2CBCB-NBOMe

2CBCB-NBOMe
Clinical data
Other names	NBOMe-2CBCB; NBOMe-TCB-2; TCB-2-NBOMe
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine;
CAS Number	1354634-09-5 N;
PubChem CID	57483909;
ChemSpider	26234935 Y;
UNII	WGI3S41A26;
CompTox Dashboard (EPA)	DTXSID501028189 ;
Chemical and physical data
Formula	C19H22BrNO3
Molar mass	392.293 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1ccccc1CNCC3c2c(C3)c(OC)c(Br)cc2OC;
	InChI InChI=1S/C19H22BrNO3/c1-22-16-7-5-4-6-12(16)10-21-11-13-8-14-18(13)17(23-2)9-15(20)19(14)24-3/h4-7,9,13,21H,8,10-11H2,1-3H3/t13-/m0/s1 Y; Key:CLSBQRBXTFTLEX-ZDUSSCGKSA-N Y;
	NY (what is this?) (verify)

Chemical compound

Pharmaceutical compound

2CBCB-NBOMe, or NBOMe-TCB-2, is a serotonin receptor modulator and cyclized phenethylamine.^[1]^[2] It is the NBOMe derivative of the psychedelic drug TCB-2 (2C-BCB).^[1]^[2]

Interactions

Pharmacology

Pharmacodynamics

2CBCB-NBOMe acts as a potent and selective agonist of the serotonin 5-HT_2A and 5-HT_2C receptors, with an affinity (K_i) of 0.27 nM at the human serotonin 5-HT_2A receptor, similar to that of other drugs such as TCB-2, 25I-NBOMe, and Bromo-DragonFLY.^[1]^[2]

History

2CB2CB-NBOMe was first described in the scientific literature by the lab of David E. Nichols and colleagues in 2007.^[1]^[2] It was part of an ongoing research program focused on mapping of the specific amino acid residues responsible for ligand binding to the serotonin 5-HT_2A receptor.^[1]^[2]

Society and culture

Legal status

United Kingdom

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.^[3]

United States

2CBCB-NBOMe is a controlled substance in Vermont as of January 2016.^[4]

References

^ a b c d e Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1st ed.). Solothurn: Nachtschatten-Verlag. p. 861. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
^ a b c d e Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D.). Purdue University. ProQuest 304838368.
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
^ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 23 January 2014. Retrieved 14 October 2015.

External links

2CBCB-NBOMe - Isomer Design

[Trachsel_2013-1] Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1st ed.). Solothurn: Nachtschatten-Verlag. p. 861. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.

[Braden_2007-2] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D.). Purdue University. ProQuest 304838368.

[3] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

[4] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 23 January 2014. Retrieved 14 October 2015.