Compounds > mesembrenone
Page last updated: 2024-12-08

mesembrenone

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

Description

mesembrenone: a psychoactive compound isolated from Sceletium tortuosum; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID216272
CHEMBL ID4781238
CHEBI ID6777
SCHEMBL ID226088
MeSH IDM000610470

Synonyms (26)

Synonym
mesembrenone
C09223 ,
AC1L50EL ,
(3ar,7as)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,7,7a-tetrahydroindol-6-one
6h-indol-6-one, 3a-(3,4-dimethoxyphenyl)-1,2,3,3a,7,7a-hexahydro-1-methyl-, (3ar-cis)-
ht8jns8e79 ,
(+)-mesembrenone
mesembrenone, (+)-
468-54-2
3a-(3,4-dimethoxyphenyl)-1,2,3,3a,7,7a-hexahydro-1-methyl-6h-indol-6-one (3ar-cis)-
unii-ht8jns8e79
SCHEMBL226088
CHEBI:6777
surecn226088
(3ar,7as)-3a-(3,4-dimethoxyphenyl)-1-methyl-1,2,3,3a,7,7a-hexahydro-6h-indol-6-one
bdbm50559715
chembl4781238 ,
Q6821189
DTXSID60963667
(3ar,7as)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,3a,6,7,7a-hexahydro-1h-indol-6-one
HY-124434
CS-0086461
(3ar,7as)-3a-(3,4-dimethoxyphenyl)-1,2,3,3a,7,7a-hexahydro-1-methyl-6h-indol-6-one
6h-indol-6-one, 3a-(3,4-dimethoxyphenyl)-1,2,3,3a,7,7a-hexahydro-1-methyl-, (3ar,7as)-
(+)-mesembrenine
AKOS040744433

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Despite the wide therapeutic applications of Sceletium extract, there are no reports of in vivo pharmacokinetic properties or analytical methods to quantify these two important alkaloids in plasma."( Quantification of mesembrine and mesembrenone in mouse plasma using UHPLC-QToF-MS: Application to a pharmacokinetic study.
Abe, N; Ashfaq, MK; Avula, B; Khan, IA; Khan, SI; Manda, VK, 2017)		0.74

