2C-B-BUTTERFLY
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general Uncontrolled
Identifiers
  • 2-(10-Bromo-2,3,4,7,8,9-hexahydropyrano[2,3-g]chromen-5-yl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC14H18BrNO2
Molar mass312.207 g·mol−1
3D model (JSmol)
  • O3CCCc1c3c(Br)c2CCCOc2c1CCN
  • 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 (2C-B-MOTH-BIKHIR, 2C-B-BFLY) is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte.[1] It is a ring-expanded homologue of the better known compound 2C-B-FLY, and has similar properties as an agonist for serotonin receptors, but with more selectivity for 5-HT2C over 5-HT2A.[2][3]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

25-NB:

25-NM:

Substituted benzofurans:

N-(2C)-fentanyl:

Other:

Legal Status

2C-B-BUTTERFLY is illegal in Latvia.[8]

See also

References

  1. ^ Whiteside MS (1999). "Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes". UW-LaCrosseJUR. 2: 61–68. CiteSeerX 10.1.1.688.4722.
  2. ^ 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): 3301–6. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876.
  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): 6242–51. doi:10.1016/j.bmc.2008.04.030. PMC 2601679. PMID 18467103.
  4. ^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
  5. ^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
  6. ^ 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.
  7. ^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
  8. ^ "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.
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