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βk-2C-B

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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
PubChem CID
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 as 4-bromo-2,5-dimethoxy-β-ketophenethylamine or as β-keto-2C-B, is a psychedelic drug of the phenethylamine and 2C family.[2][1] It is the β-keto derivative of 2C-B.[2][1] The drug is taken orally.[1]

The drug acts as a very-low-potency serotonin 5-HT2A receptor agonist.[3][4]

βk-2C-B was first described in the scientific literature by Richard Glennon and colleagues in 2004.[5] It was first encountered as a novel designer drug in Europe in 2013.[6][2][1] The drug has since become a controlled substance in Canada, Germany, Switzerland, and the United Kingdom.[citation needed]

Use and effects

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βk-2C-B was not included or mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[7] However, it subsequently emerged as a novel recreational designer drug and its properties and effects were reported.[1] βk-2C-B is usually taken orally, but may also be used by other routes.[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] Its onset is said to be 20 to 70 minutes and its duration is said to long at 10 to 40 hours.[1] The effects of βk-2C-B have been said to include euphoria, psychedelic visuals, entactogenic effects, and sensory enhancement, among others.[1]

Interactions

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

Pharmacology

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Pharmacodynamics

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βk-2C-B acts as a very-low-potency serotonin 5-HT2A receptor partial agonist.[3][4] Its EC50Tooltip half-maximal effective concentration was found to be 905 nM and its EmaxTooltip maximal efficacy was 41%.[3] For comparison, 2C-B had an EC50 of 9.0 nM and an Emax of 89% in the same study.[3] In another study, βk-2C-B's EC50 at the serotonin 5-HT2A receptor was 6,732 nM, compared to 0.28 nM in the case of 2C-I and 0.78 nM in the case of 2C-E (2C-B was not reported).[4]

The interactions of βk-2C-B with monoamine oxidase (MAO) enzymes have been studied.[8] Weak inhibition caused by βk-2C-B is evident at an IC50Tooltip half-maximal inhibitory concentration of 14,000 nM for MAO-B whereas for MAO-A inhibition was undetectable.[8]

Chemistry

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βk-2C-B, also known as 4-bromo-2,5-dimethoxy-β-ketophenethylamine, is a substituted phenethylamine of the 2C family.[1] It is the β-keto derivative of 2C-B.[1]

Synthesis

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The chemical 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 include 2C-B, β-methyl-2C-B (BMB), BOB (β-methoxy-2C-B), and BOH-2C-B (BOHB; β-hydroxy-2C-B), among others.[7]

History

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βk-2C-B was first described in the scientific literature by Richard Glennon and colleagues in 2004.[5] It was first encountered as a novel designer drug in Europe 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 a controlled substance in Canada.[11] It is also became illegal in Germany, Switzerland, and the United Kingdom.[citation needed]

Society and culture

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βk-2C-B is a controlled 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. ^ a b c d e f g h i j k l m n o p "Bk-2C-B" (PDF). aklagare.se [The Swedish Prosecution Authority] (in Swedish).
  2. ^ a b c d e Power 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. ^ a b c d Pottie 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. ^ a b c Åstrand 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. ^ a b c Glennon 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. ^ a b https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2013
  7. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  8. ^ a b Wagmann 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. ^ a b Texter 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. ^ a b "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. Retrieved 2021-08-07.
  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. Retrieved 8 September 2016.
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