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(Top) 1 DOx derivatives 2 Related compounds 3 See also 4 References 5 External links

DOx

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

4-Substituted-2,5-dimethoxyamphetamines (DOx) is a chemical classofsubstituted amphetamine derivatives featuring methoxy groups at the 2- and 5- positions of the phenyl ring, and a substituent such as alkylorhalogen 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[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

67707-78-2

Methyl-DOB

N-methyl-DOB

155638-80-5

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[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

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Antagonists: Adatanserin

Agomelatine

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Xylamidine

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Piperazines (e.g., naphthylpiperazine)

5-HT₆

Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide)

Hypidone

Serotonin (5-HT)

Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine)

WAY-181187

WAY-208466

Antagonists: ABT-354

Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone)

Latrepirdine (dimebolin)

Masupirdine

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, mianserin)

Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline)

Typical antipsychotics (e.g., chlorpromazine, loxapine)

Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide)

Piperazines (e.g., naphthylpiperazine)

5-HT₇

Agonists: 8-OH-DPAT

AS-19

Bifeprunox

E-55888

Ergolines (e.g., LSD)

Triptans (e.g., frovatriptan)

Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine)

Butaclamol

DR-4485

EGIS-12,233

Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)

JNJ-18038683

Ketanserin

LY-215,840

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)

Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine)

Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide)

Vortioxetine

Unknown/unsorted: Ergolines (e.g., lisuride, pergolide)

Piperazines (e.g., naphthylpiperazine)

See also: Receptor/signaling modulators

Adrenergics

Dopaminergics

Melatonergics

Monoamine reuptake inhibitors and releasing agents

Monoamine metabolism modulators

Monoamine neurotoxins

Human trace amine-associated receptor ligands

TAAR1

Agonists

Endogenous^†

Classical monoamine neurotransmitters
- Dopamine

Histamine

Epinephrine (adrenaline)

Norepinephrine (noradrenaline)

Serotonin

Trace amines

Synthetic and natural^‡

Amphetamine

DOB

DOET

N,N-Dimethylphenethylamine

MDMA (midomafetamine)

2-Methylphenethylamine

3-Methylphenethylamine

4-Methylphenethylamine

β-Methylphenethylamine

Ralmitaront (RG-7906, RO-6889450)

RO5166017

Selegiline

Solriamfetol

Ulotaront (SEP-363856)

Neutral antagonists

Inverse agonists

EPPTB (RO5212773)

TAAR2

Agonists^‡

Neutral antagonists

TAAR5

Agonists^‡

N,N-Dimethylethylamine

Trimethylamine

Neutral antagonists

Inverse agonists^‡

3-Iodothyronamine

^† References for all endogenous human TAAR1 ligands are provided at List of trace amines

^‡ References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.

See also: Receptor/signaling modulators