Page last updated: 2024-12-07

armepavine

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Description

Armepavine is a naturally occurring alkaloid found in various plants, particularly in the genus *Argemone*. It is a benzylisoquinoline alkaloid with a complex structure, characterized by a fused ring system. While its synthesis is not widely reported, it likely involves intricate reactions involving multiple steps. Armepavine exhibits diverse biological activities, including potential anti-inflammatory, analgesic, and antimicrobial effects. Its anti-inflammatory properties are attributed to its ability to inhibit the production of pro-inflammatory mediators. The analgesic effect of armepavine is thought to arise from its interaction with opioid receptors. Researchers are interested in understanding the mechanisms behind its biological activities and exploring its potential therapeutic applications, especially in areas like pain management and infectious diseases.'

armepavine: reticuline-like; RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID680292
CHEMBL ID1186477
MeSH IDM0178137
PubMed CID98348
CHEMBL ID451722
SCHEMBL ID1389166
MeSH IDM0178137

Synonyms (64)

Synonym
armepavine
4-[[(1s)-6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl]methyl]phenol
CHEMBL1186477
phenol, 4-(((1s)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-
14400-96-5
1alphah-armepavine
28w0aoi5pg ,
s-(+)-armepavine
unii-28w0aoi5pg
phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-, (s)-
(+)-armepavine
(s)-armepavine
armepavine, (+)-
l-(+)-armepavine
1.alpha.h-armepavine
Q27254354
(s)-4-((6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl)phenol
EX-A6387
DTXSID701317364
AKOS040749862
HMS1681O19
OPREA1_071832
UNM000011056201
(+/-) armepavine
4-[(6,7-dimethoxy-2-methyl-3,4-dihydro-1h-isoquinolin-1-yl)methyl]phenol
(+/-) phenol, 4-[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]-
OPREA1_262594
r-(-)-armepavine
phenol,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]-, (r)-
nsc110381
MLS000110731 ,
smr000106660
AKOS000591122
5884-67-3
(2,3,5,6-tetrabromobenzene-1,4-diyl)dimethanediyl diacetate
CHEMBL451722 ,
d,l-armepavine
inchi=1/c19h23no3/c1-20-9-8-14-11-18(22-2)19(23-3)12-16(14)17(20)10-13-4-6-15(21)7-5-13/h4-7,11-12,17,21h,8-10h2,1-3h3
zbkfziukxtwqtp-uhfffaoysa-
HMS2536C05
CCG-18658
8a0gw472w3 ,
phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-, (+-)-
armepavine, (+/-)-
unii-8a0gw472w3
(+-)-armepavine
p-cresol, .alpha.-(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolyl)-, (+/-)-
(+/-)-armepavine
dl-armepavine
phenol, 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-, (+/-)-
AB00290354-10
SCHEMBL1389166
AKOS025149602
OPERA_ID_467
4-[[(1s)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenol
SR-01000467236-1
sr-01000467236
bdbm50478474
STL560631
Q27270078
DTXSID50955773
3423-14-1
4-[(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]phenol
()-armepavine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
15-lipoxygenase, partialHomo sapiens (human)Potency25.11890.012610.691788.5700AID887
GLS proteinHomo sapiens (human)Potency19.95260.35487.935539.8107AID624170
Smad3Homo sapiens (human)Potency5.62340.00527.809829.0929AID588855
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency44.66840.011212.4002100.0000AID1030
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency50.11870.035520.977089.1251AID504332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID356081Displacement of [3H]prazosin from alpha1 adrenergic receptor in Wistar rat cerebral cortex membrane2003Journal of natural products, Jul, Volume: 66, Issue:7
Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action.
AID722233Inhibition of melanogenesis in mouse B16-4A5 cells at 1 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721319Inhibition of melanogenesis in mouse B16-4A5 cells after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721317Cytotoxicity against mouse B16-4A5 cells assessed as cell viability at 100 uM after 70 hrs by WST-8 assay2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721320Inhibition of melanogenesis in mouse B16-4A5 cells at 100 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721321Inhibition of melanogenesis in mouse B16-4A5 cells at 30 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID721318Cytotoxicity against mouse B16-4A5 cells assessed as cell viability at 30 uM after 70 hrs by WST-8 assay2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID356084Vasorelaxant activity against KCl-induced contraction in Wistar rat thoracic aorta in presence of calcium2003Journal of natural products, Jul, Volume: 66, Issue:7
Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action.
AID721322Inhibition of melanogenesis in mouse B16-4A5 cells at 10 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID356082Displacement of [3H]diltiazem from benzodiazepine binding site of L-type calcium channel in Wistar rat cerebral cortex membrane2003Journal of natural products, Jul, Volume: 66, Issue:7
Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action.
AID356083Vasorelaxant activity against noradrenaline-induced contraction in Wistar rat thoracic aorta in presence of calcium2003Journal of natural products, Jul, Volume: 66, Issue:7
Simplified tetrandrine congeners as possible antihypertensive agents with a dual mechanism of action.
AID722232Inhibition of melanogenesis in mouse B16-4A5 cells at 3 uM after 72 hrs by spectrophotometry2013Bioorganic & medicinal chemistry, Feb-01, Volume: 21, Issue:3
Alkaloid constituents from flower buds and leaves of sacred lotus (Nelumbo nucifera, Nymphaeaceae) with melanogenesis inhibitory activity in B16 melanoma cells.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588460High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, Validation Compound Set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588459High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588461High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, Validation compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1224864HCS microscopy assay (F508del-CFTR)2016PloS one, , Volume: 11, Issue:10
Increasing the Endoplasmic Reticulum Pool of the F508del Allele of the Cystic Fibrosis Transmembrane Conductance Regulator Leads to Greater Folding Correction by Small Molecule Therapeutics.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.76)18.7374
1990's0 (0.00)18.2507
2000's6 (28.57)29.6817
2010's12 (57.14)24.3611
2020's2 (9.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.56

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 Index22.56 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.56)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other12 (100.00%)84.16%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]