Chemistry:2C-B-ButterFLY

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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-HT2C over 5-HT2A.[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

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.

See also

  • FLY (psychedelics)
  • 2C-D-5-EtO

References

  1. ↑ 1.0 1.1 "Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes.". UW-LaCrosseJUR 2: 61–68. 1999. 
  2. ↑ 2.0 2.1 2.2 2.3 "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry 10 (10): 3301–3306. October 2002. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876. 
  3. ↑ 3.0 3.1 3.2 "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry 16 (11): 6242–6251. June 2008. doi:10.1016/j.bmc.2008.04.030. PMID 18467103. 
  4. ↑ 4.0 4.1 Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0. 
  5. ↑ 5.0 5.1 Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013) (in de). Phenethylamine: von der Struktur zur Funktion. Nachtschatten-Science (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. https://books.google.com/books?id=-Us1kgEACAAJ. 
  6. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  7. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Methodological Guidelines for the Application of Annex 1 to the Cabinet Regulation No. 847. Ministry of Health of the Republic of Latvia. 8 November 2005. http://www.vm.gov.lv/images/userfiles/metodiskas_vadlinijas_080914.doc. 
  8. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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