Bioavailability

ExcerptReferenceRelevance
" However, the oral bioavailability of these alkaloids was poor and the plasma levels were below the detection limits."( Quantification of mesembrine and mesembrenone in mouse plasma using UHPLC-QToF-MS: Application to a pharmacokinetic study.
Abe, N; Ashfaq, MK; Avula, B; Khan, IA; Khan, SI; Manda, VK, 2017)		0.74
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrrolidinesAny of a class of heterocyclic amines having a saturated five-membered ring.
[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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium-dependent serotonin transporterHomo sapiens (human)Ki0.02700.00000.70488.1930AID1720043
cAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)IC50 (µMol)0.47000.00001.104010.0000AID1720042
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (46)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent serotonin transporterHomo sapiens (human)
response to hypoxiaSodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transportSodium-dependent serotonin transporterHomo sapiens (human)
response to nutrientSodium-dependent serotonin transporterHomo sapiens (human)
memorySodium-dependent serotonin transporterHomo sapiens (human)
circadian rhythmSodium-dependent serotonin transporterHomo sapiens (human)
response to xenobiotic stimulusSodium-dependent serotonin transporterHomo sapiens (human)
response to toxic substanceSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of gene expressionSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of serotonin secretionSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of cerebellar granule cell precursor proliferationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of synaptic transmission, dopaminergicSodium-dependent serotonin transporterHomo sapiens (human)
response to estradiolSodium-dependent serotonin transporterHomo sapiens (human)
social behaviorSodium-dependent serotonin transporterHomo sapiens (human)
vasoconstrictionSodium-dependent serotonin transporterHomo sapiens (human)
sperm ejaculationSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of neuron differentiationSodium-dependent serotonin transporterHomo sapiens (human)
positive regulation of cell cycleSodium-dependent serotonin transporterHomo sapiens (human)
negative regulation of organ growthSodium-dependent serotonin transporterHomo sapiens (human)
behavioral response to cocaineSodium-dependent serotonin transporterHomo sapiens (human)
enteric nervous system developmentSodium-dependent serotonin transporterHomo sapiens (human)
brain morphogenesisSodium-dependent serotonin transporterHomo sapiens (human)
serotonin uptakeSodium-dependent serotonin transporterHomo sapiens (human)
membrane depolarizationSodium-dependent serotonin transporterHomo sapiens (human)
platelet aggregationSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to retinoic acidSodium-dependent serotonin transporterHomo sapiens (human)
cellular response to cGMPSodium-dependent serotonin transporterHomo sapiens (human)
regulation of thalamus sizeSodium-dependent serotonin transporterHomo sapiens (human)
conditioned place preferenceSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion transmembrane transportSodium-dependent serotonin transporterHomo sapiens (human)
amino acid transportSodium-dependent serotonin transporterHomo sapiens (human)
neutrophil homeostasiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP catabolic processcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
neutrophil chemotaxiscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of type II interferon productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
positive regulation of interleukin-2 productioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
T cell receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
leukocyte migrationcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to lipopolysaccharidecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to xenobiotic stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cellular response to epinephrine stimuluscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of adenylate cyclase-activating adrenergic receptor signaling pathwaycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of cardiac muscle cell contractioncAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
negative regulation of relaxation of cardiac musclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
regulation of calcium ion transmembrane transport via high voltage-gated calcium channelcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP-mediated signalingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
integrin bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoatomic cation channel activitySodium-dependent serotonin transporterHomo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
serotonin:sodium:chloride symporter activitySodium-dependent serotonin transporterHomo sapiens (human)
protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent serotonin transporterHomo sapiens (human)
antiporter activitySodium-dependent serotonin transporterHomo sapiens (human)
syntaxin-1 bindingSodium-dependent serotonin transporterHomo sapiens (human)
cocaine bindingSodium-dependent serotonin transporterHomo sapiens (human)
sodium ion bindingSodium-dependent serotonin transporterHomo sapiens (human)
identical protein bindingSodium-dependent serotonin transporterHomo sapiens (human)
nitric-oxide synthase bindingSodium-dependent serotonin transporterHomo sapiens (human)
actin filament bindingSodium-dependent serotonin transporterHomo sapiens (human)
serotonin bindingSodium-dependent serotonin transporterHomo sapiens (human)
3',5'-cyclic-AMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
calcium channel regulator activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
protein bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cAMP bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
transmembrane transporter bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
metal ion bindingcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
3',5'-cyclic-GMP phosphodiesterase activitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Processvia Protein(s)Taxonomy
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
focal adhesionSodium-dependent serotonin transporterHomo sapiens (human)
endosome membraneSodium-dependent serotonin transporterHomo sapiens (human)
endomembrane systemSodium-dependent serotonin transporterHomo sapiens (human)
presynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
membrane raftSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
postsynaptic membraneSodium-dependent serotonin transporterHomo sapiens (human)
serotonergic synapseSodium-dependent serotonin transporterHomo sapiens (human)
synapseSodium-dependent serotonin transporterHomo sapiens (human)
plasma membraneSodium-dependent serotonin transporterHomo sapiens (human)
neuron projectionSodium-dependent serotonin transporterHomo sapiens (human)
centrosomecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
synaptic vesiclecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
postsynaptic densitycAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
Z disccAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
dendritic spinecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
excitatory synapsecAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
gamma-tubulin complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
voltage-gated calcium channel complexcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
nucleuscAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
perinuclear region of cytoplasmcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
cytosolcAMP-specific 3',5'-cyclic phosphodiesterase 4BHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID1720043Displacement of [3H]imipramine from recombinant human 5'-HT transporter expressed in CHO cells incubated for 60 mins by Scintillation counting method2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Advances in the Development of Phosphodiesterase-4 Inhibitors.
AID1720042Inhibition of recombinant human PDE4B expressed in baculovirus infected Sf9 cells using cAMP as substrate after 30 min by HTRF assay2020Journal of medicinal chemistry, 10-08, Volume: 63, Issue:19
Advances in the Development of Phosphodiesterase-4 Inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (57.14)24.3611
2020's3 (42.86)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.22

