Page last updated: 2024-12-08

8-methoxy-2-(di-n-propylamino)tetralin

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Description

8-methoxy-2-(di-n-propylamino)tetralin: RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID193381
CHEMBL ID11760
SCHEMBL ID2218622
MeSH IDM0102615

Synonyms (15)

Synonym
8-methoxy-n,n-dipropyl-1,2,3,4-tetrahydronaphthalen-2-amine
8-ome-dpat
PDSP2_000015
PDSP1_000015
3897-94-7
CHEMBL11760 ,
bdbm50016737
(8-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-dipropyl-amine
(+)-8-methoxy-2-(di-n-propylamino)tetralin
2-naphthalenamine, 1,2,3,4-tetrahydro-8-methoxy-n,n-dipropyl-
8-methoxy-2-(di-n-propylamino)tetralin
SCHEMBL2218622
BCP34440
DTXSID00959822
PD075576

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The absolute oral bioavailability of compound 8 (8-triflate) was 4-5 times greater than the corresponding hydroxylated compound."( Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
Boije, M; Carlsson, A; Duncan, JN; Ekman, A; King, LJ; Martin, IJ; Romero, AG; Sonesson, C; Svensson, K; Wikström, H, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (21)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki1.66500.00020.667710.0000AID5108; AID5109
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki1.66500.00010.601710.0000AID5108; AID5109
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Ki0.00130.00020.561410.0000AID4035
5-hydroxytryptamine receptor 1ARattus norvegicus (Norway rat)Ki0.00170.00010.739610.0000AID1442380; AID4035; AID4411
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Ki0.00130.00020.635210.0000AID4035
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Ki0.00130.00020.621710.0000AID4035
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Ki0.00130.00020.675810.0000AID4035
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Ki0.00130.00020.646910.0000AID4035
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
5-hydroxytryptamine receptor 1BRattus norvegicus (Norway rat)Ki1.00000.00031.29679.2440AID4701
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Ki0.00130.00020.671210.0000AID4035
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki1.66500.00020.590910.0000AID5108; AID5109
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Ki0.00130.00020.557710.0000AID4035
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Ki0.00130.00020.640310.0000AID4035
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Ki0.00130.00020.570810.0000AID4035
GABA theta subunitRattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Ki0.00130.00020.656110.0000AID4035
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID4701Evaluated for binding affinity towards 5-hydroxytryptamine 1B receptor1988Journal 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.
AID1442380Displacement of [3H]-8-OH-DPAT from 5-HT1A receptor in rat hippocampal membranes2017Journal 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.
AID3595Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain hemispheral area by sc administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID3604Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain striatal area by po administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID61140Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain striatal area by po administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID3611Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain hemispheral area by po administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID177636Effect on 5-HTP accumulation in striatum of rat.1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.
AID61005Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain hemispheral area by sc administration; Inactive1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID4434Binding affinity against 5-hydroxytryptamine 1A receptor in homogenated rat brain tissue, using by [3H]8-OH-DPAT as radioligand1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID177496Effect on 5-HTP accumulation in hemispheres of rat.1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.
AID3599Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain limbic area by po administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID177647Effect on dopamine accumulation in striatum of rat; Inactive1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.
AID5108Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- 1-(4-bromo-2,5-dimethoxy-phenyl)-2-aminopropane (D) as radioligand1988Journal 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.
AID4035Binding affinity towards 5-hydroxytryptamine 1A receptor1988Journal 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.
AID3607Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain striatal area by sc administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID3601Effective dose for half-maximal decrease in the accumulation of 5-hydroxytryptophan (5-HTP) in reserpinized rat brain limbic area by sc administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID61143Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain striatal area by sc administration; Inactive1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID177645Effect on dopamine accumulation in limbic system of rat; Inactive1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.
AID61138Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain limbic area by sc administration; Inactive1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID5109Binding affinity towards 5-hydroxytryptamine 2 receptor using [3H]- ketanserin as radioligand1988Journal 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.
AID177634Effect on 5-HTP accumulation in limbic system of rat.1988Journal of medicinal chemistry, Jun, Volume: 31, Issue:6
Occurrence and pharmacological significance of metabolic ortho-hydroxylation of 5- and 8-hydroxy-2-(di-n-propylamino)tetralin.
AID61135Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain limbic area by po administration1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID3716Binding affinity at [3H]8-OH-DPAT-Labeled 5-hydroxytryptamine 1A receptor sites in rat brain hippocampal membranes expressed as Hill values1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
2-(Alkylamino)tetralin derivatives: interaction with 5-HT1A serotonin binding sites.
AID61004Effective dose for half-maximal decrease in the accumulation of DOPA in reserpinized rat brain hemispheral area by po administration; Inactive1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
AID4411Binding affinity of a compound to rat brain 5-hydroxytryptamine 1A (serotonin) receptor assayed by radiolabeled [3H]-8-OH-DPAT ligand displacement1996Journal of medicinal chemistry, Jan-05, Volume: 39, Issue:1
Binding of arylpiperazines, (aryloxy)propanolamines, and tetrahydropyridylindoles to the 5-HT1A receptor: contribution of the molecular lipophilicity potential to three-dimensional quantitative structure-affinity relationship models.
AID4051Binding affinity at [3H]8-OH-DPAT-Labeled 5-hydroxytryptamine 1A receptor sites in rat brain hippocampal membranes1989Journal of medicinal chemistry, Jan, Volume: 32, Issue:1
2-(Alkylamino)tetralin derivatives: interaction with 5-HT1A serotonin binding sites.
AID180898The dose at which the animals would show 50% responses on compound-appropriate lever1988Journal 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.
AID63962Binding affinity against dopamine receptor D2 in homogenated rat brain tissue, using by [3H]spiperone as radioligand1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Orally active central dopamine and serotonin receptor ligands: 5-, 6-, 7-, and 8-[[trifluoromethyl)sulfonyl]oxy]-2-(di-n-propylamino)tetralins and the formation of active metabolites in vivo.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (50.00)18.7374
1990's2 (25.00)18.2507
2000's1 (12.50)29.6817
2010's1 (12.50)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: 12.13

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.13 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]