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-HT2A, 5-HT2B, and 5-HT2C 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[edit]
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 [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[edit]
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 [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 |
See also[edit]
- 2Cs, 25-NB
- Substituted amphetamines
- Substituted benzofurans
- Substituted cathinones
- Substituted methylenedioxyphenethylamines
- Substituted phenethylamines
- Substituted tryptamines
References[edit]
- ^ 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
- ^ 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.
- ^ 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
Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction