Compounds > 2,5-dimethoxy-4-methylamphetamine
Page last updated: 2024-11-06

2,5-dimethoxy-4-methylamphetamine

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Description

2,5-Dimethoxy-4-Methylamphetamine: A psychedelic phenyl isopropylamine derivative, commonly called DOM, whose mood-altering effects and mechanism of action may be similar to those of LSD. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID85875
CHEMBL ID8600
SCHEMBL ID398119
MeSH IDM0006747

Synonyms (61)

Synonym
gtpl164
benzeneethanamine,2,5-dimethoxy-.alpha.,4-dimethyl-(.+/-.)-
1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
dl-4-methyl-2,5-dimethoxyamphetamine
2,5-dimethoxy-alpha,4-dimethylphenylethylamine
(rs)-dom
(+-)-1-(4-methyl-2,5-dimethoxyphenyl)-2-aminopropane
benzeneethanamine, 2,5-dimethoxy-alpha,4-dimethyl-
stp (hallucinogen)
dl-2,5-dimethoxy-4-methylamphetamine
(+-)-dom
2,5-dimethoxy-4,alpha-dimethylphenethylamin
dea no. 7395
4-methyl-2,5-dimethoxy-alpha-methylphenethylamine
2,5-dimethoxy-4-methylamphetamine
2,5-dimethoxymethylamphetamine
2,5-dimethoxy-4-methylphenylisopropylamine
(+-)-2,5-dimethoxy-4-methylamphetamine
2',5'-dimethoxy-4'-methylamphetamine
2-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
(+-)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
phenethylamine, 2,5-dimethoxy-alpha,4-dimethyl-
phenethylamine, 2,5-dimethoxy-.alpha.,4-dimethyl-
benzeneethanamine, 2,5-dimethoxy-.alpha.,4-dimethyl-
DOM ,
2,5 dimethoxy 4 methylamphetamine
DB01528
4-methyl-2,5-dimethoxyamphetamine
L000660
CHEMBL8600 ,
2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine
26011-50-7
dom,r(-)
(rec)2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine; compound with 2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine
2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine(dom)
(-)2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine
2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine((r)-(-)-dom)
(+/-)2-(2,5-dimethoxy-4-methyl-phenyl)-1-methyl-ethylamine
racemic dom
bdbm50005265
1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine
hsdb 7595
unii-uki9mld5oi
uki9mld5oi ,
15588-95-1
(+/-)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane
2,5-dimethoxy-.alpha.,4-dimethylphenylethylamine
4-methyl-2,5-dimethoxy-.alpha.-methylphenethylamine
j401.288g
dom [mi]
(+/-)-1-(4-methyl-2,5-dimethoxyphenyl)-2-aminopropane
(+/-)-2,5-dimethoxy-4-methylamphetamine
(+/-)-dom
2,5-dimethoxy-4-methylamphetamine [who-dd]
SCHEMBL398119
NTJQREUGJKIARY-UHFFFAOYSA-N
DTXSID50860611
benzeneethanamine,2,5-dimethoxy-a,4-dimethyl-
Q62267185
(rs)-2,5-dimethoxy-4-methylamphetamine
2,5-dimethoxy-4-methylamphamin

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" In the latter assay, both enantiomers of 6 had identical potencies, but their dose-response curves were not parallel."( Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA).
Frescas, SP; Johnson, MP; Nichols, DE; Oberlender, R, 1991)		0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki0.13100.00020.667710.0000AID4762; AID5263; AID5270
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.10000.00010.601710.0000AID385347; AID5263; AID5270
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki2.89000.00010.739610.0000AID3695
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki2.89000.00031.29679.2440AID3695
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Ki2.89000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Ki2.89000.00101.67479.2000AID3695
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki0.10000.00020.590910.0000AID5263; AID5270
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Kd0.07530.00042.58328.5114AID6405; AID6406
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Kd0.07530.00012.62198.5114AID6405; AID6406
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Kd0.07530.00012.29338.5114AID6405; AID6406
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1DRattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 1FRattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Kd0.07530.00042.47358.5114AID6405; AID6406
5-hydroxytryptamine receptor 6Rattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Kd0.07530.00012.70068.5114AID6405; AID6406
5-hydroxytryptamine receptor 5ARattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 5BRattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3ARattus norvegicus (Norway rat)Kd0.07530.00082.62148.5114AID6405; AID6406
5-hydroxytryptamine receptor 4 Rattus norvegicus (Norway rat)Kd0.07530.02342.74218.5114AID6405; AID6406
5-hydroxytryptamine receptor 3BRattus norvegicus (Norway rat)Kd0.07530.00082.62148.5114AID6405; AID6406
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (79)

Assay IDTitleYearJournalArticle
AID5551Compound was evaluated for its ability to displace [125I](R)-DOI from 5-hydroxytryptamine 2A receptor in cloned rat prefrontal cortex homogenate2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity.
AID5226Binding affinity against 5-hydroxytryptamine 2 receptor of rat frontal cortex using [3H]ketanserin radioligand1990Journal of medicinal chemistry, Mar, Volume: 33, Issue:3
A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors.
AID175588Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at 1 mg/kg + 5-OMe-iso-DMT (3 mg/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID177419Compound was evaluated for the drug discrimination assay and the ED50 (potency) was determined in rats1984Journal of medicinal chemistry, Jun, Volume: 27, Issue:6
Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane.
