View source for Chemistry:25B-NBOMe

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 477215941
| IUPAC_name = 2-(4-bromo-2,5-dimethoxyphenyl)-''N''-[(2-methoxyphenyl)methyl]ethanamine
| image = 2C-B-NBOMe-skeletal.svg

<!--Clinical data-->
| tradename =
| legal_BR = F2
| legal_UK = Class A
| legal_US =Schedule I
| legal_DE = Anlage I
| legal_UN = P I 
| legal_UN_comment = <ref>{{Cite web |title=Substance Details 25B-NBOMe |url=https://www.unodc.org/LSS/Substance/Details/8a781e2b-b49a-4baa-b71f-ad1124864662 |access-date=2024-01-22}}</ref>

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 1026511-90-9

| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = S6NAA81PHK

| PubChem = 9977044
| KEGG = C22773
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8152636

<!--Chemical data-->
| C=18 | H=22 | Br=1 | N=1 | O=3 
| smiles = COC1=CC=CC=C1CNCCC2=CC(=C(C=C2OC)Br)OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SUXGNJVVBGJEFB-UHFFFAOYSA-N
}}
'''25B-NBOMe''' ('''NBOMe-2C-B''', '''Cimbi-36''', '''Nova''', '''BOM 2-CB''') is a derivative of the [[Biology:Phenethylamine|phenethylamine]] [[Chemistry:Psychedelic drug|psychedelic]] [[Chemistry:2C-B|2C-B]], discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT<sub>2A</sub> [[Biology:Receptor (biochemistry)|receptor]].<ref name=ralfheim>{{cite web | vauthors = Heim R | title = Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |publisher=diss.fu-berlin.de |date=February 28, 2010 |language=de |access-date=2013-05-10}}</ref><ref>{{cite thesis | vauthors = Silva M | degree = Ph.D. | url = http://epub.uni-regensburg.de/12119/ | title = Theoretical study of the interaction of agonists with the 5-HT2A receptor | publisher = Universität Regensburg | date = 2009 }}</ref><ref name="pmid21088982">{{cite journal | vauthors = Silva ME, Heim R, Strasser A, Elz S, Dove S | title = Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor | journal = Journal of Computer-Aided Molecular Design | volume = 25 | issue = 1 | pages = 51–66 | date = January 2011 | pmid = 21088982 | doi = 10.1007/s10822-010-9400-2 | bibcode = 2011JCAMD..25...51S | citeseerx = 10.1.1.688.2670 | s2cid = 3103050 }}</ref><ref>{{cite journal | vauthors = Hansen M, Phonekeo K, Paine JS, Leth-Petersen S, Begtrup M, Bräuner-Osborne H, Kristensen JL | title = Synthesis and structure-activity relationships of N-benzyl phenethylamines as 5-HT2A/2C agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–9 | date = March 2014 | pmid = 24397362 | pmc = 3963123 | doi = 10.1021/cn400216u }}</ref><ref name=":0">{{cite journal | vauthors = Ettrup A, da Cunha-Bang S, McMahon B, Lehel S, Dyssegaard A, Skibsted AW, Jørgensen LM, Hansen M, Baandrup AO, Bache S, Svarer C, Kristensen JL, Gillings N, Madsen J, Knudsen GM | display-authors = 6 | title = Serotonin 2A receptor agonist binding in the human brain with [¹¹C]Cimbi-36 | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 34 | issue = 7 | pages = 1188–96 | date = July 2014 | pmid = 24780897 | pmc = 4083382 | doi = 10.1038/jcbfm.2014.68 }}</ref>{{Excessive citations inline|date=December 2022}} Anecdotal reports from users{{Weasel inline|date=December 2022}} suggest 25B-NBOMe to be an active hallucinogen at a dose of as little as 250–500&nbsp;µg,{{Citation needed|date=July 2012}} making it a similar potency to other phenethylamine derived hallucinogens such as [[Chemistry:Bromo-DragonFLY|Bromo-DragonFLY]]. Duration of effects lasts about 12–16 hours{{Citation needed|date=July 2012}}, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses.<ref name=":0" /> Recently, Custodio et al (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.<ref>{{cite journal | vauthors = Custodio RJ, Sayson LV, Botanas CJ, Abiero A, You KY, Kim M, Lee HJ, Yoo SY, Lee KW, Lee YS, Seo JW, Ryu IS, Kim HJ, Cheong JH | display-authors = 6 | title = 25B-NBOMe, a novel N-2-methoxybenzyl-phenethylamine (NBOMe) derivative, may induce rewarding and reinforcing effects via a dopaminergic mechanism: Evidence of abuse potential | journal = Addiction Biology | volume = 25 | issue = 6 | pages = e12850 | date = November 2020 | pmid = 31749223 | doi = 10.1111/adb.12850 | s2cid = 208217863 }}</ref>

