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βk-2C-B

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
βk-2C-B
Clinical data
Other namesβ-Keto-2C-B; bk-2C-B; 4-bromo-2,5-dimethoxy-β-ketophenethylamine; 2,5-Dimethoxy-4-bromo-β-ketophenethylamine
Routes of
administration
Oral, others[1]
Drug classSerotonin receptor modulator;Serotonin 5-HT2A receptor agonist;Serotonergic psychedelic;Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Onset of action20–70 minutes[1]
Duration of action10–40 hours[1]
Identifiers
  • 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan-1-one
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC10H12BrNO3
Molar mass274.111 g/mol (freebase)
310.572 g/mol (HCl salt) g·mol−1
3D model (JSmol)
  • COC1=CC(C(=O)CN)=C(OC)C=C1Br
  • InChI=1S/C10H12BrNO3/c1-14-9-4-7(11)10(15-2)3-6(9)8(13)5-12/h3-4H,5,12H2,1-2H3
  • Key:HFYJGAIOBIDRPX-UHFFFAOYSA-N

βk-2C-B,bk-2C-B, also known as4-bromo-2,5-dimethoxy-β-ketophenethylamine or asβ-keto-2C-B, is apsychedelic drug of thephenethylamine and2C family.[2][1] It is the β-ketoderivative of2C-B.[2][1] The drug is takenorally.[1]

The drug acts as a very-low-potencyserotonin5-HT2A receptoragonist.[3][4]

βk-2C-B was first described in thescientific literature byRichard Glennon and colleagues in 2004.[5] It was first encountered as a noveldesigner drug inEurope in 2013.[6][2][1] The drug has since become acontrolled substance inCanada,Germany,Switzerland, and theUnited Kingdom.[citation needed]

Use and effects

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βk-2C-B was not included nor mentioned inAlexander Shulgin's bookPiHKAL (Phenethylamines I Have Known and Loved).[7] However, it subsequently emerged as a novelrecreationaldesigner drug and its properties and effects were reported.[1] βk-2C-B is usually takenorally, but may also be used by otherroutes.[1]Insufflation is said to be not well-tolerated.[1] The drug has been said to be used at doses of 150 to 1,000 mg orally.[1] Itsonset is said to be 20 to 70 minutes and itsduration is said to long at 10 to 40 hours.[1] The effects of βk-2C-B have been said to includeeuphoria,psychedelic visuals,entactogenic effects, and sensory enhancement, among others.[1]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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βk-2C-B acts as a very-low-potencyserotonin5-HT2A receptorpartial agonist.[3][4] ItsEC50Tooltip half-maximal effective concentration was found to be 905 nM and itsEmaxTooltip maximal efficacy was 41%.[3] For comparison, 2C-B had anEC50 of 9.0 nM and anEmax of 89% in the same study.[3] In another study, βk-2C-B'sEC50 at the serotonin 5-HT2A receptor was 6,732 nM, compared to 0.28 nM in the case of2C-I and 0.78 nM in the case of2C-E (2C-B was not reported).[4]

The interactions of βk-2C-B withmonoamine oxidase (MAO) enzymes have been studied.[8] Weak inhibition caused by βk-2C-B is evident at anIC50Tooltip half-maximal inhibitory concentration of 14,000 nM forMAO-B whereas forMAO-A inhibition was undetectable.[8]

Chemistry

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βk-2C-B, also known as 4-bromo-2,5-dimethoxy-β-ketophenethylamine, is asubstituted phenethylamine of the2C family.[1] It is the β-ketoderivative of2C-B.[1]

Synthesis

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Thechemical synthesis of βk-2C-B has been described.[5]

Decomposition

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The thermal decomposition of βk-2C-B has been studied using a simulated 'meth pipe' scenario.[9] Twelve major pyrolysis products were found for the thermally-induced decomposition of βk-2C-B.[9]

Analogues

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Analogues of βk-2C-B include2C-B,β-methyl-2C-B (BMB),BOB (β-methoxy-2C-B), andBOH-2C-B (BOHB; β-hydroxy-2C-B), among others.[7]

History

[edit]

βk-2C-B was first described in thescientific literature byRichard Glennon and colleagues in 2004.[5] It was first encountered as a noveldesigner drug inEurope in 2013.[6][2][1] In the years after its emergence on the market, papers reporting analytical characterizations of the substance appeared.[2][10] In October 2016, βk-2C-B has become acontrolled substance inCanada.[11] It is also became illegal inGermany,Switzerland, and theUnited Kingdom.[citation needed]

Society and culture

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Legal status

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βk-2C-B is acontrolled substance in the following countries:

