DOx

DOx
2,5-Dimethoxyamphetamine (2,5-DMA), the base structure of the DOx family.

DOx is a term used to refer to a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkyl or halogen at the 4- position of the phenyl ring. The compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonists.

The DOx family includes the following members:

Structure Name Abbreviation
DOAM.png 2,5-Dimethoxy-4-amylamphetamine DOAM
DOB.svg 2,5-Dimethoxy-4-bromoamphetamine DOB
DOBU.png 2,5-Dimethoxy-4-butylamphetamine DOBU
DOC.svg 2,5-Dimethoxy-4-chloroamphetamine DOC
MEM.png 2,5-Dimethoxy-4-ethoxyamphetamine MEM
2,5-Dimethoxy-4-ethylamphetamine.svg 2,5-Dimethoxy-4-ethylamphetamine DOET
2,5-dimethoxy-4-ethylthioamphetamine.svg 2,5-Dimethoxy-4-ethylthioamphetamine Aleph-2
2,5-Dimethoxy-4-fluoroamphetamine.svg 2,5-Dimethoxy-4-fluoroamphetamine DOF
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine.svg 2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine DOEF
DOI.svg 2,5-Dimethoxy-4-iodoamphetamine DOI
Aleph-4.svg 2,5-Dimethoxy-4-isopropylthioamphetamine Aleph-4
Trimethoxyamphetamine-2.svg 2,4,5-Trimethoxyamphetamine TMA-2
2,5-Dimethoxy-4-methylamphetamine.svg 2,5-Dimethoxy-4-methylamphetamine DOM
2,5-dimethoxy-4-methylthioamphetamine.svg 2,5-Dimethoxy-4-methylthioamphetamine Aleph-1
2,5-Dimethoxy-4-nitroamphetamine.svg 2,5-Dimethoxy-4-nitroamphetamine DON
Aleph-6.svg 2,5-Dimethoxy-4-phenylthioamphetamine Aleph-6
2,5-Dimethoxy-4-propylamphetamine.svg 2,5-Dimethoxy-4-propylamphetamine DOPR
2,5-dimethoxy-4-propylthioamphetamine.svg 2,5-Dimethoxy-4-propylthioamphetamine Aleph-7
2,5-Dimethoxy-4-trifluoromethylamphetamine.svg 2,5-Dimethoxy-4-trifluoromethylamphetamine DOTFM

As well as the following members with additional substitutions:

See also

References

External links

v · d · eHallucinogens
Psychedelics
5-HT2AR agonists
Lysergamides: AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAM-57 • Diallyllysergamide • Ergometrine (Ergonovine, Ergobasine) • ETH-LAD • LAE-32 • LSA (Ergine, Lysergamide) • LSD • LSH • LPD-824 • LSM-775 • Lysergic Acid 2-Butyl Amide • Lysergic Acid 2,4-Dimethylazetidide • Lysergic Acid 3-Pentyl Amide • Methylergometrine • Methylisopropyllysergamide • Methysergide • MLD-41 • PARGY-LAD • PRO-LAD;
Phenethylamines: Aleph • 2C-B • 2C-B-Dragonfly · 2C-B-FLY • 2C-C-FLY • 2C-D-FLY • 2C-E-FLY • 2C-I-FLY • 2CBFly-NBOMe • 2C-T-7-FLY • 2C-C • 2C-C-NBOMe • 2C-CN-NBOMe • 2C-D • 2CD-5EtO • 2C-D-NBOMe • 2C-E • 2C-EF • 2C-E-NBOMe • 2C-F • 2C-F-NBOMe • 2C-G • 2C-G-NBOMe • 2C-H-NBOMe • 2C-I • 2C-N • 2C-N-NBOMe • 2C-O • 2C-O-4 • 2C-P • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-4-NBOMe • 2C-T-7 • 2C-T-7-NBOH • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-TFM-NBOMe • 2C-YN • 2CBCB-NBOMe • 25B-NBOMe • 25I-NBMD • 25I-NBOH • 25I-NBOMe • 3C-E • 3C-P • 5-APB • 5-APDB • 6-APB • 6-APDB • Br-DFLY • DESOXY • DMMDA • DMMDA-2 • DOB • DOB-FLY • DOM-FLY • DOC • DOEF • DOET • DOF • DOI • DOM • DON • DOPR • DOTFM • Escaline • Ganesha • HOT-2 • HOT-7 • HOT-17 • IAP • Isoproscaline • Jimscaline • Lophophine • MDA • MDEA • MDMA • MMA • MMDA • MMDA-2 • MMDA-3a • MMDMA • Macromerine • Mescaline • Methallylescaline • NBOMe-mescaline • Proscaline • TCB-2 • TFMFly • TMA;
Piperazines: pFPP • TMFPP;
Tryptamines: 1-Methyl-5-methoxy-diisopropyltryptamine • 2,N,N-TMT • 4-HO-5-MeO-DMT • 4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-Acetoxy-DPT • 4-Acetoxy-MiPT • 4-HO-DPT • 4-HO-MET • 4-Propionyloxy-DMT • 4-HO-MPMI • 5-Me-MIPT • 5-N,N-TMT • 5-AcO-DMT • 5-MeO-2,N,N-TMT • 5-MeO-α,N,N-TMT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-EiPT • 5-MeO-MET • 5-MeO-MIPT • 5-MeO-MPMI • 7,N,N-TMT • α,N,N-TMT • α-ET • α-MT • AL-37350A • Baeocystin • Bufotenin • DALT • DBT • DCPT • DET • DIPT • DMT • DPT • EiPT • Ethocin • Ethocybin • Iprocin • MET • Miprocin • MIPT • Norbaeocystin • PiPT • Psilocin • Psilocybin;
Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
3-Quinuclidinyl benzilate • Atropine • Benactyzine • Benzatropine • Benzydamine • Biperiden • Brompheniramine • CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • Chlorpheniramine • Chloropyramine • Clemastine • CS-27349 • Cyclizine • Cyproheptadine • Dicyclomine (Dicycloverine) • Dimenhydrinate • Diphenhydramine • Ditran • Doxylamine • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Flavoxate • Hydroxyzine • Hyoscyamine • Meclizine • Myristicin • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • Pyrilamine • Orphenadrine • Oxybutynin • Pheniramine • Phenyltoloxamine • Procyclidine • Promethazine • Scopolamine (Hyoscine) • Tolterodine • Trihexyphenidyl • Tripelennamine • Triprolidine • WIN-2299
Miscellaneous
Cannabinoids
CB1R agonists
Cannabinol • CP-47,497 • CP-55,244 • CP-55,940 • DMHP • HU-210 • JWH-018 • JWH-030 • JWH-073 • JWH-081 • JWH-200 • JWH-250 • Nabilone • Nabitan • Nantradol • Parahexyl • THC (Dronabinol) • WIN-55,212-2
Butane • Chloroform • Diethyl Ether (Ether) • Enflurane • Freon • Gasoline (Petrol) • Kerosene (Paraffin) • Propane
2-EMSB • 2-MMSB • Alazocine • Bremazocine • Butorphanol • Cyclazocine • Cyprenorphine • Dextrallorphan • Dezocine • Enadoline • Herkinorin • HZ-2 • Ibogaine • Ketazocine • Metazocine • Nalbuphine • Nalorphine • Noribogaine • Pentazocine • Phenazocine • Salvinorin A • Spiradoline • Tifluadom • U-50,488 • U-69,593
Others
v · d · ePhenethylamines
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 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-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: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
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: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol

