N-Methyl-2C-B

Pharmaceutical compound From Wikipedia, the free encyclopedia

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]

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

Legal status

In general Unscheduled

Quick facts Clinical data, Other names ...

N-Methyl-2C-B
Clinical data

Other names	N-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
IUPAC name 2-(4-bromo-2,5-dimethoxyphenyl)-N-methylethanamine
CAS Number	155639-22-8^Y
PubChem CID	9970546
ChemSpider	8146138
UNII	X5VFU3X44E
ChEMBL	ChEMBL57000
Chemical and physical data
Formula	C₁₁H₁₆BrNO₂
Molar mass	274.158 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CNCCC1=CC(=C(C=C1OC)Br)OC
InChI 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

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-HT_2A and 5-HT_2C receptors.^[3]^[2] Its affinities (K_i) were 2.9 nM for the DOI-labeled serotonin 5-HT_2A receptor, 380 nM for the ketanserin-labeled serotonin 5-HT_2A receptor, and 100 nM for the serotonin 5-HT_2C 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

Legal status

Canada

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

References

[1]
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]
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]
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.

N-Methyl-2C-B

Use and effects

Pharmacology

Pharmacodynamics

History

Society and culture

Legal status

Canada

See also

References

External links

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