AID1130332Drug metabolism in rabbit liver microsomes assessed as 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane formation1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Chemical and biological studies of 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane, an analogue of 6-hydroxydopamine.
AID5243Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- 1-(4-bromo-2,5-dimethoxy-phenyl)-2-aminopropane (D) as radioligand in rat frontal cortex1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID167866Hyperthermic potency in rabbit relative to DOM1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID184726Number of animals responding /number of animals receiving at a dose of 1 mg/kg + 6-OMe-iso-DMT (1 mg/kg); 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID184730Number of animals responding /number of animals receiving 1 mg/kg + 5-OMe-iso-DMT (3 mg/kg); 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID192074Percent of animals selecting drug liver was determined at a dose of 2.03 intraperitoneally. (No. of animals disrupted:1)1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID1442386Induction of stimulus generalization in Sprague-Dawley rat trained to discriminate DOM assessed as appropriate responding level to training drug by two lever method2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID1442391Induction of stimulus generalization in rat trained to discriminate DOM assessed as appropriate responding level to training drug by two lever method2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID176211Effective dose was determined in the two-lever drug discrimination assay in rats trained to discriminate saline from injection of LSD tartarate administered intraperitoneally1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID23503Partition coefficient (logP)1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID175589Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at 1 mg/kg + 6-OMe-iso-DMT (1 mg/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID192716Compound was evaluated in stimulus generalization test using animals trained to discriminate TFMPP from saline, and the mean responses per min at dose of 1.0 mg/kg1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
5-HT1 and 5-HT2 binding characteristics of some quipazine analogues.
AID385349Lipophilicity of compound by immobilized artificial membrane column containing phosphatidylcholine head groups HPLC2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID5224Binding affinity against 5-hydroxytryptamine 2 receptor from rat frontal cortex using [125]-(R)-DOI as radioligand1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID1442390Induction of stimulus generalization in Sprague-Dawley rat trained to discriminate alpha-ET assessed as appropriate responding level to training drug by two lever method2017Journal of medicinal chemistry, 04-13, Volume: 60, Issue:7
The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.
AID191071Mean responses per minute during the extinction session 1 mg/kg + 6-OMe-iso-DMT (1 mg/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID175590Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at 1 mg/kg + saline (1 mL/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID4762Binding affinity towards 5-hydroxytryptamine 1C receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]mesulergine as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID176951Drug discrimination in LSD-trained rats2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity.
AID184717Number of animals responding /number of animals receiving 1 mg/kg + saline (1 mL/kg); 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID187810DOM appropriate response rate in % at 1.0 mg/kg where stimulus generalization occurred (5/5 no of animals)1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID5270Binding affinity to rat cortical membranes at 5-hydroxytryptamine 2 (5-HT2) receptor using [3H]KET as a radioligand1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID185149Compound was evaluated for the drug discrimination assay and the highest percent of LSD correct responses were determined in rats1984Journal of medicinal chemistry, Jun, Volume: 27, Issue:6
Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane.
AID241440Inhibitory concentration against monoamine oxidase A in rat brain mitochondrial suspension2005Journal of medicinal chemistry, Apr-07, Volume: 48, Issue:7
Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling.
AID5257Compound was evaluated for its ability to displace 0.25 nM [125I](R)-DOI from binding sites in rat frontal cortex.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID175587Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at 1 mg/kg + 5-OMe-iso-DMT (12 mg/kg); Disruption of behavior (i.e. no responding)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID5263Binding affinity towards 5-hydroxytryptamine 2 receptor from frontal cortical regions of male Sprague-Dawley rat homogenates, using [3H]ketanserin as radioligand1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID226641Hill coefficient of the compound1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID179049Compound was evaluated for the uptake inhibition of [3H]-5-HT in rats1991Journal of medicinal chemistry, May, Volume: 34, Issue:5
Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA).
AID177418Compound was evaluated for the drug discrimination assay and the ED50 (potency) was determined1986Journal of medicinal chemistry, Feb, Volume: 29, Issue:2
Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats.
AID189887Percentage of rats selecting the drug lever (% SDL) for dose 2.04(umol/kg)1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID1146450Competitive antagonist activity at 5-HT serotonin receptor in Sprague-Dawley rat stomach fundus model assessed as inhibition of 5-HT-induced contractile response1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues.
AID1131956Hallucinogenic activity in human1977Journal of medicinal chemistry, Dec, Volume: 20, Issue:12
Structure-activity studies on hallucinogenic amphetamines using molecular connectivity.
AID19263Log value of hallucinogenic activity was determined1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID191070Mean responses per minute during the extinction session 1 mg/kg + 5-OMe-iso-DMT (3 mg/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID4217Binding affinity against 5-hydroxytryptamine 1A receptor in rat hippocampal tissue1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID168357Stimulus generalization studies in TFMPP trained animals and the number of animals responding /number to receive dose of drug was determined at dose of 1.0 mg/kg; 10/101986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
5-HT1 and 5-HT2 binding characteristics of some quipazine analogues.
AID2330285-HT1C selectivity was defined as the ratio between Ki(5-HT2)/Ki(5-HT1C)1992Journal of medicinal chemistry, Feb-21, Volume: 35, Issue:4
Binding of phenylalkylamine derivatives at 5-HT1C and 5-HT2 serotonin receptors: evidence for a lack of selectivity.
