Page last updated: 2024-12-08

nantenine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

nantenine: from Nandina domestica Thundberg; RN given refers to (S)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Nandinagenus[no description available]BerberidaceaeThe Barberry plant family of the order Ranunculales, subclass Magnoliidae, class Magnoliopsida. The shrubs have spiny leaves.[MeSH]
Nandina domesticaspecies[no description available]BerberidaceaeThe Barberry plant family of the order Ranunculales, subclass Magnoliidae, class Magnoliopsida. The shrubs have spiny leaves.[MeSH]

Cross-References

ID SourceID
PubMed CID197001
CHEMBL ID179440
CHEBI ID68992
SCHEMBL ID1254592
MeSH IDM0123344

Synonyms (36)

Synonym
nantenine
ccris 3807
domesticine, o-methyl-
o-methyldomesticine
6a-alpha-aporphine, 1,2-dimethoxy-9,10-(methylenedioxy)-
nantenin
domestine
(s)-1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-9,11-dioxa-6-aza-benzo[fg]cyclopenta[b]anthracene
bdbm50160160
CHEMBL179440 ,
chebi:68992 ,
C19985
unii-xe0au8c122
xe0au8c122 ,
2565-01-7
nanteine
(+)-domestine
domesticine methyl ether
4h-benzo(de)(1,3)benzodioxolo(5,6-g)quinoline, 5,6,6a,7-tetrahydro-1,2-methoxy-6-methyl-, (6as)-
(+)-nantenine
domesticine methyl ether [mi]
SCHEMBL1254592
1,2-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-benzo[de][1,3]benzodioxolo[5,6-g]quinoline-, (s)-
WSVWKHTVFGTTKJ-AWEZNQCLSA-N
6a.alpha.-aporphine, 1,2-dimethoxy-9,10-(methylenedioxy)-
4h-benzo[de][1,3]benzodioxolo[5,6-g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (s)-
DTXSID70180343
(+)-domestine (nantenine)
Q13566119
(12s)-18,19-dimethoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaene
nsc-785161
nsc785161
4h-benzo[de][1,3]benzodioxolo[5,6-g]quinoline, 5,6,6a,7-tetrahydro-1,2-dimethoxy-6-methyl-, (6as)-
AKOS040762093
HY-N9141
CS-0158840

Research Excerpts

Overview

Nantenine functions as an effective antagonist against a wide range of MDMA-induced effects in mice.

ExcerptReferenceRelevance
"Nantenine functions as an effective antagonist against a wide range of MDMA-induced effects in mice. "( Nantenine: an antagonist of the behavioral and physiological effects of MDMA in mice.
Chen, X; Fantegrossi, WE; Karabenick, RL; Kiessel, CL; Leach, PT; Ohizumi, Y; Rice, KC; Ullrich, T; Van Martin, C; Woods, JH, 2004
)
3.21
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
oxoaporphine alkaloidAny aporphine alkaloid that has a 7-keto-4H-dibenzo[de,g]quinoline skeleton. The oxoaporphine alkaloids are found in members of the Anonacea, Aracea, Hernandiaceae, Lauraceae, Magnoliaceae, Menispermaceae, Monimiaceae, Papaveraceae, and Ranunculaceae families.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ke0.65700.03200.59730.8500AID1130112
Alpha-1A adrenergic receptorHomo sapiens (human)Ke0.19600.00110.05850.1960AID1130113
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (68)