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 Index32.22 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index39.34 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
theophylline
[no description available]		3.3510dimethylxanthineadenosine receptor antagonist;
anti-asthmatic drug;
anti-inflammatory agent;
bronchodilator agent;
drug metabolite;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
fungal metabolite;
human blood serum metabolite;
immunomodulator;
muscle relaxant;
vasodilator agent
etazolate
Etazolate: A potent phosphodiesterase inhibitor proposed as an antipsychotic agent.. etazolate : A pyrazolopyridine that is 1H-pyrazolo[3,4-b]pyridine which is substituted at positions 1, 4, and 5 by ethyl, 2-isopropylidenehydrazino, and ethoxycarbonyl groups, respectively. A phosphodiesterase IV inhibitor with antidepressant and anxiolytic properties.		3.3510ethyl ester;
hydrazone;
pyrazolopyridine		alpha-secretase activator;
antidepressant;
antipsychotic agent;
anxiolytic drug;
GABA agent;
neuroprotective agent;
phosphodiesterase IV inhibitor
ibudilast
[no description available]		3.3510pyrazolopyridine
zardaverine
zardaverine: structure given in first source. zardaverine : A pyridazinone derivative in which pyridazin-3(2H)-one is substituted at C-6 with a 4-(difluoromethoxy)-3-methoxyphenyl group. It is a phosphodiesterase inhibitor, selective for PDE3 and 4.		3.3510organofluorine compound;
pyridazinone		anti-asthmatic drug;
bronchodilator agent;
EC 3.1.4.* (phosphoric diester hydrolase) inhibitor;
peripheral nervous system drug
cilomilast
[no description available]		3.3510methoxybenzenes
rp 73401
piclamilast: an antiasthmatic agent and phosphodiesterase 4 inhibitor; structure in first source. piclamilast : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 3-(cyclopentyloxy)-4-methoxybenzoic acid with the primary amino group of 3,5-dichloropyridin-4-amine.		3.3510aromatic ether;
benzamides;
chloropyridine;
monocarboxylic acid amide		anti-asthmatic drug;
anti-inflammatory agent;
bronchodilator agent;
phosphodiesterase IV inhibitor
roflumilast
[no description available]		3.3510aromatic ether;
benzamides;
chloropyridine;
cyclopropanes;
organofluorine compound		anti-asthmatic drug;
phosphodiesterase IV inhibitor
tetomilast
[no description available]		3.3510
naltrexone
Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.		2.1110cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic
gsk 256066
[no description available]		3.3510
rpl 554
ensifentrine: a phosphodiesterase 3/4 inhibitor; structure in first source		3.3510
apremilast
[no description available]		3.3510aromatic ether;
N-acetylarylamine;
phthalimides;
sulfone		non-steroidal anti-inflammatory drug;
phosphodiesterase IV inhibitor
an2728
crisaborole: NSAID, Dermatologic Agent; structure in first source. crisaborole : A member of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group. A phosphodiesterase 4 inhibitor that is used for treatment of mild to moderate atopic dermatitis in children and adults.		3.3510aromatic ether;
benzoxaborole;
nitrile		antipsoriatic;
non-steroidal anti-inflammatory drug;
phosphodiesterase IV inhibitor
chf6001
tanimilast: a phosphodiesterase-4 inhibitor; structure in first source		3.3510
mesembrine
[no description available]		3.0940
ConditionIndicatedRelationship StrengthStudiesTrials
Emesis
[description not available]		03.1710
Vomiting
The forcible expulsion of the contents of the STOMACH through the MOUTH.		03.1710
Anxiety
Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.		02.4110