AID176459Potency against LSD trained rat, activity is expressed as ED501995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID1130322Drug metabolism in rabbit liver homogenates assessed as assessed as 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane formation formation1979Journal of medicinal chemistry, Jun, Volume: 22, Issue:6
Chemical and biological studies of 1-(2,5-dihydroxy-4-methylphenyl)-2-aminopropane, an analogue of 6-hydroxydopamine.
AID176930Dose required to produce 50% hallucinogenic potency in rat was determined at a dose of 3.0 mg/kg1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID90250Human hallucinogenic activity relative to mescaline1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID385350Agonist activity at Sprague-Dawley rat 5HT2A receptor by drug discrimination assay2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID174440Compound was evaluated in stimulus generalization test using animals trained to discriminate TFMPP from saline, and the drug appropriate responding at dose of 1.0 mg/kg1986Journal of medicinal chemistry, Nov, Volume: 29, Issue:11
5-HT1 and 5-HT2 binding characteristics of some quipazine analogues.
AID184718Number of animals responding /number of animals receiving 1 mg/kg dose of drug; 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID184722Number of animals responding /number of animals receiving 6 mg/kg dose of drug; 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID191068Mean responses per minute during the extinction session at a dose of 1 mg/kg + saline (1 mL/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID175591Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at 1 mg/kg dose1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID6406Affinity against 5-hydroxytryptamine receptors in rat fundus model1980Journal of medicinal chemistry, Mar, Volume: 23, Issue:3
Serotonin receptor affinities of psychoactive phenalkylamine analogues.
AID1131839Inhibition of apomorphine-induced pecking in pigeon at 3 umol/kg1979Journal of medicinal chemistry, Aug, Volume: 22, Issue:8
N-Alkyl derivatives of (+/-)-alpha-methyldopamine.
AID184729Number of animals responding /number of animals receiving 1 mg/kg + 5-OMe-iso-DMT (12 mg/kg); 5/51984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID88883Hallucinogenic activity i.e; ratio of effective dose of mescaline to the effective dose in human1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID192068Percent of animals selecting drug liver was determined at a dose of 1.02 intraperitoneally. (No. of animals disrupted:0)1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID175598Responses made on the DOM -appropriate lever as a percent of total responses; data was collected during the 2.5 min extinction session at a dose of 1 mg/kg +saline (1 mL/kg.)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID189881Percentage of rats selecting the drug lever (% SDL) for dose 0.51(umol/kg)1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID19561Hill coefficient as determined.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID192066Percent of animals selecting drug liver was determined at a dose of 0.51 intraperitoneally. (No. of animals disrupted:0)1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.
AID3695Evaluated for binding affinity towards rat cortical membranes at 5-hydroxytryptamine 1 receptor binding site by using [3H]-5-HT as a radioligand.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Central serotonin receptors as targets for drug research.
AID189884Percentage of rats selecting the drug lever (% SDL) for dose 1.02(umol/kg)1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID190915DOM appropriate response of animals/min at 1.0 mg/kg where stimulus generalization occurred (5/5 no of animals)1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID4687Binding affinity against 5-HT1B serotonin receptor in rat striatum1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID6405Binding affinity at rat 5-hydroxytryptamine receptor.1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID5244Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- ketanserin as radioligand in rat frontal cortex1988Journal of medicinal chemistry, Apr, Volume: 31, Issue:4
N,N-di-n-propylserotonin: binding at serotonin binding sites and a comparison with 8-hydroxy-2-(di-n-propylamino)tetralin.
AID191069Mean responses per minute during the extinction session.1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID189882Percentage of rats selecting the drug lever (% SDL) for dose 0.77(umol/kg)1995Journal of medicinal chemistry, Sep-01, Volume: 38, Issue:18
Effect of a chiral 4-alkyl substituent in hallucinogenic amphetamines.
AID5732Compound was evaluated for its ability to displace [125I](R)-DOI from 5-hydroxytryptamine 2C receptor in cloned rat prefrontal cortex homogenate; ND denotes no data2002Bioorganic & medicinal chemistry letters, Aug-05, Volume: 12, Issue:15
Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity.
AID93042Hallucinogenic potency was determined in humans1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane.
AID191067Mean responses per minute during the extinction session 1 mg/kg + saline (1 mL/kg)1984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID385347Displacement of [3H]ketanserin from 5HT2A receptor in Sprague-Dawley rat brain by liquid scintillation spectroscopy2008Bioorganic & medicinal chemistry, Apr-15, Volume: 16, Issue:8
The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands.
AID5797Affinity against 5-hydroxytryptamine 2B receptor in the isolated rat stomach fundus1981Journal of medicinal chemistry, Dec, Volume: 24, Issue:12
Photoelectron spectra of psychotropic drugs. 6. Relationships between the physical properties and pharmacological actions of amphetamine analogues.
AID184731Number of animals responding /number of animals receiving 1 mg/kg + 6-OMe-iso-DMT (3 mg/kg); 6/61984Journal of medicinal chemistry, Jan, Volume: 27, Issue:1
Synthesis and evaluation of a novel series of N,N-dimethylisotryptamines.
AID178403Effective dose in rats trained on 1 mg/kg DOM.1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Structure-activity correlations for psychotomimetics. 1. Phenylalkylamines: electronic, volume, and hydrophobicity parameters.
AID91217Compound tested for hallucinogenic activity in humans was reported; Value reported in (A)= Mescaline units1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens.
