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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. 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:

Structure	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	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	125903-73-3
	2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine	DO3MeOBZ	930836-90-1
	2,5-Dimethoxy-4-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
	2,5-Dimethoxy-4-cyanoamphetamine	DOCN	125903-74-4
	2,5-Dimethoxy-4-ethynylamphetamine	DOYN	633290-70-7

Related compounds

A number of additional compounds are known with alternative substitutions:

Structure	Name	Abbreviation	CAS number
	Dimoxamine ("Ariadne")	4C-D	52842-59-8
	1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine	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-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	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-tetrahydrofurobenzofuran-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, ZC-B

See also

• 2Cs, 25-NB
• Substituted amphetamines
• Substituted benzofurans
• Substituted cathinones
• Substituted methylenedioxyphenethylamines
• Substituted phenethylamines
• Substituted tryptamines
• PiHKAL
• The Shulgin Index

References

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. Trachsel D (August 2003). "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. 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

External links

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

• Chemical classes of psychoactive drugs
• 2,5-Dimethoxyphenethylamines