2CBFly-NBOMe

2CBFly-NBOMe
Clinical data
Other names	2C-B-FLY-NBOMe; NBOMe-2C-B-FLY; Cimbi-31; N-(2-Methoxybenzyl)-2C-B-FLY
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None;
Identifiers
	IUPAC name 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b′]difuran-4-yl)-N-[(2-methoxyphenyl)methyl]ethan-1-amine;
CAS Number	1335331-42-4 Y[chemspider];
PubChem CID	57469208;
ChemSpider	26234936 Y;
UNII	Q7PG4YH2H4;
CompTox Dashboard (EPA)	DTXSID40726752 ;
Chemical and physical data
Formula	C20H22BrNO3
Molar mass	404.304 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1ccccc1CNCCc1c2CCOc2c(Br)c2CCOc12;
	InChI InChI=1S/C20H22BrNO3/c1-23-17-5-3-2-4-13(17)12-22-9-6-14-15-7-10-25-20(15)18(21)16-8-11-24-19(14)16/h2-5,22H,6-12H2,1H3 Y; Key:CUFCITSPWAZWHS-UHFFFAOYSA-N Y;
	NY (what is this?) (verify)

Pharmaceutical compound

2CBFly-NBOMe, also known as NBOMe-2C-B-FLY or as Cimbi-31, is a serotonin receptor modulator of the phenethylamine, DOx, and FLY families. It was indirectly derived from the phenethylamine hallucinogen 2C-B is and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25B-NBOMe.

Interactions

Pharmacology

Pharmacodynamics

2CBFly-NBOMe acts as a potent partial agonist for the 5-HT_2A serotonin receptor subtype.^[1]^[2]^[3]

Chemistry

Analogues

Analogues of 2CBFly-NBOMe include 2C-B-FLY and 25B-NBOMe, among others.

History

2CBFly-NBOMe was discovered in 2002,^[4] and further researched by Ralf Heim at the Free University of Berlin,^[5] and subsequently investigated in more detail by a team at Purdue University led by David E. Nichols.^[6]

Society and culture

Legal status

2CBFly-NBOMe is a controlled substance in Canada under phenethylamine blanket-ban language.^[7]

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.^[8]

United States

2CBFly-NBOMe is not an explicitly controlled substance in the United States.^[9] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

2CBFly-NBOMe is a controlled substance in Vermont as of January 2016.^[10]

References

↑ Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.
↑ Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.
↑ Hansen M (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen. Archived from the original on 2013-10-22. Retrieved 2012-11-02.
↑ Elz S, Klass T, Heim R, Warnke U, Pertz HH (2002). "Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function". Naunyn-Schmiedeberg's Archives of Pharmacology. 365 (1 Suppl): R21–R40. doi:10.1007/s00210-002-0604-4.
↑ Heim R (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Free University of Berlin.
↑
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
↑ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
↑ "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.

External links

[pmid21088982-1] Silva ME, Heim R, Strasser A, Elz S, Dove S (January 2011). "Theoretical studies on the interaction of partial agonists with the 5-HT2A receptor". Journal of Computer-Aided Molecular Design. 25 (1): 51–66. Bibcode:2011JCAMD..25...51S. CiteSeerX 10.1.1.688.2670. doi:10.1007/s10822-010-9400-2. PMID 21088982. S2CID 3103050.

[2] Ettrup A, Hansen M, Santini MA, Paine J, Gillings N, Palner M, et al. (April 2011). "Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers". European Journal of Nuclear Medicine and Molecular Imaging. 38 (4): 681–93. doi:10.1007/s00259-010-1686-8. PMID 21174090. S2CID 12467684.

[3] Hansen M (2011). Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain (PhD.). University of Copenhagen. Archived from the original on 2013-10-22. Retrieved 2012-11-02.

[4] Elz S, Klass T, Heim R, Warnke U, Pertz HH (2002). "Development of highly potent partial agonists and chiral antagonists as tools for the study of 5-HT2A-receptor mediated function". Naunyn-Schmiedeberg's Archives of Pharmacology. 365 (1 Suppl): R21–R40. doi:10.1007/s00210-002-0604-4.

[5] Heim R (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Free University of Berlin.

[6] ↑

[CDSA-7] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

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

[OrangeBook2026-9] Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

[10] "Regulated Drugs Rule" (PDF). Vermont Department of Health. Archived from the original (PDF) on 5 June 2016. Retrieved 14 October 2015.

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