The carbon-11 labeled version of this compound ([<sup>11</sup>C]Cimbi-36) was synthesized and validated as a [[Biology:Radioactive tracer|radioactive tracer]] for positron emission tomography (PET) in Copenhagen.<ref>{{cite thesis | vauthors = Hansen M | title = Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. | degree = Ph.D. | publisher = University of Copenhagen | date = 2010-12-16 | doi = 10.13140/RG.2.2.33671.14245}}</ref><ref>{{cite journal | vauthors = Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, Lehel S, Herth MM, Madsen J, Kristensen J, Begtrup M, Knudsen GM | title = Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers | journal = European Journal of Nuclear Medicine and Molecular Imaging | volume = 38 | issue = 4 | pages = 681–93 | date = April 2011 | pmid = 21174090 | doi = 10.1007/s00259-010-1686-8 | s2cid = 12467684 | display-authors = 9 }}
</ref><ref>{{cite journal | vauthors = Ettrup A, Holm S, Hansen M, Wasim M, Santini MA, Palner M, Madsen J, Svarer C, Kristensen JL, Knudsen GM | display-authors = 6 | title = Preclinical safety assessment of the 5-HT2A receptor agonist PET radioligand [ 11C]Cimbi-36 | journal = Molecular Imaging and Biology | volume = 15 | issue = 4 | pages = 376–383 | date = August 2013 | pmid = 23306971 | doi = 10.1007/s11307-012-0609-4 | s2cid = 1474367 }}</ref><ref>{{cite journal | vauthors = Johansen A, Hansen HD, Svarer C, Lehel S, Leth-Petersen S, Kristensen JL, Gillings N, Knudsen GM | display-authors = 6 | title = The importance of small polar radiometabolites in molecular neuroimaging: A PET study with [<sup>11</sup>C]Cimbi-36 labeled in two positions | journal = Journal of Cerebral Blood Flow and Metabolism | volume = 38 | issue = 4 | pages = 659–668 | date = April 2018 | pmid = 29215308 | pmc = 5888860 | doi = 10.1177/0271678X17746179 }}</ref><ref>{{cite journal | vauthors = Johansen A, Holm S, Dall B, Keller S, Kristensen JL, Knudsen GM, Hansen HD | title = Human biodistribution and radiation dosimetry of the 5-HT<sub>2A</sub> receptor agonist Cimbi-36 labeled with carbon-11 in two positions | journal = EJNMMI Research | volume = 9 | issue = 1 | page = 71 | date = July 2019 | pmid = 31367837 | pmc = 6669221 | doi = 10.1186/s13550-019-0527-4 | doi-access = free }}</ref>{{Excessive citations inline|date=December 2022}} As a 5-HT<sub>2A</sub> receptor agonist PET radioligand, [<sup>11</sup>C]Cimbi-36 was hypothesized to provide a more functional marker of these receptors. Also, [<sup>11</sup>C]Cimbi-36 is investigated as a potential marker of serotonin release and thus could serve as an indicator of serotonin levels [[Biology:In vivo|in vivo]]. [<sup>11</sup>C]Cimbi-36 is now undergoing clinical trials as a PET-ligand in humans.<ref>{{cite web|url=http://www.cimbi.dk/images/stories/files/The_full_Cimbi36_story.pdf |title=From molecule to man: The full CIMBI-36 story |work=cimbi.dk |access-date=2014-01-10 }}</ref><ref>{{cite web |url=http://www.imanova.co.uk/news-and-publications/imanova-news/entry/imanova-announces-the-launch-of-a-new-imaging-biomarker-to-investigate-the-serotonin-system-in-psychiatric-illness.html |title=Imanova announces the launch of a new imaging biomarker to investigate the serotonin system in psychiatric illness |work=imanova.co.uk |access-date=2015-04-09 |archive-url=https://archive.today/20150409133929/http://www.imanova.co.uk/news-and-publications/imanova-news/entry/imanova-announces-the-launch-of-a-new-imaging-biomarker-to-investigate-the-serotonin-system-in-psychiatric-illness.html |archive-date=April 9, 2015 |df=mdy-all }}</ref><ref>{{cite journal | vauthors = Madsen MK, Fisher PM, Burmester D, Dyssegaard A, Stenbæk DS, Kristiansen S, Johansen SS, Lehel S, Linnet K, Svarer C, Erritzoe D, Ozenne B, Knudsen GM | display-authors = 6 | title = Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels | journal = Neuropsychopharmacology | volume = 44 | issue = 7 | pages = 1328–1334 | date = June 2019 | pmid = 30685771 | pmc = 6785028 | doi = 10.1038/s41386-019-0324-9 }}</ref>