Processvia Protein(s)Taxonomy
temperature homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytokine production involved in immune response5-hydroxytryptamine receptor 2AHomo sapiens (human)
glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
intracellular calcium ion homeostasis5-hydroxytryptamine receptor 2AHomo sapiens (human)
activation of phospholipase C activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cytosolic calcium ion concentration5-hydroxytryptamine receptor 2AHomo sapiens (human)
memory5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 2AHomo sapiens (human)
response to xenobiotic stimulus5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of phosphatidylinositol biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
regulation of dopamine secretion5-hydroxytryptamine receptor 2AHomo sapiens (human)
artery smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
urinary bladder smooth muscle contraction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of heat generation5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of potassium ion transport5-hydroxytryptamine receptor 2AHomo sapiens (human)
phosphatidylinositol 3-kinase/protein kinase B signal transduction5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of neuron apoptotic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein localization to cytoskeleton5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of fat cell differentiation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of glycolytic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of vasoconstriction5-hydroxytryptamine receptor 2AHomo sapiens (human)
symbiont entry into host cell5-hydroxytryptamine receptor 2AHomo sapiens (human)
sensitization5-hydroxytryptamine receptor 2AHomo sapiens (human)
behavioral response to cocaine5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of inflammatory response5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of peptidyl-tyrosine phosphorylation5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of temperature stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
detection of mechanical stimulus involved in sensory perception of pain5-hydroxytryptamine receptor 2AHomo sapiens (human)
release of sequestered calcium ion into cytosol5-hydroxytryptamine receptor 2AHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergic5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascade5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic modulation of chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of execution phase of apoptosis5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of platelet aggregation5-hydroxytryptamine receptor 2AHomo sapiens (human)
positive regulation of DNA biosynthetic process5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 2AHomo sapiens (human)
phospholipase C-activating serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 2AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 2AHomo sapiens (human)
MAPK cascadeAlpha-1A adrenergic receptorHomo sapiens (human)
negative regulation of heart rate involved in baroreceptor response to increased systemic arterial blood pressureAlpha-1A adrenergic receptorHomo sapiens (human)
norepinephrine-epinephrine vasoconstriction involved in regulation of systemic arterial blood pressureAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of heart rate by epinephrine-norepinephrineAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of the force of heart contraction by epinephrine-norepinephrineAlpha-1A adrenergic receptorHomo sapiens (human)
apoptotic processAlpha-1A adrenergic receptorHomo sapiens (human)
smooth muscle contractionAlpha-1A adrenergic receptorHomo sapiens (human)
signal transductionAlpha-1A adrenergic receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayAlpha-1A adrenergic receptorHomo sapiens (human)
activation of phospholipase C activityAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationAlpha-1A adrenergic receptorHomo sapiens (human)
adult heart developmentAlpha-1A adrenergic receptorHomo sapiens (human)
negative regulation of cell population proliferationAlpha-1A adrenergic receptorHomo sapiens (human)
response to xenobiotic stimulusAlpha-1A adrenergic receptorHomo sapiens (human)
response to hormoneAlpha-1A adrenergic receptorHomo sapiens (human)
negative regulation of autophagyAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of cardiac muscle hypertrophyAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAlpha-1A adrenergic receptorHomo sapiens (human)
intracellular signal transductionAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of MAPK cascadeAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of action potentialAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of vasoconstrictionAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of smooth muscle contractionAlpha-1A adrenergic receptorHomo sapiens (human)
calcium ion transport into cytosolAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of cardiac muscle contractionAlpha-1A adrenergic receptorHomo sapiens (human)
cell growth involved in cardiac muscle cell developmentAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeAlpha-1A adrenergic receptorHomo sapiens (human)
positive regulation of protein kinase C signalingAlpha-1A adrenergic receptorHomo sapiens (human)
pilomotor reflexAlpha-1A adrenergic receptorHomo sapiens (human)
neuron-glial cell signalingAlpha-1A adrenergic receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayAlpha-1A adrenergic receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayAlpha-1A adrenergic receptorHomo sapiens (human)
cell-cell signalingAlpha-1A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
Gq/11-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
virus receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein tyrosine kinase activator activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
identical protein binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
protein-containing complex binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding5-hydroxytryptamine receptor 2AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 2AHomo sapiens (human)
alpha1-adrenergic receptor activityAlpha-1A adrenergic receptorHomo sapiens (human)
protein bindingAlpha-1A adrenergic receptorHomo sapiens (human)
protein heterodimerization activityAlpha-1A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
neurofilament5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
caveola5-hydroxytryptamine receptor 2AHomo sapiens (human)
axon5-hydroxytryptamine receptor 2AHomo sapiens (human)
cytoplasmic vesicle5-hydroxytryptamine receptor 2AHomo sapiens (human)
presynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
neuronal cell body5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendritic shaft5-hydroxytryptamine receptor 2AHomo sapiens (human)
postsynaptic membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
cell body fiber5-hydroxytryptamine receptor 2AHomo sapiens (human)
glutamatergic synapse5-hydroxytryptamine receptor 2AHomo sapiens (human)
G protein-coupled serotonin receptor complex5-hydroxytryptamine receptor 2AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 2AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 2AHomo sapiens (human)
nucleusAlpha-1A adrenergic receptorHomo sapiens (human)
nucleoplasmAlpha-1A adrenergic receptorHomo sapiens (human)
cytoplasmAlpha-1A adrenergic receptorHomo sapiens (human)
cytosolAlpha-1A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-1A adrenergic receptorHomo sapiens (human)
caveolaAlpha-1A adrenergic receptorHomo sapiens (human)
nuclear membraneAlpha-1A adrenergic receptorHomo sapiens (human)
intracellular membrane-bounded organelleAlpha-1A adrenergic receptorHomo sapiens (human)
plasma membraneAlpha-1A adrenergic receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID1130113Antagonist activity at alpha1A adrenergic receptor (unknown origin) assessed as inhibition of mobilization of internal calcium at 10 uM by FLIPR assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Evaluation of structural effects on 5-HT(2A) receptor antagonism by aporphines: identification of a new aporphine with 5-HT(2A) antagonist activity.
AID1130114Selectivity ratio of Ke for human 5-HT2A receptor to Ke for alpha1A adrenergic receptor (unknown origin)2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Evaluation of structural effects on 5-HT(2A) receptor antagonism by aporphines: identification of a new aporphine with 5-HT(2A) antagonist activity.
AID1130111Intrinsic agonist activity at human 5-HT2A receptor assessed as mobilization of internal calcium at 10 uM by FLIPR assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Evaluation of structural effects on 5-HT(2A) receptor antagonism by aporphines: identification of a new aporphine with 5-HT(2A) antagonist activity.
AID239068Binding constant measured against Alpha-1A adrenergic receptor in human prostate; +:inactive2005Bioorganic & medicinal chemistry letters, Feb-01, Volume: 15, Issue:3
Pharmacophore identification of alpha(1A)-adrenoceptor antagonists.
AID1130112Antagonist activity at human 5-HT2A receptor assessed as inhibition of 5-HT-induced mobilization of internal calcium at 10 uM by FLIPR assay2014Bioorganic & medicinal chemistry letters, Apr-01, Volume: 24, Issue:7
Evaluation of structural effects on 5-HT(2A) receptor antagonism by aporphines: identification of a new aporphine with 5-HT(2A) antagonist activity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (3.70)18.7374
1990's0 (0.00)18.2507
2000's15 (55.56)29.6817
2010's11 (40.74)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: 24.05

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 Index24.05 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.74 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.05)

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%
Other27 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]