36". Journal of Cerebral Blood Flow and Metabolism. 34 (7): 1188–96. doi:10.1038/jcbfm.2014.68. PMC 4083382. PMID 24780897.
- ^ Hansen, M. (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen.
- ^ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM (April 2011). "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.
{{cite journal}}
: Unknown parameter|displayauthors=
ignored (|display-authors=
suggested) (help) - ^ Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM (August 2013). "Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [ 11C]Cimbi-36". Molecular Imaging and Biology. 15 (4): 376–83. doi:10.1007/s11307-012-0609-4. PMID 23306971.
- ^ Johansen A, Hansen HD, Svarer C, Lehel S, Leth-Petersen S, Kristensen JL, Gillings N, Knudsen GM (January 2017). "11C]Cimbi-36 labeled in two positions". Journal of Cerebral Blood Flow and Metabolism. Epub (4): 659–668. doi:10.1177/0271678X17746179. PMC 5888860. PMID 29215308.
- ^ "From molecule to man: The full CIMBI-36 story" (PDF). cimbi.dk. Retrieved January 10, 2014.
- ^ "Imanova announces the launch of a new imaging biomarker to investigate the serotonin system in psychiatric illness". imanova.co.uk. Retrieved April 9, 2015.
- ^ "Preclinical Safety Assessment of the 5-HT2A Receptor Agonist PET Radioligand [11C]Cimbi-36". bitnest.ca.
- ^ Roxas, Gabriel (February 19, 2015). "Designer Drug Identified As Cause Of Plano Teen's Death". CBS 11 News. Retrieved February 22, 2015.
{{cite news}}
: Unknown parameter|name-list-format=
ignored (|name-list-style=
suggested) (help) - ^ Hasnie, Aishah (April 1, 2014). "New synthetic drug investigated in Fishers teen's death". Fox 59. Retrieved January 3, 2018.
{{cite news}}
: Unknown parameter|name-list-format=
ignored (|name-list-style=
suggested) (help) - ^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
- ^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
- ^ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
- ^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
- ^ Gazette, Government of Canada, Public Works and Government Services Canada, Public Services and Procurement Canada, Integrated Services Branch, Canada. "Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)". gazette.gc.ca.
{{cite web}}
: CS1 maint: multiple names: authors list (link) - ^ "Постановление Правительства РФ от 30.06.1998 N 681 "Об утверждении перечня наркотических средств, психотропных веществ и их прекурсоров, подлежащих контролю в Российской Федерации" (с изменениями и дополнениями)". base.garant.ru.
- ^ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika;" (PDF). lakemedelsverket.se (in Swedish). Retrieved October 4, 2013.
- ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
- ^ "2016 - Final Rule: Placement of Three Synthetic Phenethylamines Into Schedule I". www.deadiversion.usdoj.gov. Retrieved April 2, 2018.
- ^ "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. September 27, 2015. Retrieved October 1, 2015.
- ^ "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.