DOM

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H19NO2
Molecular Weight	209.2848
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(C)=C(OC)C=C1CC(C)N

InChI

InChIKey=NTJQREUGJKIARY-UHFFFAOYSA-N

InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C12H19NO2
Molecular Weight	209.2848
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2 (5-HT2) receptor 90 Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2843634	Partial Agonist 297

PubMed

Title	Date	PubMed
Intrahippocampal LSD accelerates learning and desensitizes the 5-HT(2A) receptor in the rabbit, Romano et al.	2010-10	20827462
Differential effects of serotonin 5-HT1A receptor agonists on the discriminative stimulus effects of the 5-HT2A receptor agonist 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rats and rhesus monkeys.	2010-04	20053932
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor.	2010-02	19937319
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM), ketanserin, and (R)-(+)-{alpha}-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-pipidinemethanol (MDL100907) in rats.	2009-11	19687292
Modeling "psychosis" in vitro by inducing disordered neuronal network activity in cortical brain slices.	2009-11	19241062
Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats.	2009-07	19288085
Food restriction and streptozotocin differentially modify sensitivity to the hypothermic effects of direct- and indirect-acting serotonin receptor agonists in rats.	2009-06-24	19379724
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys: antagonism and apparent pA2 analyses.	2009-03	19098164
Effect of 8-hydroxy-2-(N,N-di-n-propylamino)tetralin and MDMA on the discriminative stimulus effects of the classical hallucinogen DOM in rats.	2009-01	18778728
Pharmacological properties and discriminative stimulus effects of a novel and selective 5-HT2 receptor agonist AL-38022A [(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine].	2009-01	18718483
2,5-Dimethoxyamphetamine-derived designer drugs: studies on the identification of cytochrome P450 (CYP) isoenzymes involved in formation of their main metabolites and on their capability to inhibit CYP2D6.	2008-12-15	18938231
First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicological screening.	2008-12	19078842
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.	2008-11	18604652
Chronic phenethylamine hallucinogen treatment alters behavioral sensitivity to a metabotropic glutamate 2/3 receptor agonist.	2008-08	17957214
[Bromo-dragon fly--life-threatening drug. Can cause tissue necrosis as demonstrated by the first described case].	2008-06-05	18522262
'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines.	2008-06-01	18467103
Disposition of 4-bromo-2,5-dimethoxyphenethylamine (2C-B) and its metabolite 4-bromo-2-hydroxy-5-methoxyphenethylamine in rats after subcutaneous administration.	2008-04-21	18339493
Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry.	2008-04	18259731
Designer drug 2,5-dimethoxy-4-methyl-amphetamine (DOM, STP): involvement of the cytochrome P450 isoenzymes in formation of its main metabolite and detection of the latter in rat urine as proof of a drug intake using gas chromatography-mass spectrometry.	2008-02-01	18155651
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys.	2008-02	17993605
Metabolism and toxicological detection of the designer drug 4-iodo-2,5-dimethoxy-amphetamine (DOI) in rat urine using gas chromatography-mass spectrometry.	2007-09-15	17632045
Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses.	2007-08-06	17629428
A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis.	2007-08	17526600
Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity.	2007-07	17551320
Dapoxetine, a novel selective serotonin transport inhibitor for the treatment of premature ejaculation.	2007-06	18360636
Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors.	2007-06	17337633
Simultaneous determination of new thioamphetamine designer drugs in plasma by capillary electrophoresis coupled with mass spectrometry.	2007	17955568
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.	2006-10	17112572
Study on metabolites of 2,5-dimethoxy-4-bromamphetamine (DOB) in human urine using gas chromatography-mass spectrometry.	2005-12	16601811
Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose.	2005-10-04	15979834
Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats.	2005-09	15983786
The stimulus properties of LSD in C57BL/6 mice.	2005-08	16005500
Effects of clozapine and 2,5-dimethoxy-4-methylamphetamine [DOM] on 5-HT2A receptor expression in discrete brain areas.	2005-08	15972234
Complex discriminative stimulus properties of (+)lysergic acid diethylamide (LSD) in C57Bl/6J mice.	2005-06	15645221
A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes.	2005-03-10	15639607
[Comparative study of the effects of amphetamine and dimethoxymethamphetamine on brain self-stimulation in rats after perinatal administration of 6-hydroxydopamine].	2005-02-15	15707006
Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human.	2005-01-05	15590110
Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane.	2004-11-18	15537358
Lysergic acid diethylamide and [-]-2,5-dimethoxy-4-methylamphetamine increase extracellular glutamate in rat prefrontal cortex.	2004-10-08	15364028
A 5-HT(2C) receptor-mediated interaction between 2,5-dimethoxy-4-methylamphetamine and citalopram in the rat.	2004-09	15388280
Stimulus effects of three sulfur-containing psychoactive agents.	2004-08	15301941
Cellular mechanisms of serotonin 5-HT2A receptor-mediated cGMP formation: the essential role of glutamate.	2004-04-02	15019576
Common drugs of abuse--Part II.	2004	15193009
Characterization of a novel effect of serotonin 5-HT1A and 5-HT2A receptors: increasing cGMP levels in rat frontal cortex.	2003-12	14614947
Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM.	2003-07	12957227
Low doses of non-NMDA glutamate receptor agonists alter neurobehavioural development in the rat.	2003-06-12	12798964
Functional study of rat 5-HT2A receptors using antisense oligonucleotides.	2003-06	12753068
Nefazodone in the rat: mimicry and antagonism of [-]-DOM-induced stimulus control.	2003-05	12873632
Brain mechanisms of hallucinogens and entactogens.	2001-12	22033605
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.	1998-07	9655845

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:27:11 GMT 2025` Edited by `admin` on `Mon Mar 31 21:27:11 GMT 2025`
Record UNII	UKI9MLD5OI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DOM

Common Name

English

2,5-DIMETHOXY-4-METHYLAMPHETAMINE

Preferred Name

English

DL-4-METHYL-2,5-DIMETHOXYAMPHETAMINE

Systematic Name

English

2,5-Dimethoxy-4-methylamphetamine [WHO-DD]

Common Name

English

2,5-DIMETHOXY-4-METHYLPHENYLISOPROPYLAMINE

Systematic Name

English

1-(2,5-DIMETHOXY-4-METHYLPHENYL)-2-AMINOPROPANE

Systematic Name

English

(±)-2,5-DIMETHOXY-4-METHYLAMPHETAMINE

Systematic Name

English

J401.288G

Code

English

(±)-1-(4-METHYL-2,5-DIMETHOXYPHENYL)-2-AMINOPROPANE

Systematic Name

English

DOM [MI]

Common Name

English

4-METHYL-2,5-DIMETHOXY-.ALPHA.-METHYLPHENETHYLAMINE

Systematic Name

English

(±)-DOM

Common Name

English

(RS)-DOM

Common Name

English

4-METHYL-2,5-DIMETHOXYAMPHETAMINE

Systematic Name

English

(±)-1-(2,5-DIMETHOXY-4-METHYLPHENYL)-2-AMINOPROPANE

Systematic Name

English

DL-2,5-DIMETHOXY-4-METHYLAMPHETAMINE

Systematic Name

English

2',5'-DIMETHOXY-4'-METHYLAMPHETAMINE

Common Name

English

2,5-DIMETHOXY-.ALPHA.,4-DIMETHYLPHENYLETHYLAMINE

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

PiHKAL