2C-B-ButterFLY

2C-B-ButterFLY
Clinical data
Other names	2C-B-BUTTERFLY; 2C-B-BFLY; 2C-B-Moth; 2C-B-MOTH; 2C-B-PLY
Drug class	Serotonin receptor modulator
ATC code	None;
Legal status
Legal status	In general unscheduled;
Identifiers
	IUPAC name 2-(10-bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g]chromen-5-yl)ethan-1-amine;
CAS Number	502659-24-7 ;
PubChem CID	10244981;
ChemSpider	8420468 ;
UNII	32KDF24W6P;
CompTox Dashboard (EPA)	DTXSID001032894 ;
Chemical and physical data
Formula	C14H18BrNO2
Molar mass	312.207 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O3CCCc1c3c(Br)c2CCCOc2c1CCN;
	InChI InChI=1S/C14H18BrNO2/c15-12-11-4-2-7-17-13(11)10(5-6-16)9-3-1-8-18-14(9)12/h1-8,16H2; Key:PAFZDNLBBBZEKE-UHFFFAOYSA-N;

2C-B-ButterFLY, also known as 2C-B-BFLY or as 2C-B-MOTH, is a serotonin receptor modulator of the phenethylamine, 2C, and FLY families.^[1]^[2]^[3] It is a conformationally-restricted derivative of the psychedelic drug 2C-B and a ring-expanded homologue of the better-known compound 2C-B-FLY.^[2]^[3]

Use and effects

The properties and effects of 2C-B-ButterFLY in humans do not appear to be known.^[4]^[5]

Pharmacology

Pharmacodynamics

2C-B-ButterFLY has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT_2C over 5-HT_2A.^[2]^[3]

Chemistry

Analogues

Analogues of 2C-B-ButterFLY include 2C-B, 2C-B-FLY, 2C-B-DragonFLY, DOB-FLY, and Bromo-DragonFLY (DOB-DFLY), among others.^[4]^[5]

History

2C-B-ButterFLY was discovered by Michael S. Whiteside and Aaron Monte in 1999.^[1]^[2]

Society and culture

Legal status

Canada

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

Latvia

2C-B-ButterFLY is illegal in Latvia.^[7]

United States

2C-B-ButterFLY is not an explicitly controlled substance in the United States.^[8] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

References

1 2 Whiteside M (1999). "Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes". Journal of Undergraduate Research. 2. University of Wisconsin–La Crosse: 61–68.
1 2 3 4 Whiteside MS, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE, Monte A (October 2002). "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry. 10 (10): 3301–3306. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876.
1 2 3 Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A (June 2008). "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry. 16 (11): 6242–6251. doi:10.1016/j.bmc.2008.04.030. PMC 2601679. PMID 18467103.
1 2 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
1 2 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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations Regarding Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia]. Methodological Guidelines for the Application of Annex 1 to the Cabinet Regulation No. 847 (in Latvian). Ministry of Health of the Republic of Latvia. 8 November 2005. Archived from the original on 4 March 2016. Retrieved 8 October 2015.
↑ 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

External links

2C-B-ButterFLY - Isomer Design

[Whiteside1999-1] 1 2 Whiteside M (1999). "Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes". Journal of Undergraduate Research. 2. University of Wisconsin–La Crosse: 61–68.

[WhitesideKurrasch-OrbaughMarona-Lewicka2002-2] 1 2 3 4 Whiteside MS, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE, Monte A (October 2002). "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry. 10 (10): 3301–3306. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876.

[SchultzPrescherKidd2008-3] 1 2 3 Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A (June 2008). "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry. 16 (11): 6242–6251. doi:10.1016/j.bmc.2008.04.030. PMC 2601679. PMID 18467103.

[ShulginManningDaley2011-4] 1 2 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.

[TrachselLehmannEnzensperger2013-5] 1 2 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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.

[CDSA-6] "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.

[7] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations Regarding Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia]. Methodological Guidelines for the Application of Annex 1 to the Cabinet Regulation No. 847 (in Latvian). Ministry of Health of the Republic of Latvia. 8 November 2005. Archived from the original on 4 March 2016. Retrieved 8 October 2015.

[OrangeBook2026-8] 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

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