2C-B-BUTTERFLY

2C-B-BUTTERFLY
Clinical data
ATC code	none;
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 (2C-B-MOTH, 2C-B-BFLY) is a conformationally-restricted derivative of the hallucinogen 2C-B and a member of the phenethylamine, 2C, and FLY families. It 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-HT_2C over 5-HT_2A.^[2]^[3]

^ 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.
^ 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.
^ 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.

[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.

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