==Toxicity and harm potential==
{{Excerpt | 25-NB | Toxicity and harm potential}}
===Neurotoxic and cardiotoxic actions===
{{Excerpt | 25-NB | Neurotoxic and cardiotoxic actions}}
===Emergency treatment===
{{Excerpt | 25-NB | Emergency treatment}}

===Analogues and derivatives===
{{2C-B analogues and derivatives}}

== Legal status ==

===Canada===
As of October 31, 2016; 25B-NBOMe is a controlled substance (Schedule III) in Canada.<ref>{{cite periodical |url=http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php |periodical=Canada Gazette |volume=150 |issue=9 |title=Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines) |date=4 May 2016|url-status=live|archive-url=https://web.archive.org/web/20160831014117/http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php|archive-date=2016-08-31}}</ref>

===Russia===
Banned as a narcotic drug since May 5, 2015.<ref>{{cite web|url=http://base.garant.ru/12112176/|title=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)|website=base.garant.ru}}</ref>

===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 the [[Organization:Medical Products Agency (Sweden)|Medical Products Agency]] in their regulation LVFS 2013:15 listed as ''25B-NBOMe 2-(4-bromo-2,5-dimetoxifenyl)-N-(2-metoxibensyl)etanamin''.<ref>{{cite web|url=http://www.lakemedelsverket.se/upload/lvfs/LVFS_2013-15.pdf |title=Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika; |work=lakemedelsverket.se |access-date=2013-10-04 |language=sv}}</ref>

===United Kingdom===
{{N-benzylphenethylamine-Legality-United Kingdom}}

===United States===
In November 2013, the U.S. Drug Enforcement Administration placed 25B-NBOMe (along with [[Chemistry:25I-NBOMe|25I-NBOMe]] and [[Chemistry:25C-NBOMe|25C-NBOMe]]) in Schedule I of the Controlled Substances Act, making it illegal to manufacture, buy, possess, process, or distribute.<ref>{{Cite web|url=https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr0927_2.htm|title=2016 - Final Rule: Placement of Three Synthetic Phenethylamines Into Schedule I|website=www.deadiversion.usdoj.gov|language=en-US|access-date=2018-04-02}}</ref>

===China===
As of October 2015 25B-NBOMe is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=zh | access-date=1 October 2015 | archive-url=https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html | archive-date=October 1, 2015 }}</ref>

===Czech Republic===
25B-NBOMe is banned in the Czech Republic.<ref>{{cite web | url=http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | language=cs | access-date=February 6, 2016 | archive-date=March 9, 2016 | archive-url=https://web.archive.org/web/20160309174659/http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf }}</ref>

==Notes==
{{notelist}}

== References ==
{{reflist}}

{{Hallucinogenic phenethylamines}}

[[Category:Designer drugs]]
[[Category:Bromoarenes]]

{{Sourceattribution|25B-NBOMe}}