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Look at other dictionaries:

  • Dox — may refer to: dox, an ISO/FDIS 639 3 code for Bussa language Dox, a type of Warez Dornier Do X, the German aircraft Direct oximetry Dog fox hybrid, a supposed hybrid between a fox and a dog dox, an Internet slang word for personally identifiable… …   Wikipedia

  • DOX — steht für: Dongara, IATA Code des australischen Flughafens Do X steht für: Dornier Do X, ein Verkehrsflugschiff aus dem Jahr 1929 dox steht für: Bussa (Sprache), ISO 639 3 Code der Sprache Dox ist der Familienname folgender Personen: Georg Dox… …   Deutsch Wikipedia

  • dox|y — dox|y1 «DOK see», noun, plural dox|ies. Informal. an opinion or doctrine, especially in religion or theology: »Orthodoxy is my doxy, heterodoxy is another man s doxy (Bishop William Warburton). ╂[abstracted from orthodoxy, heterodoxy, etc.]… …   Useful english dictionary

  • Dox — Dox, de son vrai nom Jean Verdi Salomon Razakandraina, est un poète malgache né en 1913 et mort en 1978. La majorité de son œuvre est d expression malgache. Portail de la littérature …   Wikipédia en Français

  • dox|ie — «DOK see», noun. = doxy2. (Cf. ↑doxy) …   Useful english dictionary

  • dox|ol|o|gy — «dok SOL uh jee», noun, plural gies. a hymn or statement praising God. Three of the best known doxologies begin: “Glory to God in the highest” (greater doxology), “Glory be to the Father and to the Son and to the Holy Ghost” (lesser doxology),… …   Useful english dictionary

  • -dox — see doxy2 …   Useful english dictionary

  • dox — al·dox·ime; am·i·dox·ime; cla·dox·y·la·ce·ae; cla·dox·y·la·les; cla·dox·y·lon; da·dox·y·lon; dox·ic; dox·og·ra·pher; dox·o·log·i·cal; dox·ol·o·gize; dox·ol·o·gy; dox·yl·a·mine; eu·dox·ian; ham·a·mel·i·dox·y·lon; het·er·o·dox; in·dox·yl; mad·dox;… …   English syllables

  • dox — noun a) Documents, especially information sought by hackers about an individual (address, credit card numbers, etc.). Why is it that, even after DECADES of carping from Jerry Pournelle, software companies STILL dont hire competent professionals… …   Wiktionary

  • Dox-SL — A form of the anticancer drug doxorubicin that may have fewer side effects and work better than doxorubicin. Dox SL is used to treat ovarian cancer, AIDS related Kaposi sarcoma, and multiple myeloma in patients whose disease has not gotten better …   English dictionary of cancer terms

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