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;
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 ; Key:CLSBQRBXTFTLEX-ZDUSSCGKSA-N ;
	(what is this?) (verify)

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 0.27 nM 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:

25-NB:

25-NM:

Substituted benzofurans:

2C-B-FLY
- 2C-B-BUTTERFLY
- 2C-B-DRAGONFLY
2CBFly-NBOMe (NBOMe-2CB-Fly)
DOB-FLY
DOB-2-DRAGONFLY-5-BUTTERFLY

N-(2C)-fentanyl:

N-(2C-B) fentanyl^[2]
- N-(2C-B-FLY) fentanyl^[3]

Other:

BOB
BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB^[4]^[5]
BMB
2C-B-5-hemifly
2C-B-aminorex (2C-B-AR)
2C-B-AN
2C-B-BZP
2C-B-FLY-NB2EtO5Cl
2C-B-PP
2CB-Ind
βk-2C-B (beta-keto 2C-B)
N-Ethyl-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.^[6]

United States

2CBCB-NBOMe is a controlled substance in Vermont as of January 2016.^[7]

References

^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D.). Purdue University. ProQuest 304838368.
^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
^ Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
^ "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. Retrieved 14 October 2015.

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

[2] "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.

[3] "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.

[4] Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.

[5] Beta-hydroxyphenylalkylamines and their use for treating glaucoma

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

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

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