2CBCB-NBOMe

2CBCB-NBOMe
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 ;
PubChem CID	57483909;
ChemSpider	26234935 ;
UNII	WGI3S41A26;
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 ; Key:CLSBQRBXTFTLEX-ZDUSSCGKSA-N ;
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2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on the mapping of the specific amino acid residues responsible for ligand binding to the 5HT_2A receptor. 2CBCB-NBOMe acts as a potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, with a Ki of 0.27nM at the human 5-HT_2A receptor, a similar potency to other agonists such as TCB-2, NBOMe-2C-I and Bromo-DragonFLY.[1]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

25B-N1POMe
25B-NAcPip

25-NB:

25B-NB
25B-NB23DM
25B-NB25DM
25B-NB3OMe
25B-NB4OMe
25B-NBF
25B-NBMD
25B-NBOH
25B-NBOMe (NBOMe-2CB)

25-NM:

25B-NMe7BF
25B-NMe7BT
25B-NMe7Box
25B-NMe7DHBF
25B-NMe7Ind
25B-NMe7Indz
25B-NMePyr

Substituted benzofurans:

2C-B-FLY
2CBFly-NBOMe (NBOMe-2CB-Fly)

Other:

2C-B-AN
2C-B-BUTTERFLY
2C-B-DRAGONFLY-NBOH
2C-B-DragonFLY
2C-B-FLY-NB2EtO5Cl
2CB-5-hemifly
2CB-Ind
βk-2C-B (beta-keto 2C-B)
TCB-2 (2C-BCB)

Legality

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.[2]

United States

2CBCB-NBOMe is a controlled substance in Vermont as of January 2016.[3]

References

Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.
"The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.
"Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.

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[1] Braden, Michael Robert (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.

[2] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". www.legislation.gov.uk.

[3] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Retrieved 14 October 2015.