Chemistry:2C-B-BUTTERFLY

2C-B-BUTTERFLY
Clinical data
ATC code	none;
Legal status
Legal status	In general Uncontrolled;
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;
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;

Short description: Chemical compound

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-HT_2C over 5-HT_2A.^[2]^[3]

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-NB:

Substituted benzofurans:

2C-B-FLY
2CBFly-NBOMe (NBOMe-2CB-Fly)

Other:

Legal Status

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

References

↑ "Synthesis of hexahydrobenzodipyrans as ring-expanded analogues of potent serotonin 5-HT2A/2C receptor probes.". UW-LaCrosseJUR 2: 61–68. 1999.
↑ "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry 10 (10): 3301–6. October 2002. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876.
↑ "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry 16 (11): 6242–51. June 2008. doi:10.1016/j.bmc.2008.04.030. PMID 18467103.
↑ "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.

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

[2] "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry 10 (10): 3301–6. October 2002. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876.

[3] "'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines". Bioorganic & Medicinal Chemistry 16 (11): 6242–51. June 2008. doi:10.1016/j.bmc.2008.04.030. PMID 18467103.

[4] "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.

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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-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V 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 Methylphenidate 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 (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA 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 N-Ethylhexedrone N-Ethylpentedrone 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) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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Clinical data

ATC code	none
Legal status
Legal status	In general Uncontrolled
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
UNII	32KDF24W6P
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

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