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N-Methyl-2C-B

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N-Methyl-2C-B
Clinical data
Other namesN-Me-2C-B; 2C-B-M; 2C-BM; 4-Bromo-2,5-dimethoxy-N-methylphenethylamine; 2,5-Dimethoxy-4-bromo-N-methylphenethylamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(4-bromo-2,5-dimethoxyphenyl)-N-methylethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H16BrNO2
Molar mass274.158 g·mol−1
3D model (JSmol)
  • CNCCC1=CC(=C(C=C1OC)Br)OC
  • InChI=1S/C11H16BrNO2/c1-13-5-4-8-6-11(15-3)9(12)7-10(8)14-2/h6-7,13H,4-5H2,1-3H3
  • Key:ZRTYZUYYGULHEW-UHFFFAOYSA-N

N-Methyl-2C-B, or N-Me-2C-B, also known as 2C-B-M or 2C-BM, as well as 4-bromo-2,5-dimethoxy-N-methylphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families.[1][2][3] It is the N-methyl derivative of 2C-B.[1][2][3]

Pharmacology

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The drug showed affinity for the serotonin 5-HT2 receptors, specifically for the serotonin 5-HT2A and 5-HT2C receptors.[3][2] Its affinities (Ki) were 2.9 nM for the DOI-labeled serotonin 5-HT2A receptor, 380 nM for the ketanserin-labeled serotonin 5-HT2A receptor, and 100 nM for the serotonin 5-HT2C receptor.[3][2] These affinities were approximately 3-fold, 11-fold, and 3-fold lower than those of 2C-B, respectively.[3][2]

2C-B has been tested in humans by P. Rausch and was reported to be completely inactive.[1][4]

History

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N-Methyl-2C-B was first described in the scientific literature by Richard Glennon and colleagues by 1994.[3] It was encountered as a novel designer drug in Europe in 2014.[5]

See also

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References

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  1. ^ a b c Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 834–835, 878. ISBN 978-3-03788-700-4. OCLC 858805226. 8.5.26. N-Substitution von 2,4,5-trisubstituierten Phenylalkylaminen: Einerseits wurde der Einfluss von N-Alkyl-, andererseits derjenige von N-Heterogruppen-Substituenten geprüft. Allgemein ist bekannt, dass das Einführen von Alkylsubstituenten am Stickstoff von psychedelischen Phenylalkylaminen eine Abnahme der HT2-Rezeptoraffinitäten zur Folge hat [29, 150, 151]. Die Wirkungsabschwächung konnte mit den potenten Substanzen DOB (2) und DOM (8) im Menschen bestätigt werden [8]: N-Methyl-DOM (316; BEATRICE) und METHYL-DOB (317) erwiesen sich im Vergleich zu den beiden unmethylierten Verbindungen als massiv weniger aktiv; die aktive Dosis wurde dabei noch nicht eruiert. METHYL-DOET (318; DOETM) erwies sich bei einer Dosierung von 18mg bereits als deutlich aktiv [140]; die Wirkungen wurden im Vergleich zu DOET (14) als ruhiger und angenehmer beschrieben. [...] 318; METHYL-DOET, 18mg, 8-10h. [...] Die N-Methylierung von 2C-B (6) ergab eine im Menschen völlig wirkungslose Substanz (2C-BM; 319) [145]. [...] [140] P. Rausch. Persönliche Mitteilung, 2009. [...] [145] P. Rausch. Yearbook of the European College for the Study of Consciousness. Aglaster, Amand: 1995.
  2. ^ a b c d e Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chemical Reviews. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123. From the results of the binding affinity study, it was found that the 4-substituted derivatives displayed dramatically increased binding affinity at the 5-HT2AR than the unsubstituted (77, 2C-H) analogues, and halogen substitution might be preferred. Among them, compounds 79 (2C-B) and 80 (2C-I) were reported to show the highest binding affinity at h5-HT2AR (Ki = 8.6 nM and 3.5 nM, respectively, [ 3 H]- ketanserin) and favorable functional potency (EC50 = 80 nM and 60 nM, respectively).168 [...] For the phenethylamines, the primary amine could be substituted with small alkyl groups, for example, compounds 138 and 139 (Ki = 2.9 and 16 nM, respectively; [ 125I]-DOI) (Figure 13A).126
  3. ^ a b c d e f Glennon RA, Dukat M, el-Bermawy M, Law H, De los Angeles J, Teitler M, et al. (June 1994). "Influence of amine substituents on 5-HT2A versus 5-HT2C binding of phenylalkyl- and indolylalkylamines". Journal of Medicinal Chemistry. 37 (13): 1929–1935. doi:10.1021/jm00039a004. PMID 8027974.
  4. ^ Rausch P (1995). "Jahrbuch des Europäischen Collegiums für Bewusstseinsstudien" [Yearbook of the European College for the Study of Consciousness]. Berlin: VWB. ISSN 0942-7600.
  5. ^ EMCDDA-Europol 2014 Annual Report on the implementation of Council Decision 2005/387/JHA (PDF) (Report). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) and European Union Agency for Law Enforcement Cooperation (Europol). Archived from the original (PDF) on 15 July 2024.
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