AID624234Agonists at Rat 5-Hydroxytryptamine receptor 5-HT2A1998The Journal of pharmacology and experimental therapeutics, Jul, Volume: 286, Issue:1
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.
AID1346919Rat 5-HT2A receptor (5-Hydroxytryptamine receptors)1998The Journal of pharmacology and experimental therapeutics, Jul, Volume: 286, Issue:1
Creation of a constitutively activated state of the 5-hydroxytryptamine2A receptor by site-directed mutagenesis: inverse agonist activity of antipsychotic drugs.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (25)

TimeframeStudies, This Drug (%)All Drugs %
pre-199013 (52.00)18.7374
1990's8 (32.00)18.2507
2000's3 (12.00)29.6817
2010's1 (4.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 29.19

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index29.19 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index4.09 (4.65)
Search Engine Demand Index36.71 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other24 (96.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenethylamine
phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.		2.420alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
tryptamine
[no description available]		3.5120aminoalkylindole;
aralkylamino compound;
indole alkaloid;
tryptamines		human metabolite;
mouse metabolite;
plant metabolite
8-hydroxy-2-(di-n-propylamino)tetralin
8-Hydroxy-2-(di-n-propylamino)tetralin: A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin.. 8-OH-DPAT : A tetralin substituted at positions 1 and 7 by hydroxy and dipropylamino groups respectively		3.7830phenols;
tertiary amino compound;
tetralins		serotonergic antagonist
4-iodo-2,5-dimethoxyphenylisopropylamine
4-iodo-2,5-dimethoxyphenylisopropylamine: RN given refers to unlabeled parent cpd without isomeric designation; a serotonin agonist. 2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine : An organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4.		3.3870amphetamines;
dimethoxybenzene;
organoiodine compound
sk&f 10047
SKF-10,047 : An organic heterotricyclic compound that is metazocine in which the methyl group at the N-position is replaced by an allyl group.		2.1510
1-(1-naphthyl)piperazine
1-(1-naphthyl)piperazine: serotonin agonist; structure given in first source		3.4720N-arylpiperazine
1-(3-chlorophenyl)piperazine
1-(3-chlorophenyl)piperazine: supposed metabolite of TRAZODONE; RN given refers to parent cpd; structure. 1-(3-chlorophenyl)piperazine : A N-arylpiperazine that is piperazine carrying a 3-chlorophenyl substituent at position 1. It is a metabolite of the antidepressant drug trazodone.		3.0610monochlorobenzenes;
N-arylpiperazine		drug metabolite;
environmental contaminant;
serotonergic agonist;
xenobiotic
monomethylpropion
monomethylpropion: metabolite of dimethylpropion; structure given in first source. 2-methylamino-1-phenylpropan-1-one : An aromatic ketone that is propiophenone in which the hydrogen alpha- to the keto group has been replaced by a methylamino group.. methcathinone : A racemate comprising equal amounts of (R)- and (S)-methcathinone.		2.1510aromatic ketone;
secondary amino compound
3,4-methylenedioxyamphetamine
3,4-Methylenedioxyamphetamine: An amphetamine derivative that inhibits uptake of catecholamine neurotransmitters. It is a hallucinogen. It is less toxic than its methylated derivative but in sufficient doses may still destroy serotonergic neurons and has been used for that purpose experimentally.		3.4780benzodioxoles
n-methyl-3,4-methylenedioxyamphetamine
N-Methyl-3,4-methylenedioxyamphetamine: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.. 3,4-methylenedioxymethamphetamine : A member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5.		2.4220amphetamines;
benzodioxoles		neurotoxin
5-carboxamidotryptamine
5-carboxamidotryptamine: agonist of 5-HT receptor; structure given in first source		3.0610tryptamines
methylbufotenin
5-methoxy-N,N-dimethyltryptamine : A tryptamine alkaloid that is N,N-dimethyltryptamine substituted by a methoxy group at position 5.		3.7530aromatic ether;
tertiary amino compound;
tryptamine alkaloid		hallucinogen;
plant metabolite
5-methoxytryptamine
5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin.		3.4720aromatic ether;
primary amino compound;
tryptamines		5-hydroxytryptamine 2A receptor agonist;
5-hydroxytryptamine 2B receptor agonist;
5-hydroxytryptamine 2C receptor agonist;
antioxidant;
cardioprotective agent;
human metabolite;
mouse metabolite;
neuroprotective agent;
radiation protective agent;
serotonergic agonist
alpha-methylserotonin
alpha-methylserotonin: potent agonist at M & D receptors of serotonin; RN given refers to parent cpd		3.0610tryptaminesserotonergic agonist
buspirone
Buspirone: An anxiolytic agent and serotonin receptor agonist belonging to the azaspirodecanedione class of compounds. Its structure is unrelated to those of the BENZODIAZAPINES, but it has an efficacy comparable to DIAZEPAM.. buspirone : An azaspiro compound that is 8-azaspiro[4.5]decane-7,9-dione substituted at the nitrogen atom by a 4-(piperazin-1-yl)butyl group which in turn is substituted by a pyrimidin-2-yl group at the N(4) position.		3.5120azaspiro compound;
N-alkylpiperazine;
N-arylpiperazine;
organic heteropolycyclic compound;
piperidones;
pyrimidines		anxiolytic drug;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
sedative;
serotonergic agonist
