DOx: Difference between revisions

Content deleted Content added

Inline

Latest revision as of 12:39, 24 June 2024

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
^ 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

External links

[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] 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

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

@@ Line 1: / Line 1: @@
+{{Short description|Class of chemical compounds}}
-{{DISPLAYTITLE:DO<em>x</em>}}
+{{DISPLAYTITLE:DO''x''}}
 {{Other uses|Dox (disambiguation){{!}}Dox}}
 [[File:2,5-DMA.png|thumb|200px|right|[[2,5-Dimethoxyamphetamine]] (2,5-DMA), the base structure of the DOx family]]
 '''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.
+==DOx derivatives==
 The DO''x'' family includes the following members:
@@ Line 23: / Line 25: @@
 | 64638-07-9 (racemate)
 |-
-| [[File:DOBU.png|115px]]
+| [[File:DOBU.svg|115px]]
 | [[2,5-Dimethoxy-4-butylamphetamine]]
 | DOBU
@@ Line 33: / Line 35: @@
 | 123431-31-2
 |-
-| [[File:MEM.png|115px]]
+| [[File:MEM.svg|115px]]
 | [[2,5-Dimethoxy-4-ethoxyamphetamine]]
 | MEM
@@ Line 67: / Line 69: @@
 | DOEF
 | 121649-01-2
+|-
+| [[File:DOPF_structure.png|115px]]
+| 2,5-Dimethoxy-4-(3-fluoropropyl)amphetamine
+| [[DOPF]]
+|
 |-
 | [[File:DOI-racemic-skeletal.svg|115px]]
@@ Line 94: / Line 101: @@
 |-
 | [[File:Aleph-6.svg|115px]]
-| [[Aleph (psychedelic)#Aleph-6)|2,5-Dimethoxy-4-phenylthioamphetamine]]
+| [[Aleph (psychedelic)#Aleph-6|2,5-Dimethoxy-4-phenylthioamphetamine]]
 | Aleph-6
 | 952006-44-9
@@ Line 105: / Line 112: @@
 | [[File:DO3MeOBZ structure.png|115px]]
 | 2,5-Dimethoxy-4-(3-methoxybenzyl)amphetamine
-| 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.</ref>
+| 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>
 | 930836-90-1
 |-
 | [[File:DOTHFM_structure.png|115px]]
-| 2,5-Dimethoxy-4-[(tetrahydropyran-2-yl)methyl]amphetamine
+| 2,5-Dimethoxy-4-[(tetrahydrofuran-2-yl)methyl]amphetamine
 | DOTHFM
 | 930776-12-8
@@ Line 145: / Line 152: @@
 | [[File:DOCN_structure.png|115px]]
 | 2,5-Dimethoxy-4-cyanoamphetamine
-| 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>
 | 125903-74-4
 |-
 | [[File:DOYN_structure.png|115px]]
 | 2,5-Dimethoxy-4-ethynylamphetamine
-| 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>
+| 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>
 | 633290-70-7
 |-
 |}
+==Related compounds==
-As well as the following members with additional substitutions:
+A number of additional compounds are known with alternative substitutions:
 {| class="wikitable"
@@ Line 168: / Line 176: @@
 | 4C-D
 | 52842-59-8
+|-
+| [[File:4C-E_structure.png|115px]]
+| 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>
+| 4C-E
+|
+|-
+| [[File:4C-P_structure.png|115px]]
+| 1-(2,5-Dimethoxy-4-(n-propyl)phenyl)butan-2-amine
+| 4C-P
+|
 |-
 | [[File:4C-B_structure.png|115px]]
@@ Line 199: / Line 217: @@
 | 92206-37-6
 |-
-| [[File:DMMDA.png|115px]]
+| [[File:DMMDA.svg|115px]]
 | [[2,5-Dimethoxy-3,4-methylenedioxyamphetamine]]
 | DMMDA
@@ Line 225: / Line 243: @@
 |-
 | [[File:DOGO_structure.png|115px]]
-| 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>
 | G-O
 | 774538-38-4
@@ Line 231: / Line 249: @@
 | [[File:DODC_structure.png|115px]]
 | 2,5-Dimethoxy-3,4-dichloroamphetamine
-| DODC
+| [[DODC]]
 | 1373918-65-0
 |-
@@ Line 247: / Line 265: @@
 | [[2,3,4,5-Tetramethoxyamphetamine]]
 | 2,3,4,5-Tetramethoxyamphetamine
+| 23693-26-7
-|
 |-
 | [[File:DOB-FLY_structure.png|115px]]
@@ Line 258: / Line 276: @@
 | DOB-DFLY
 | 502759-67-3
+|-
+| [[File:WO2021-0137908-1_structure.png|115px]]
+| 3-(4-bromo-2,5-dimethoxyphenyl)azetidine
+| 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]]
+|
 |-
 |}

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 Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 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 ZDCM-04 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 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 Venlafaxine

Latest revision as of 12:39, 24 June 2024

DOx derivatives

Related compounds

See also

References

External links