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{{Short description|Class of chemical compounds}} |
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{{DISPLAYTITLE:DO |
{{DISPLAYTITLE:DO''x''}} |
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{{Other uses|Dox (disambiguation){{!}}Dox}} |
{{Other uses|Dox (disambiguation){{!}}Dox}} |
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[[File:2,5-DMA.png|thumb|200px|right|[[2,5-Dimethoxyamphetamine]] (2,5-DMA), the base structure of the DOx family]] |
[[File:2,5-DMA.png|thumb|200px|right|[[2,5-Dimethoxyamphetamine]] (2,5-DMA), the base structure of the DOx family]] |
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'''4-Substituted-2,5-dimethoxyamphetamines''' ('''DO''x''''') is a [[chemical class]] of [[Substitution reaction|substituted]] [[amphetamine]] [[derivative (chemistry)|derivatives]] featuring [[methoxy]] [[functional group|groups]] at the 2- and 5- positions of the [[phenyl]] [[simple aromatic ring|ring]], and a [[substituent]] such as [[alkyl]] or [[halogen]] at the 4- position of the phenyl ring.<ref name="Trachsel">{{cite book |author=Daniel Trachsel |author2=David Lehmann |author3=Christoph Enzensperger |name-list-style=amp |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}</ref> Most compounds of this class are [[potency (pharmacology)|potent]] and [[half-life|long-lasting]] [[psychedelic drug|psychedelic]] [[drug]]s, and act as highly [[functional selectivity|selective]] [[5-HT2A|5-HT<sub>2A</sub>]], [[5-HT2B|5-HT<sub>2B</sub>]], and [[5-HT2C|5-HT<sub>2C</sub>]] [[Receptor (biochemistry)|receptor]] [[partial agonist]]s. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT<sub>2</sub> receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects. |
'''4-Substituted-2,5-dimethoxyamphetamines''' ('''DO''x''''') is a [[chemical class]] of [[Substitution reaction|substituted]] [[amphetamine]] [[derivative (chemistry)|derivatives]] featuring [[methoxy]] [[functional group|groups]] at the 2- and 5- positions of the [[phenyl]] [[simple aromatic ring|ring]], and a [[substituent]] such as [[alkyl]] or [[halogen]] at the 4- position of the phenyl ring.<ref name="Trachsel">{{cite book |author=Daniel Trachsel |author2=David Lehmann |author3=Christoph Enzensperger |name-list-style=amp |year=2013 |title=Phenethylamine: Von der Struktur zur Funktion |publisher=Nachtschatten Verlag AG |isbn=978-3-03788-700-4}}</ref> Most compounds of this class are [[potency (pharmacology)|potent]] and [[half-life|long-lasting]] [[psychedelic drug|psychedelic]] [[drug]]s, and act as highly [[functional selectivity|selective]] [[5-HT2A|5-HT<sub>2A</sub>]], [[5-HT2B|5-HT<sub>2B</sub>]], and [[5-HT2C|5-HT<sub>2C</sub>]] [[Receptor (biochemistry)|receptor]] [[partial agonist]]s. A few bulkier derivatives such as DOAM have similarly high binding affinity for 5-HT<sub>2</sub> receptors but instead act as antagonists, and so do not produce psychedelic effects though they retain amphetamine-like stimulant effects. |
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==DOx derivatives== |
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The DO''x'' family includes the following members: |
The DO''x'' family includes the following members: |
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| 64638-07-9 (racemate) |
| 64638-07-9 (racemate) |
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| [[File:DOBU. |
| [[File:DOBU.svg|115px]] |
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| [[2,5-Dimethoxy-4-butylamphetamine]] |
| [[2,5-Dimethoxy-4-butylamphetamine]] |
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| DOBU |
| DOBU |
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| 123431-31-2 |
| 123431-31-2 |
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| [[File:MEM. |
| [[File:MEM.svg|115px]] |
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| [[2,5-Dimethoxy-4-ethoxyamphetamine]] |
| [[2,5-Dimethoxy-4-ethoxyamphetamine]] |
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| MEM |
| MEM |
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| DOEF |
| DOEF |
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| 121649-01-2 |
| 121649-01-2 |
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| [[File:DOPF_structure.png|115px]] |
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| 2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine |
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| [[DOPF]] |
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| [[File:DOI-racemic-skeletal.svg|115px]] |
| [[File:DOI-racemic-skeletal.svg|115px]] |
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| [[File:Aleph-6.svg|115px]] |
| [[File:Aleph-6.svg|115px]] |
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| [[Aleph (psychedelic)#Aleph-6 |
| [[Aleph (psychedelic)#Aleph-6|2,5-Dimethoxy-4-phenylthioamphetamine]] |
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| Aleph-6 |
| Aleph-6 |
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| 952006-44-9 |
| 952006-44-9 |
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| [[File:DO3MeOBZ structure.png|115px]] |
| [[File:DO3MeOBZ structure.png|115px]] |
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| 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine |
| 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine |
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| DO3MeOBZ <ref>Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007 |
| DO3MeOBZ <ref>[https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2007038372 Hellberg M, Namil A, Feng Z, Ward J. Phenylethylamine Analogs and Their Use for Treating Glaucoma. Patent WO 2007/038372, 6 Apr 2007]</ref> |
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| 930836-90-1 |
| 930836-90-1 |
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| [[File:DOTHFM_structure.png|115px]] |
| [[File:DOTHFM_structure.png|115px]] |