chlorpromazine
Chlorpromazine: The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.. chlorpromazine : A substituted phenothiazine in which the ring nitrogen at position 10 is attached to C-3 of an N,N-dimethylpropanamine moiety.		1.9910organochlorine compound;
phenothiazines;
tertiary amine		anticoronaviral agent;
antiemetic;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
phenothiazine antipsychotic drug
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		4.3260primary amine
diazepam
Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.		2.15101,4-benzodiazepinone;
organochlorine compound		anticonvulsant;
anxiolytic drug;
environmental contaminant;
sedative;
xenobiotic
p-chloroamphetamine
p-Chloroamphetamine: Chlorinated analog of AMPHETAMINE. Potent neurotoxin that causes release and eventually depletion of serotonin in the CNS. It is used as a research tool.		2.0210
fenfluramine
Fenfluramine: A centrally active drug that apparently both blocks serotonin uptake and provokes transport-mediated serotonin release.. fenfluramine : A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reuptake pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding behavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertension.		2.1510(trifluoromethyl)benzenes;
secondary amino compound		appetite depressant;
serotonergic agonist;
serotonin uptake inhibitor
haloperidol
Haloperidol: A phenyl-piperidinyl-butyrophenone that is used primarily to treat SCHIZOPHRENIA and other PSYCHOSES. It is also used in schizoaffective disorder, DELUSIONAL DISORDERS, ballism, and TOURETTE SYNDROME (a drug of choice) and occasionally as adjunctive therapy in INTELLECTUAL DISABILITY and the chorea of HUNTINGTON DISEASE. It is a potent antiemetic and is used in the treatment of intractable HICCUPS. (From AMA Drug Evaluations Annual, 1994, p279). haloperidol : A compound composed of a central piperidine structure with hydroxy and p-chlorophenyl substituents at position 4 and an N-linked p-fluorobutyrophenone moiety.		1.9910aromatic ketone;
hydroxypiperidine;
monochlorobenzenes;
organofluorine compound;
tertiary alcohol		antidyskinesia agent;
antiemetic;
dopaminergic antagonist;
first generation antipsychotic;
serotonergic antagonist
p-hydroxyamphetamine
p-Hydroxyamphetamine: Amphetamine metabolite with sympathomimetic effects. It is sometimes called alpha-methyltyramine, which may also refer to the meta isomer, gepefrine.		2.1510amphetamines
ketanserin
Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.		4.0140aromatic ketone;
organofluorine compound;
piperidines;
quinazolines		alpha-adrenergic antagonist;
antihypertensive agent;
cardiovascular drug;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
serotonergic antagonist
mescaline
Mescaline: Hallucinogenic alkaloid isolated from the flowering heads (peyote) of Lophophora (formerly Anhalonium) williamsii, a Mexican cactus used in Indian religious rites and as an experimental psychotomimetic. Among its cellular effects are agonist actions at some types of serotonin receptors. It has no accepted therapeutic uses although it is legal for religious use by members of the Native American Church.. mescaline : A phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.		3.0750methoxybenzenes;
phenethylamine alkaloid;
primary amino compound		hallucinogen
mianserin
Mianserin: A tetracyclic compound with antidepressant effects. It may cause drowsiness and hematological problems. Its mechanism of therapeutic action is not well understood, although it apparently blocks alpha-adrenergic, histamine H1, and some types of serotonin receptors.. mianserin : A dibenzoazepine (specifically 1,2,3,4,10,14b-hexahydrodibenzo[c,f]pyrazino[1,2-a]azepine) methyl-substituted on N-2. Closely related to (and now mostly superseded by) the tetracyclic antidepressant mirtazapinean, it is an atypical antidepressant used in the treatment of depression throughout Europe and elsewhere.		3.4820dibenzoazepineadrenergic uptake inhibitor;
alpha-adrenergic antagonist;
antidepressant;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
geroprotector;
H1-receptor antagonist;
histamine agonist;
sedative;
serotonergic antagonist
1-(3-trifluoromethylphenyl)piperazine
1-(3-trifluoromethylphenyl)piperazine: acts as serotonin agonist; structure. 1-(3-(trifluoromethyl)phenyl)piperazine : A N-arylpiperazine that is piperazine substituted by a 3-(trifluoromethyl)phenyl group at position 1. A serotonergic agonist used as a recreational drug.		3.4720(trifluoromethyl)benzenes;
N-arylpiperazine		environmental contaminant;
psychotropic drug;
serotonergic agonist;
xenobiotic
octopamine
Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.		2.1510phenylethanolamines;
tyramines		neurotransmitter
o-methyltyramine
O-methyltyramine: RN given refers to parent cpd. 4-methoxyphenylethylamine : A primary amino compound consisting of ethylamine having a 4-methoxyphenyl substituent at the 2-position.		2.6530primary amino compound
pindolol
Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.		3.0610indoles;
secondary amine		antiglaucoma drug;
antihypertensive agent;
beta-adrenergic antagonist;
serotonergic antagonist;
vasodilator agent
pirenperone
[no description available]		3.0610aromatic ketone
psilocin
psilocin: psilocybine minus the phosphate ester; RN given refers to parent cpd; structure. psilocin : A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms").		2.3820hydroxyindoles;
