N-Methyl-2C-B

Last updated

N-Methyl-2C-B
N-methyl-2CB structure.png
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 class Serotonin receptor modulator
ATC code
  • None
Legal status
Legal status
  • In general Unscheduled
Identifiers
  • 2-(4-bromo-2,5-dimethoxyphenyl)-N-methylethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
Formula C11H16BrNO2
Molar mass 274.158 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]

Contents

Use and effects

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

Pharmacology

Pharmacodynamics

N-Methyl-2C-B 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]

History

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]

Society and culture

Canada

N-Methyl-2C-B is a controlled substance in Canada under phenethylamine blanket-ban language. [6]

See also

References

  1. 1 2 3 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. 1 2 3 4 5 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. 1 2 3 4 5 6 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 (January 1995). Leuner H, Schlichting M, European College for the Study of Consciousness (eds.). Jahrbuch des Europäischen Collegiums für Bewußtseinsstudien: 1995[Yearbook of the European College for the Study of Consciousness: 1995] (in German and English). Vol. 4. Berlin: VWB. ISBN   978-3861354079. ISSN   0942-7600. OCLC   28636362.
  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.
  6. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.


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