Chemistry:DOB-FLY

DOB-FLY
Legal status
Legal status	UK: In general Uncontrolled ;
Identifiers
	IUPAC name 1-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine;
CAS Number	219986-75-1 ;
PubChem CID	10017554;
ChemSpider	8193127;
UNII	7FBG8DMS2E;
ChEMBL	ChEMBL101008;
Chemical and physical data
Formula	C13H16BrNO2
Molar mass	298.180 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=C2CCOC2=C(C3=C1OCC3)Br)N;
	InChI InChI=1S/C13H16BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h7H,2-6,15H2,1H3; Key:FKRREVSELFOLDT-UHFFFAOYSA-N;

Short description: Psychedelic designer drug

DOB-FLY is a recreational designer drug with psychedelic effects. It can be regarded as the alpha-methyl derivative of 2C-B-FLY or the partially saturated counterpart of bromo-dragonfly. Unlike bromo-dragonfly, DOB-FLY is only slightly more potent than DOB itself, with an active dose in humans of around 1 mg.^[1]^[2]^[3]^[4]^[5]^[6]

References

↑ "A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor". Journal of Medicinal Chemistry 41 (26): 5148–9. December 1998. doi:10.1021/jm9803525. PMID 9857084.
↑ "Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity". Bioorganic & Medicinal Chemistry Letters 17 (11): 2998–3002. June 2007. doi:10.1016/j.bmcl.2007.03.073. PMID 17419053.
↑ "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry 16 (8): 4661–9. April 2008. doi:10.1016/j.bmc.2008.02.033. PMID 18296055.
↑ "'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.
↑ "Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl) aminoalkanes (FLYs) and (benzodifuranyl) aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS.". Forensic Toxicology 28 (1): 9–18. January 2010. doi:10.1007/s11419-009-0083-0.
↑ "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology 144: 368–376. January 2019. doi:10.1016/j.neuropharm.2018.10.037. PMID 30385253.

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[1] "A novel (benzodifuranyl)aminoalkane with extremely potent activity at the 5-HT2A receptor". Journal of Medicinal Chemistry 41 (26): 5148–9. December 1998. doi:10.1021/jm9803525. PMID 9857084.

[2] "Novel benzodifuran analogs as potent 5-HT2A receptor agonists with ocular hypotensive activity". Bioorganic & Medicinal Chemistry Letters 17 (11): 2998–3002. June 2007. doi:10.1016/j.bmcl.2007.03.073. PMID 17419053.

[3] "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry 16 (8): 4661–9. April 2008. doi:10.1016/j.bmc.2008.02.033. PMID 18296055.

[4] "'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.

[5] "Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl) aminoalkanes (FLYs) and (benzodifuranyl) aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS.". Forensic Toxicology 28 (1): 9–18. January 2010. doi:10.1007/s11419-009-0083-0.

[6] "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology 144: 368–376. January 2019. doi:10.1016/j.neuropharm.2018.10.037. PMID 30385253.

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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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Legal status

Legal status	UK: In general Uncontrolled
Identifiers
IUPAC name 1-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine
CAS Number	219986-75-1^Y
PubChem CID	10017554
ChemSpider	8193127
UNII	7FBG8DMS2E
ChEMBL	ChEMBL101008
Chemical and physical data
Formula	C₁₃H₁₆BrNO₂
Molar mass	298.180 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(CC1=C2CCOC2=C(C3=C1OCC3)Br)N
InChI InChI=1S/C13H16BrNO2/c1-7(15)6-10-8-2-4-17-13(8)11(14)9-3-5-16-12(9)10/h7H,2-6,15H2,1H3 Key:FKRREVSELFOLDT-UHFFFAOYSA-N

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