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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2095200 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2843634	Partial Agonist 290

PubMed

Title	Date	PubMed
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.	1998 Jul	9655845
Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity.	2002 Aug 5	12113827
The effects of acute and subchronic treatment with fluoxetine and citalopram on stimulus control by DOM.	2002 Dec	12376156
Effect of 1-(3,4-methylenedioxyphenyl)-2-aminopropane and its optical isomers in PMMA-trained rats.	2002 May	11900801
Characterization of a novel effect of serotonin 5-HT1A and 5-HT2A receptors: increasing cGMP levels in rat frontal cortex.	2003 Dec	14614947
Characterization of the discriminative stimulus properties of centrally administered (-)-DOM and LSD.	2003 Feb	12543238
Discriminative stimulus properties of 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane [(+/-)DOI] in C57BL/6J mice.	2003 Feb	12474110
Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM.	2003 Jul	12957227
Low doses of non-NMDA glutamate receptor agonists alter neurobehavioural development in the rat.	2003 Jul-Aug	12798964
Functional study of rat 5-HT2A receptors using antisense oligonucleotides.	2003 Jun	12753068
Nefazodone in the rat: mimicry and antagonism of [-]-DOM-induced stimulus control.	2003 May	12873632
Cellular mechanisms of serotonin 5-HT2A receptor-mediated cGMP formation: the essential role of glutamate.	2004 Apr 2	15019576
Stimulus effects of three sulfur-containing psychoactive agents.	2004 Aug	15301941
Common drugs of abuse--Part II.	2004 Spring	15193009
Metabolic pathways of 4-bromo-2,5-dimethoxyphenethylamine (2C-B): analysis of phase I metabolism with hepatocytes of six species including human.	2005 Jan 5	15590110
Complex discriminative stimulus properties of (+)lysergic acid diethylamide (LSD) in C57Bl/6J mice.	2005 Jun	15645221
A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes.	2005 Mar 10	15639607
alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats.	2006 Oct	17112572
A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis.	2007 Aug	17526600
Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity.	2007 Jul	17551320
Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors.	2007 Jun	17337633
Metabolism and toxicological detection of the designer drug 4-iodo-2,5-dimethoxy-amphetamine (DOI) in rat urine using gas chromatography-mass spectrometry.	2007 Sep 15	17632045
Chronic phenethylamine hallucinogen treatment alters behavioral sensitivity to a metabotropic glutamate 2/3 receptor agonist.	2008 Aug	17957214
First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicological screening.	2008 Dec	19078842
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys.	2008 Feb	17993605
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.	2008 Nov	18604652
Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats.	2009 Jul	19288085
Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys: antagonism and apparent pA2 analyses.	2009 Mar	19098164
Modeling "psychosis" in vitro by inducing disordered neuronal network activity in cortical brain slices.	2009 Nov	19241062

Patents

Name

Type

Language

DOM

Common 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

2,5-DIMETHOXY-4-METHYLAMPHETAMINE

Systematic 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