Chemistry:DOx

Short description: Class of chemical compounds

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

4-Substituted-2,5-dimethoxyamphetamines (DOx) is 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.^[1] Most compounds of this class are potent and long-lasting psychedelic drugs, and act as highly selective 5-HT_2A, 5-HT_2B, and 5-HT_2C receptor partial agonists. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT₂ receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects.

DOx derivatives

The DOx family includes the following members:

Name	Abbreviation	CAS number
2,5-Dimethoxy-4-amylamphetamine	DOAM	63779-90-8
2,5-Dimethoxy-4-bromoamphetamine	DOB	64638-07-9 (racemate)
2,5-Dimethoxy-4-butylamphetamine	DOBU	63779-89-5
2,5-Dimethoxy-4-chloroamphetamine	DOC	123431-31-2
2,5-Dimethoxy-4-ethoxyamphetamine	MEM	16128-88-4
2,5-Dimethoxy-4-(methoxymethyl)amphetamine	DOMOM ^[2]	260810-10-4
2,5-Dimethoxy-4-(ethoxymethyl)amphetamine	DOMOE	930836-81-0
2,5-Dimethoxy-4-ethylamphetamine	DOET	22004-32-6
2,5-Dimethoxy-4-ethylthioamphetamine	Aleph-2	185562-00-9
2,5-Dimethoxy-4-fluoroamphetamine	DOF	125903-69-7
2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine	DOEF	121649-01-2
2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine	DOPF
2,5-Dimethoxy-4-iodoamphetamine	DOI	42203-78-1
2,5-Dimethoxy-4-isopropylthioamphetamine	Aleph-4	123643-26-5
2,5-Dimethoxy-4-methylamphetamine	DOM	15588-95-1
2,5-Dimethoxy-4-methylthioamphetamine	Aleph-1	61638-07-1
2,5-Dimethoxy-4-nitroamphetamine	DON	67460-68-8
2,5-Dimethoxy-4-phenylthioamphetamine	Aleph-6	952006-44-9
2,5-Dimethoxy-4-benzylamphetamine	DOBZ ^[3]	125903-73-3
2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine	DO3MeOBZ ^[4]	930836-90-1
2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine	DOTHFM	930776-12-8
2,5-Dimethoxy-4-propylamphetamine	DOPR	63779-88-4
2,5-Dimethoxy-4-isopropylamphetamine	DOiP	42306-96-7
2,5-Dimethoxy-4-propylthioamphetamine	Aleph-7	207740-16-7
2,5-Dimethoxy-4-(difluoromethyl)amphetamine	DODFM
2,5-Dimethoxy-4-trifluoromethylamphetamine	DOTFM	159277-07-3
2,5-Dimethoxy-4-(2,2,2-trifluoroethyl)amphetamine	DOTFE ^[5]
2,5-Dimethoxy-4-cyanoamphetamine	DOCN ^[6]	125903-74-4
2,5-Dimethoxy-4-ethynylamphetamine	DOYN ^[7]	633290-70-7

Related compounds

A number of additional compounds are known with alternative substitutions:

