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
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
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Intrahippocampal LSD accelerates learning and desensitizes the 5-HT(2A) receptor in the rabbit, Romano et al. | 2010-10 |
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| 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 |
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| LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor. | 2010-02 |
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| 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 |
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| Modeling "psychosis" in vitro by inducing disordered neuronal network activity in cortical brain slices. | 2009-11 |
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| Comparison of the discriminative stimulus effects of dimethyltryptamine with different classes of psychoactive compounds in rats. | 2009-07 |
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| Food restriction and streptozotocin differentially modify sensitivity to the hypothermic effects of direct- and indirect-acting serotonin receptor agonists in rats. | 2009-06-24 |
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| Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys: antagonism and apparent pA2 analyses. | 2009-03 |
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| 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 |
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| 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 |
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| 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 |
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| First case report of recreational use of 2,5-dimethoxy-4-chloroamphetamine confirmed by toxicological screening. | 2008-12 |
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| Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors. | 2008-11 |
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| Chronic phenethylamine hallucinogen treatment alters behavioral sensitivity to a metabotropic glutamate 2/3 receptor agonist. | 2008-08 |
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| [Bromo-dragon fly--life-threatening drug. Can cause tissue necrosis as demonstrated by the first described case]. | 2008-06-05 |
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| 'Hybrid' benzofuran-benzopyran congeners as rigid analogs of hallucinogenic phenethylamines. | 2008-06-01 |
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| 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 |
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| Metabolism and toxicological detection of the designer drug 4-chloro-2,5-dimethoxyamphetamine in rat urine using gas chromatography-mass spectrometry. | 2008-04 |
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| 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 |
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| Discriminative stimulus effects of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in rhesus monkeys. | 2008-02 |
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| 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 |
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| Distribution profile of 2,5-dimethoxy-4-bromoamphetamine (DOB) in rats after oral and subcutaneous doses. | 2007-08-06 |
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| A selective positive allosteric modulator of metabotropic glutamate receptor subtype 2 blocks a hallucinogenic drug model of psychosis. | 2007-08 |
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| Behavioral effects of dipropyltryptamine in rats: evidence for 5-HT1A and 5-HT2A agonist activity. | 2007-07 |
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| Dapoxetine, a novel selective serotonin transport inhibitor for the treatment of premature ejaculation. | 2007-06 |
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| Functional selectivity of hallucinogenic phenethylamine and phenylisopropylamine derivatives at human 5-hydroxytryptamine (5-HT)2A and 5-HT2C receptors. | 2007-06 |
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| Simultaneous determination of new thioamphetamine designer drugs in plasma by capillary electrophoresis coupled with mass spectrometry. | 2007 |
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| alpha-Ethyltryptamine (alpha-ET) as a discriminative stimulus in rats. | 2006-10 |
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| Study on metabolites of 2,5-dimethoxy-4-bromamphetamine (DOB) in human urine using gas chromatography-mass spectrometry. | 2005-12 |
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| Nonfatal and fatal DOB (2,5-dimethoxy-4-bromoamphetamine) overdose. | 2005-10-04 |
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| Hallucinogen-like actions of 2,5-dimethoxy-4-(n)-propylthiophenethylamine (2C-T-7) in mice and rats. | 2005-09 |
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| The stimulus properties of LSD in C57BL/6 mice. | 2005-08 |
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| Effects of clozapine and 2,5-dimethoxy-4-methylamphetamine [DOM] on 5-HT2A receptor expression in discrete brain areas. | 2005-08 |
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| Complex discriminative stimulus properties of (+)lysergic acid diethylamide (LSD) in C57Bl/6J mice. | 2005-06 |
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| A study of the metabolism of methamphetamine and 4-bromo-2,5-dimethoxyphenethylamine (2C-B) in isolated rat hepatocytes. | 2005-03-10 |
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| [Comparative study of the effects of amphetamine and dimethoxymethamphetamine on brain self-stimulation in rats after perinatal administration of 6-hydroxydopamine]. | 2005-02-15 |
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| 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 |
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| Beta-oxygenated analogues of the 5-HT2A serotonin receptor agonist 1-(4-bromo-2,5-dimethoxyphenyl)-2-aminopropane. | 2004-11-18 |
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| Lysergic acid diethylamide and [-]-2,5-dimethoxy-4-methylamphetamine increase extracellular glutamate in rat prefrontal cortex. | 2004-10-08 |
|
| A 5-HT(2C) receptor-mediated interaction between 2,5-dimethoxy-4-methylamphetamine and citalopram in the rat. | 2004-09 |
|
| Stimulus effects of three sulfur-containing psychoactive agents. | 2004-08 |
|
| Cellular mechanisms of serotonin 5-HT2A receptor-mediated cGMP formation: the essential role of glutamate. | 2004-04-02 |
|
| Common drugs of abuse--Part II. | 2004 |
|
| Characterization of a novel effect of serotonin 5-HT1A and 5-HT2A receptors: increasing cGMP levels in rat frontal cortex. | 2003-12 |
|
| Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM. | 2003-07 |
|
| Low doses of non-NMDA glutamate receptor agonists alter neurobehavioural development in the rat. | 2003-06-12 |
|
| Functional study of rat 5-HT2A receptors using antisense oligonucleotides. | 2003-06 |
|
| Nefazodone in the rat: mimicry and antagonism of [-]-DOM-induced stimulus control. | 2003-05 |
|
| Brain mechanisms of hallucinogens and entactogens. | 2001-12 |
|
| Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs. | 1998-07 |
Patents
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| Classification Tree | Code System | Code | ||
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WIKIPEDIA |
PiHKAL
Created by
admin on Mon Mar 31 21:27:11 GMT 2025 , Edited by admin on Mon Mar 31 21:27:11 GMT 2025
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WIKIPEDIA |
Designer-drugs-2,5-Dimethoxy-4-methylamphetamine
Created by
admin on Mon Mar 31 21:27:11 GMT 2025 , Edited by admin on Mon Mar 31 21:27:11 GMT 2025
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DEA NO. |
7395
Created by
admin on Mon Mar 31 21:27:11 GMT 2025 , Edited by admin on Mon Mar 31 21:27:11 GMT 2025
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| Code System | Code | Type | Description | ||
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7595
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DTXSID50860611
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100000144899
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26011-50-7
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11145
Created by
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2,5-DIMETHOXY-4-METHYLAMPHETAMINE
Created by
admin on Mon Mar 31 21:27:11 GMT 2025 , Edited by admin on Mon Mar 31 21:27:11 GMT 2025
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PRIMARY | 2,5-Dimethoxy-4-methylamphetamine (DOM; known on the street as STP, standing for "Serenity, Tranquility, and Peace") is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances.[1] It is generally taken orally. | ||
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85875
Created by
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UKI9MLD5OI
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SUB121767
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15588-95-1
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DB01528
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m4731
Created by
admin on Mon Mar 31 21:27:11 GMT 2025 , Edited by admin on Mon Mar 31 21:27:11 GMT 2025
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PRIMARY | Merck Index | ||
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18539-33-8
Created by
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SUPERSEDED |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