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| 2,5-Dimethoxy-4-[( |
| 2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine |
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| DOTHFM |
| DOTHFM |
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| 930776-12-8 |
| 930776-12-8 |
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| [[File:DOCN_structure.png|115px]] |
| [[File:DOCN_structure.png|115px]] |
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| 2,5-Dimethoxy-4-cyanoamphetamine |
| 2,5-Dimethoxy-4-cyanoamphetamine |
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| DOCN <ref>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}}</ref> |
| DOCN <ref>Seggel MR, Yousif MY, Lyon RA, Titeler M, [[Bryan Roth|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}}</ref> |
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| 125903-74-4 |
| 125903-74-4 |
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| [[File:DOYN_structure.png|115px]] |
| [[File:DOYN_structure.png|115px]] |
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| 2,5-Dimethoxy-4-ethynylamphetamine |
| 2,5-Dimethoxy-4-ethynylamphetamine |
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| DOYN <ref>{{cite journal | vauthors = Trachsel D | title = Synthesis of Novel (Phenylalkyl) amines for the Investigation of Structure–Activity Relationships, Part 3: |
| DOYN <ref>{{cite journal | vauthors = Trachsel D | title = 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). | journal = Helvetica Chimica Acta | date = August 2003 | volume = 86 | issue = 8 | pages = 2754–9 | doi = 10.1002/hlca.200390224 }}</ref> |
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| 633290-70-7 |
| 633290-70-7 |
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==Related compounds== |
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As well as the following members with additional substitutions: |
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A number of additional compounds are known with alternative substitutions: |
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{| class="wikitable" |
{| class="wikitable" |
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| 4C-D |
| 4C-D |
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| 52842-59-8 |
| 52842-59-8 |
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| [[File:4C-E_structure.png|115px]] |
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| 1-(2,5-Dimethoxy-4-ethylphenyl)butan-2-amine <ref>[https://patents.google.com/patent/US4034113A Shulgin AT. Treatment of senile geriatric patients to restore performance. Patent US 4034113]</ref> |
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| 4C-E |
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| [[File:4C-P_structure.png|115px]] |
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| 1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine |
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| 4C-P |
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| [[File:4C-B_structure.png|115px]] |
| [[File:4C-B_structure.png|115px]] |
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| 92206-37-6 |
| 92206-37-6 |
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| [[File:DMMDA. |
| [[File:DMMDA.svg|115px]] |
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| [[2,5-Dimethoxy-3,4-methylenedioxyamphetamine]] |
| [[2,5-Dimethoxy-3,4-methylenedioxyamphetamine]] |
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| DMMDA |
| DMMDA |
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| [[File:DOGO_structure.png|115px]] |
| [[File:DOGO_structure.png|115px]] |
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| 1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine |
| 1-(5,8-dimethoxy-3,4-dihydro-1H-isochromen-7-yl)propan-2-amine <ref>[https://patents.google.com/patent/US7396856 Hellberg MR, Namil A. Benzopyran analogs and their use for the treatment of glaucoma. Patent US 7396856]</ref> |
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| G-O |
| G-O |
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| 774538-38-4 |
| 774538-38-4 |
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| [[File:DODC_structure.png|115px]] |
| [[File:DODC_structure.png|115px]] |
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| 2,5-Dimethoxy-3,4-dichloroamphetamine |
| 2,5-Dimethoxy-3,4-dichloroamphetamine |
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| DODC |
| [[DODC]] |
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| 1373918-65-0 |
| 1373918-65-0 |
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| [[2,3,4,5-Tetramethoxyamphetamine]] |
| [[2,3,4,5-Tetramethoxyamphetamine]] |
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| 2,3,4,5-Tetramethoxyamphetamine |
| 2,3,4,5-Tetramethoxyamphetamine |
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| 23693-26-7 |
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| [[File:DOB-FLY_structure.png|115px]] |
| [[File:DOB-FLY_structure.png|115px]] |
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| DOB-DFLY |
| DOB-DFLY |
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| 502759-67-3 |
| 502759-67-3 |
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| [[File:WO2021-0137908-1_structure.png|115px]] |
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| 3-(4-bromo-2,5-dimethoxyphenyl)azetidine |
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| Compound 1,<ref>[https://patentimages.storage.googleapis.com/a2/12/19/8424e3822cbe82/US20210137908A1.pdf Kristensen J, et al. 5-HT2A Agonists for Use in Treatment of Depression. Patent US 2021/0137908]</ref> [[ZC-B]] |
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Latest revision as of 12:39, 24 June 2024
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 |
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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