Name	Abbreviation	CAS number
Dimoxamine ("Ariadne")	4C-D	52842-59-8
1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine ^[8]	4C-E
1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine	4C-P
1-(2,5-Dimethoxy-4-bromophenyl)butan-2-amine	4C-B	69294-23-1
1-(2,5-Dimethoxy-4-chlorophenyl)butan-2-amine	4C-C	791010-74-7
1-(2,5-Dimethoxy-4-iodophenyl)butan-2-amine	4C-I	758631-75-3
1-(2,5-Dimethoxy-4-nitrophenyl)butan-2-amine	4C-N	775234-58-7
1-[2,5-Dimethoxy-4-(ethylthio)phenyl]butan-2-amine	4C-T-2	850007-13-5
Dimethoxymethamphetamine ("Beatrice")	N-methyl-DOM	92206-37-6
2,5-Dimethoxy-3,4-methylenedioxyamphetamine	DMMDA	15183-13-8
2,5-dimethoxy-3,4-dimethylamphetamine ("Ganesha")	3-methyl-DOM	207740-37-2
2,5-Dimethoxy-3,4-trimethylenylamphetamine	G-3
2,5-Dimethoxy-3,4-tetramethylenylamphetamine	G-4
2,5-Dimethoxy-3,4-norbornylamphetamine	G-5
1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine ^[9]	G-O	774538-38-4
2,5-Dimethoxy-3,4-dichloroamphetamine	DODC	1373918-65-0
IDNNA	IDNNA	67707-78-2
Methyl-DOB	N-methyl-DOB	155638-80-5
2,3,4,5-Tetramethoxyamphetamine	2,3,4,5-Tetramethoxyamphetamine	23693-26-7
1-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)propan-2-amine	DOB-FLY	219986-75-1
Bromo-DragonFLY	DOB-DFLY	502759-67-3
3-(4-bromo-2,5-dimethoxyphenyl)azetidine	Compound 1,^[10] ZC-B

References

↑ Daniel Trachsel; David Lehmann; Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
↑ Harms A, Ulmer E, Kovar K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm., 16 Jun 2003, 336(3): 155–158. doi:10.1002/ardp.200390014
↑ Nelson DL, Lucaites VL, Wainscott DB, Glennon RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 1 Jan 1999, 359(1): 1–6. doi:10.1007/PL00005315
↑ Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007
↑ Trachsel D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4(7-8): 577-590.doi:10.1002/dta.413
↑ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33(3): 1032–1036. doi:10.1021/jm00165a023
↑ "Synthesis of Novel (Phenylalkyl) amines for the Investigation of Structure–Activity Relationships, Part 3: 4‐Ethynyl‐2,5‐dimethoxyphenethylamine (= 4‐Ethynyl‐2, 5‐dimethoxybenzeneethanamine; 2C‐YN).". Helvetica Chimica Acta 86 (8): 2754–9. August 2003. doi:10.1002/hlca.200390224.
↑ Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113
↑ Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856
↑ Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908

External links

PiHKAL ("Phenethylamines I Have Known And Loved") by Alexander "Sasha" Shulgin (1991)
Psychotomimetic Drugs: Structure-Activity Relationships by Alexander "Sasha" Shulgin (1978)

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Original source: https://en.wikipedia.org/wiki/DOx. Read more

[Trachsel-1] Daniel Trachsel; David Lehmann; Christoph Enzensperger (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.

[2] Harms A, Ulmer E, Kovar K. Synthesis and 5-HT2A radioligand receptor binding assays of DOMCl and DOMOM, two novel 5-HT2A receptor ligands. Arch. Pharm., 16 Jun 2003, 336(3): 155–158. doi:10.1002/ardp.200390014

[3] Nelson DL, Lucaites VL, Wainscott DB, Glennon RA. Comparisons of hallucinogenic phenylisopropylamine binding affinities at cloned human 5-HT2A, 5-HT2B and 5-HT2C receptors. N-S. Arch. Pharmacol., 1 Jan 1999, 359(1): 1–6. doi:10.1007/PL00005315

[4] Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007

[5] Trachsel D. Fluorine in psychedelic phenethylamines. Drug Test. Anal., 1 Jul 2012, 4(7-8): 577-590.doi:10.1002/dta.413

[6] Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon, RA. A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors. J. Med. Chem., 1 Mar 1990, 33(3): 1032–1036. doi:10.1021/jm00165a023

[7] "Synthesis of Novel (Phenylalkyl) amines for the Investigation of Structure–Activity Relationships, Part 3: 4‐Ethynyl‐2,5‐dimethoxyphenethylamine (= 4‐Ethynyl‐2, 5‐dimethoxybenzeneethanamine; 2C‐YN).". Helvetica Chimica Acta 86 (8): 2754–9. August 2003. doi:10.1002/hlca.200390224.

[8] Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113

[9] Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856

[10] Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908

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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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