phenols;
tertiary amino compound;
tryptamine alkaloid		drug metabolite;
fungal metabolite;
hallucinogen;
human xenobiotic metabolite;
serotonergic agonist
quipazine
Quipazine: A pharmacologic congener of serotonin that contracts smooth muscle and has actions similar to those of tricyclic antidepressants. It has been proposed as an oxytocic.		3.4720piperazines;
pyridines
risperidone
Risperidone: A selective blocker of DOPAMINE D2 RECEPTORS and SEROTONIN 5-HT2 RECEPTORS that acts as an atypical antipsychotic agent. It has been shown to improve both positive and negative symptoms in the treatment of SCHIZOPHRENIA.. risperidone : A member of the class of pyridopyrimidines that is 2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one carrying an additional 2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl group at position 2.		1.99101,2-benzoxazoles;
heteroarylpiperidine;
organofluorine compound;
pyridopyrimidine		alpha-adrenergic antagonist;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
H1-receptor antagonist;
psychotropic drug;
second generation antipsychotic;
serotonergic antagonist
ritanserin
Ritanserin: A selective and potent serotonin-2 antagonist that is effective in the treatment of a variety of syndromes related to anxiety and depression. The drug also improves the subjective quality of sleep and decreases portal pressure.. ritanserin : A thiazolopyrimidine that is 5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one which is substituted at position 7 by a methyl group and at position 6 by a 2-{4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl}ethyl group. A potent and long-acting seratonin (5-hydroxytryptamine, 5-HT) antagonist of the subtype 5-HT2 (Ki = 0.39 nM), it is used in the treatment of a variety of disorders including anxiety, depression and schizophrenia. It has little sedative action.		2.0410organofluorine compound;
piperidines;
thiazolopyrimidine		antidepressant;
antipsychotic agent;
anxiolytic drug;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
serotonergic antagonist
spiperone
Spiperone: A spiro butyrophenone analog similar to HALOPERIDOL and other related compounds. It has been recommended in the treatment of SCHIZOPHRENIA.. spiperone : An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.		3.4820aromatic ketone;
azaspiro compound;
organofluorine compound;
piperidines;
tertiary amino compound		alpha-adrenergic antagonist;
antipsychotic agent;
dopaminergic antagonist;
psychotropic drug;
serotonergic antagonist
tyramine
[no description available]		2.420monoamine molecular messenger;
primary amino compound;
tyramines		EC 3.1.1.8 (cholinesterase) inhibitor;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
neurotransmitter
lysergic acid diethylamide
Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.		2.8940ergoline alkaloid;
monocarboxylic acid amide;
organic heterotetracyclic compound		dopamine agonist;
hallucinogen;
serotonergic agonist
dextroamphetamine
Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.		2.89401-phenylpropan-2-amineadrenergic agent;
adrenergic uptake inhibitor;
dopamine uptake inhibitor;
dopaminergic agent;
neurotoxin;
sympathomimetic agent
n,n-dimethyltryptamine
N,N-Dimethyltryptamine: An N-methylated indoleamine derivative and serotonergic hallucinogen which occurs naturally and ubiquitously in several plant species including Psychotria veridis. It also occurs in trace amounts in mammalian brain, blood, and urine, and is known to act as an agonist or antagonist of certain SEROTONIN RECEPTORS.. N,N-dimethyltryptamine : A tryptamine derivative having two N-methyl substituents on the side-chain.		2.3820tryptamine alkaloid;
tryptamines
phenylpiperazine
phenylpiperazine: RN given refers to parent cpd		3.4720
etryptamine
etryptamine: RN given refers to cpd without isomeric designation		2.1510indoles
dimethoxyphenylethylamine
Dimethoxyphenylethylamine: A derivative of phenethylamine containing two substituent methoxy groups in the phenyl ring.. 3,4-dimethoxyphenylethylamine : An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.		2.6530alkaloid;
aromatic ether;
phenylethylamine		allergen;
plant metabolite
3,4-dimethoxyamphetamine
3,4-dimethoxyamphetamine: RN given refers to parent cpd without isomeric designation		4.3260
indopan
indopan: RN given refers to parent cpd without isomeric designation. alpha-methyltryptamine : A tryptamine derivative having a methyl substituent at the alpha-position.		2.1510tryptamines
ephedrine
Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.		2.1510phenethylamine alkaloid;
phenylethanolamines		bacterial metabolite;
environmental contaminant;
nasal decongestant;
plant metabolite;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic
apomorphine hydrochloride, anhydrous
[no description available]		1.9510
methysergide
Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches.		1.9910ergoline alkaloid
bufotenin
Bufotenin: A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.. bufotenin : A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5.		3.0610tertiary amine;
tryptamine alkaloid		coral metabolite;
hallucinogen
phenylpropanolamine
