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 ;
Chemical and physical data
Formula	C14H18BrNO2
Molar mass	312.202 g/mol
3D model (Jmol)	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 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-HT_2C over 5-HT_2A.^[2]^[3]

Legal Status[edit]

2C-B-BUTTERFLY is illegal in Latvia.^[4]

References[edit]

^ Whiteside, MS. Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes. UW-LaCrosseJUR, 1999; 2: 61–68.
^ Whiteside MS, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE, Monte A. Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes. Bioorg. Med. Chem 2002; 10(10): 3301–3306. doi: 10.1016/S0968-0896(02)00209-2
^ Schultz DM, Prescher JA, Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem 2008; 16(11): 6242–6251. doi: 10.1016/j.bmc.2008.04.030
^ Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem

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[1] Whiteside, MS. Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes. UW-LaCrosseJUR, 1999; 2: 61–68.

[2] Whiteside MS, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE, Monte A. Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes. Bioorg. Med. Chem 2002; 10(10): 3301–3306. doi: 10.1016/S0968-0896(02)00209-2

[3] Schultz DM, Prescher JA, Kidd, S; Marona-Lewicka, D; Nichols, DE; Monte, A. ‘Hybrid’ benzofuran–benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. Bioorg. Med. Chem 2008; 16(11): 6242–6251. doi: 10.1016/j.bmc.2008.04.030

[4] Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem

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v t e Phenethylamines

Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-B-FLY βk-2C-B 2C-C 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-I 2C-N 2C-P 2C-SE 2C-T 2C-T-2 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-21 2C-TFM 2C-YN Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA

Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA MDEA MDHMA MDMA MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DFMDA Selegiline (also D -Deprenyl)

Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine

Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone

Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine

Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone

Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine

Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Theodrenaline Thiamphenicol UWA-101

2C-B-BUTTERFLY

Legal Status[edit]

See also[edit]

References[edit]

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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^N
PubChem CID	10244981
ChemSpider	8420468^Y
Chemical and physical data
Formula	C₁₄H₁₈BrNO₂
Molar mass	312.202 g/mol
3D model (Jmol)	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