βk-2C-B
Chemical compound
From Wikipedia, the free encyclopedia
βk-2C-B, or 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.[3][1][2] It is the β-keto derivative of 2C-B.[3][1] The drug is taken orally.[1][2]
- CA: Schedule III
- DE: NpSG (Industrial and scientific use only)
- UK: Under Psychoactive Substances Act
- Illegal in Sweden and Switzerland
 | |
 | |
| Clinical data | |
|---|---|
| Other names | β-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][2] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Onset of action | 20–70 minutes[1][2] |
| Duration of action | 10–40 hours[1] or 10 hours[2] |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C10H12BrNO3 |
| Molar mass | 274.111 g/mol (freebase) 310.572 g/mol (HCl salt) g·mol−1 |
| 3D model (JSmol) | |
| |
| |
The drug acts as a very-low-potency serotonin 5-HT2A receptor agonist.[4][5]
βk-2C-B was first described in the scientific literature by Richard Glennon and colleagues in 2004.[6] It was first encountered as a novel designer drug in Europe in 2013.[7][3][1] The drug has since become a controlled substance in Canada, Germany, Switzerland, and the United Kingdom.[citation needed]
Use and effects
βk-2C-B was not included nor mentioned in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[8] 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][2] 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 be long at 10 to 40 hours.[1] However, other sources have reported a dose range of 50 to 150 mg or more orally, an onset of 30 minutes, and a duration of 10 hours.[2] The effects of βk-2C-B have been said to include euphoria, psychedelic visuals, entactogenic effects, and sensory enhancement, among others.[1][2]
Interactions
Pharmacology
Pharmacodynamics
βk-2C-B acts as a very-low-potency serotonin 5-HT2A receptor partial agonist.[4][5] Its EC50 was found to be 905 nM and its Emax was 41%.[4] For comparison, 2C-B had an EC50 of 9.0 nM and an Emax of 89% in the same study.[4] 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).[5]
The interactions of βk-2C-B with monoamine oxidase (MAO) enzymes have been studied.[9] Weak inhibition caused by βk-2C-B is evident at an IC50 of 14,000 nM for MAO-B whereas for MAO-A inhibition was undetectable.[9]
Chemistry
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
The chemical synthesis of βk-2C-B has been described.[6]
Decomposition
The thermal decomposition of βk-2C-B has been studied using a simulated 'meth pipe' scenario.[10] Twelve major pyrolysis products were found for the thermally-induced decomposition of βk-2C-B.[10]
Analogues
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.[8]
History
βk-2C-B was first described in the scientific literature by Richard Glennon and colleagues in 2004.[6] It was first encountered as a novel designer drug in Europe in 2013.[7][3][1] In the years after its emergence on the market, papers reporting analytical characterizations of the substance appeared.[3][11] Since October 2016, βk-2C-B has been a controlled substance in Canada.[12] It is also illegal in Germany, Switzerland, and the United Kingdom.[citation needed]
Society and culture
Legal status
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.[12]
- 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.[13]
- Switzerland: βk-2C-B is a controlled substance specifically named under Verzeichnis E.,[14]
- United Kingdom: βk-2C-B is illegal to produce, supply or import under the Psychoactive Substance Act as of May 26, 2016.[15]
- United States: βk-2C-B is unscheduled in the U.S.,[16] but may be considered an analogue of 2C-B under the Federal Analogue Act, and thus a Schedule I drug if intended for human consumption.[citation needed]