  • Canada: βk-2C-B is a Schedule III controlled substance as of October 12, 2016.[11]
  • Germany: βk-2C-B is controlled under the New Psychoactive Substances Act (NpSG) as of November 26, 2016. Possession is illegal but not penalized.[citation needed]
  • Sweden: βk-2C-B was classified as a narcotic on April 5, 2019.[12]
  • Switzerland: βk-2C-B is a controlled substance specifically named under Verzeichnis E.,[13]
  • United Kingdom: βk-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.[14]
  • United States: βk-2C-B is unscheduled in the U.S., but may be considered an analogue of 2C-B under the Federal Analogue Act, and thus a Schedule I drug.[citation needed]

See also

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References

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  1. ^abcdefghijklmnop"Bk-2C-B"(PDF).aklagare.se [The Swedish Prosecution Authority] (in Swedish).
  2. ^abcdePower JD, Kavanagh P, O'Brien J, Barry M, Twamley B, Talbot B, et al. (June 2015). "Test purchase, identification and synthesis of 2-amino-1-(4-bromo-2, 5-dimethoxyphenyl)ethan-1-one (bk-2C-B)".Drug Testing and Analysis.7 (6):512–518.doi:10.1002/dta.1699.PMID 25078895.
  3. ^abcdPottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor".Archives of Toxicology.94 (10):3449–3460.Bibcode:2020ArTox..94.3449P.doi:10.1007/s00204-020-02836-w.hdl:1854/LU-8687071.PMID 32627074.S2CID 220337019.
  4. ^abcÅstrand A, Guerrieri D, Vikingsson S, Kronstrand R, Green H (December 2020)."In vitro characterization of new psychoactive substances at the μ-opioid, CB1, 5HT1A, and 5-HT2A receptors-On-target receptor potency and efficacy, and off-target effects".Forensic Science International.317 110553.doi:10.1016/j.forsciint.2020.110553.PMID 33160102.
  5. ^abcGlennon RA, Bondarev ML, Khorana N, Young R, May JA, Hellberg MR, McLaughlin MA, Sharif NA (November 2004). "Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane".J Med Chem.47 (24):6034–6041.doi:10.1021/jm040082s.PMID 15537358.
  6. ^abhttps://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013
  7. ^abShulgin, Alexander;Shulgin, Ann (September 1991).PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press.ISBN 0-9630096-0-5.OCLC 25627628.
  8. ^abWagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases".Drug Testing and Analysis.11 (2):318–324.doi:10.1002/dta.2494.PMID 30188017.S2CID 52166076.
  9. ^abTexter KB, Waymach R, Kavanagh PV, O'Brien JE, Talbot B, Brandt SD, Gardner EA (January 2018)."Identification of pyrolysis products of the new psychoactive substance 2-amino-1-(4-bromo-2,5-dimethoxyphenyl)ethanone hydrochloride (bk-2C-B) and its iodo analogue bk-2C-I".Drug Testing and Analysis.10 (1):229–236.doi:10.1002/dta.2200.PMID 28371351.
  10. ^Frison G, Odoardi S, Frasson S, Sciarrone R, Ortar G, Romolo FS, Strano Rossi S (July 2015). "Characterization of the designer drug bk-2C-B (2-amino-1-(bromo-dimethoxyphenyl)ethan-1-one) by gas chromatography/mass spectrometry without and with derivatization with 2,2,2-trichloroethyl chloroformate, liquid chromatography/high-resolution mass spectrometry, and nuclear magnetic resonance".Rapid Communications in Mass Spectrometry.29 (13):1196–1204.doi:10.1002/rcm.7211.PMID 26395784.
  11. ^ab"Canada Gazette – Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)".Public Works and Government Services Canada. Government of Canada. 2016-05-04. Retrieved2021-08-07.
  12. ^"Åtta nya ämnen klassas som narkotika" [Eight new substances are classified as narcotics].Folkhälsomyndigheten [The Swedish Public Health Agency] (in Swedish). 5 April 2019.På förslag av Folkhälsomyndigheten har regeringen beslutat att klassificera ytterligare åtta ämnen som narkotika från och med den 5 april 2019. [On a proposal from the Swedish Public Health Agency, the government has decided to classify eight more substances as narcotics as of 5 April 2019.]
  13. ^"Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" [Ordinance of the EDI on the registers of narcotics, psychotropic substances, precursors and auxiliary chemicals].Das Eidgenössische Departement des Innern (EDI) [Confederate Department of the Interior] (in German). Der Bundesrat Schweiz.
  14. ^"Psychoactive Substances Act 2016". U.K. Home Office. 28 January 2016. Retrieved8 September 2016.

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