Phenylpropanolamine: A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.. phenylpropanolamine : An amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group. A decongestant and appetite suppressant, it is commonly used in prescription and over-the-counter cough and cold preparations.. (-)-norephedrine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid.		1.9510amphetamines;
phenethylamine alkaloid		plant metabolite
methamphetamine
Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.		2.1510amphetamines;
secondary amine		central nervous system stimulant;
environmental contaminant;
neurotoxin;
psychotropic drug;
xenobiotic
1,2-Dihydroquinolin-2-imine
[no description available]		1.9610aminoquinoline
3-phenylpropylamine
3-phenylpropylamine : A phenylalkylamine that is benzene in which one of the hydrogens is substituted by a 3-aminopropyl group.		1.9510benzenes;
phenylalkylamine;
primary amino compound
mmda
MMDA: RN given refers to parent cpd; structure		2.6630
2,5-dimethoxy-4-ethylamphetamine
2,5-dimethoxy-4-ethylamphetamine: psychedelic agent; ethyl homolog of dimethoxymethylamphetamine; RN given refers to parent cpd without isomeric designation		4.6890amphetamines
metergoline
Metergoline: A dopamine agonist and serotonin antagonist. It has been used similarly to BROMOCRIPTINE as a dopamine agonist and also for MIGRAINE DISORDERS therapy.. metergoline : An ergoline alkaloid that is the N-benzyloxycarbonyl derivative of lysergamine. A 5-HT2 antagonist. Also 5-HT1 antagonist and 5-HT1D ligand. Has moderate affinity for 5-HT6 and high affinity for 5-HT7.		3.0610carbamate ester;
ergoline alkaloid		dopamine agonist;
geroprotector;
serotonergic antagonist
2,4,5-trimethoxyphenylisopropylamine
2,4,5-trimethoxyphenylisopropylamine: RN given refers to parent cpd; structure		4.86110
4-methoxyamphetamine
4-methoxyamphetamine: para-methoxy derivative to amphetamine with hallucinogenic properties; minor descriptor (75-86); on line & INDEX MEDICUS search AMPHETAMINES (75-86); RN given refers to parent compound without isomeric designation		4.5780
l-amphetamine
(R)-amphetamine : A 1-phenylpropan-2-amine that has R configuration.		1.95101-phenylpropan-2-amine
2-aminotetralin
2-aminotetralin: RN given refers to parent cpd without isomeric designation; structure		1.9610tetralins
ipsapirone
[no description available]		3.0610N-arylpiperazine
2,5-dimethoxy-4-bromoamphetamine
2,5-dimethoxy-4-bromoamphetamine: RN given refers to (alpha)-isomer; a serotonin agonist that interferes with Meth A tumor growth in mice by selective vasoconstrictive action		5.09140
cathinone
cathinone: alkaloid from khat shrub, Catha edulis; RN given refers to parent cpd without isomeric designation. cathinone : The S stereoisomer of 2-aminopropiophenone.		2.4202-aminopropiophenone;
monoamine alkaloid		central nervous system stimulant;
psychotropic drug
2,5-dimethoxyamphetamine
2,5-dimethoxyamphetamine: RN given refers to parent cpd without isomeric designation		5.09140
mesulergine
mesulergine: RN given refers to parent cpd; CU 32-085 is synonymous to mono-HCl; metabolized into dopaminergic agonists; structure given in first source. mesulergine : A member of the class of ergot alkaloids that is known to act on serotonin and dopamine receptors.		3.0610ergot alkaloid;
sulfamides		antiparkinson drug;
dopamine agonist;
serotonergic antagonist
3,4-methylenedioxyphenethylamine
3,4-methylenedioxyphenethylamine: RN given refers to parent cpd		2.3720
3-methoxy-4-hydroxyphenylethylamine
3-methoxy-4-hydroxyphenylethylamine: a metabolite of dopamine and 5-hydroxytryptamine		1.9510
2-(2,5-dimethoxyphenyl)ethanamine
[no description available]		2.6730dimethoxybenzene
4-methoxymethamphetamine
4-methoxymethamphetamine: does not behave as a simple amphetamine-like agent; RN given refers to parent cpd without isomeric designation; structure given in first source		2.1510
2-(4-bromo-2,5-dimethoxyphenyl)ethylamine
2-(4-bromo-2,5-dimethoxyphenyl)ethylamine: behaves as a partial agonist toward both alpha1-adrenergic & 5-HT(2) serotonergic receptors. 2,5-dimethoxy-4-bromophenethylamine : A 2-arylethylamine compound where the aryl moiety is 4-bromo-2,5-dimethoxyphenyl.		2.39202-arylethylamine
n-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane
N-hydroxy-1-(3,4-methylenedioxyphenyl)-2-aminopropane: RN given refers to parent cpd		1.9910
3,4-methylenedioxyethamphetamine
3,4-methylenedioxyethamphetamine: legal replacement for MDMA; RN given for (+-)-isomer; structure given in first source. 1-(1,3-benzodioxol-5-yl)-N-ethylpropan-2-amine : A secondary amino compound that is N-ethylisopropylamine in which a hydrogen of one of the isopropyl methyl groups has been replaced by a 3,4-methylenedioxyphenyl group.		1.9910benzodioxoles;
secondary amino compound
1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane
1-(2,5-dimethoxy-4-nitrophenyl)-2-aminopropane: structure given in first source; RN given refers to parent cpd		4.1750
5-methoxy 3-(1,2,3,6-tetrahydro-4-pyridinyl)1h indole
[no description available]		3.0610indoles
n-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine
N-methyl-1-(1,3-benzodioxol-5-yl)-2-butanamine: structure given in first source; RN given refers to (+-)-isomer		1.9910
4-ethoxyamphetamine
4-ethoxyamphetamine: structure given in first source		2.420
1-(3,4-methylenedioxyphenyl)-2-butanamine
1-(3,4-methylenedioxyphenyl)-2-butanamine: RN given refers to cpd without isomeric designation; structure given in first source		1.9910benzodioxoles
n-methylserotonin
N-methylserotonin: RN given refers to parent cpd. N-methylserotonin : A member of the class of tryptamines that is serotonin in which one of the hydrogens attached to the primary amino group is replaced by a methyl group.		3.0610phenols;
tryptamines		human metabolite;
plant metabolite
4-methylthioamphetamine
4-methylthioamphetamine: structure given in first source		2.0210
3-methoxyamphetamine
3-methoxyamphetamine: RN given refers to cpd without isomeric designation		4.1750
n-desmethylmethoxyphenamine
N-desmethylmethoxyphenamine: metabolite of methoxyphenamine; RN given refers to parent cpd without isomeric designation		4.1750
6-hydroxytryptamine
6-hydroxytryptamine: RN given refers to parent cpd		3.0610
n,n-di-n-propylserotonin
N,N-di-n-propylserotonin: structure given in first source		1.9710
8-methoxy-2-(di-n-propylamino)tetralin
8-methoxy-2-(di-n-propylamino)tetralin: RN given refers to parent cpd without isomeric designation		2.4220
isomescaline
isomescaline: RN given refers to parent cpd		1.9710
norpseudoephedrine
norpseudoephedrine: major metabolite of diethylpropion in man under acidic urine conditions; RN given refers to cpd without isomeric designation;. cathine : An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer).		2.1510amphetamines;
phenethylamine alkaloid		central nervous system stimulant;
plant metabolite;
psychotropic drug
cocaine
Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.		2.1510benzoate ester;
methyl ester;
tertiary amino compound;
tropane alkaloid		adrenergic uptake inhibitor;
central nervous system stimulant;
dopamine uptake inhibitor;
environmental contaminant;
local anaesthetic;
mouse metabolite;
plant metabolite;
serotonin uptake inhibitor;
sodium channel blocker;
sympathomimetic agent;
vasoconstrictor agent;
xenobiotic
4-chloro-2,5-dimethoxyamphetamine
4-chloro-2,5-dimethoxyamphetamine: designer drug detected in rat urine		2.3920
2-(2,3-dihydroindol-1-yl)-N,N-dimethylethanamine
[no description available]		1.9610indoles
2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine
2-(2,5-dimethoxy-4-methylphenyl)cyclopropylamine: RN given refers to parent cpd without isomeric designation; structure		1.9910
sk&f 10047
[no description available]		2.1510
cinanserin
Cinanserin: A serotonin antagonist with limited antihistaminic, anticholinergic, and immunosuppressive activity.. cinanserin : An aryl sulfide that is (2E)-3-phenyl-N-(2-sulfanylphenyl)prop-2-enamide in which the hydrogen of the thiol group is substituted by a 3-(dimethylamino)propyl group. It is a 5-hydroxytryptamine receptor antagonist and an inhibitor of SARS-CoV replication.		3.0610aryl sulfide;
cinnamamides;
secondary carboxamide;
tertiary amino compound		anticoronaviral agent;
antiviral agent;
EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor
8-hydroxy-2-(di-n-propylamino)tetralin, (r)-isomer
[no description available]		2.1510tetralins
ms-245
N,N-dimethyl-2-(1-(benzenesulfonyl)-5-methoxy-1H-indol-3-yl)ethylamine: a 5-HT(6) receptor ligand; structure in first source		2.1510
4-iodo-2,5-dimethoxyphenylisopropylamine, (r)-isomer
[no description available]		3.7830
4-iodo-2,5-dimethoxy-beta-phenethylamine
4-iodo-2,5-dimethoxy-beta-phenethylamine: structure in first source		1.9910
2,5-dimethoxy-4-methylamphetamine, (r)-isomer
[no description available]		3.4820
2,5-dimethoxy-4-ethylthiophenethylamine
2,5-dimethoxy-4-ethylthiophenethylamine: structure in first source		1.9910
2,5-dimethoxy-4-bromoamphetamine, (r)-isomer
[no description available]		440
2,5-dimethoxy-4-bromoamphetamine, (s)-isomer
[no description available]		3.7630
2,5-dimethoxy-4-n-propylthiophenethylamine
2,5-dimethoxy-4-n-propylthiophenethylamine: structure in first source		1.9910
mme
[no description available]		1.9510
mephedrone
mephedrone: a beta-keto (bk) designer drug; Central Nervous System Stimulants. mephedrone : An aromatic ketone that is propiophenone substituted at C-4 and at C-beta with methyl and methylamino groups respectively. It is a synthetic stimulant and entactogen drug of the amphetamine and cathinone classes.		2.1510amphetamines;
aromatic ketone;
secondary amino compound		environmental contaminant;
xenobiotic
clozapine
Clozapine: A tricylic dibenzodiazepine, classified as an atypical antipsychotic agent. It binds several types of central nervous system receptors, and displays a unique pharmacological profile. Clozapine is a serotonin antagonist, with strong binding to 5-HT 2A/2C receptor subtype. It also displays strong affinity to several dopaminergic receptors, but shows only weak antagonism at the dopamine D2 receptor, a receptor commonly thought to modulate neuroleptic activity. Agranulocytosis is a major adverse effect associated with administration of this agent.. clozapine : A benzodiazepine that is 5H-dibenzo[b,e][1,4]diazepine substituted by a chloro group at position 8 and a 4-methylpiperazin-1-yl group at position 11. It is a second generation antipsychotic used in the treatment of psychiatric disorders like schizophrenia.		1.9910benzodiazepine;
N-arylpiperazine;
N-methylpiperazine;
organochlorine compound		adrenergic antagonist;
dopaminergic antagonist;
EC 3.4.21.26 (prolyl oligopeptidase) inhibitor;
environmental contaminant;
GABA antagonist;
histamine antagonist;
muscarinic antagonist;
second generation antipsychotic;
serotonergic antagonist;
xenobiotic
ConditionIndicatedRelationship StrengthStudiesTrials
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		02.3620