hirsutine, (16e,20beta)-isomer profile

ID Source	ID
PubMed CID	3000341
CHEMBL ID	60533
CHEBI ID	70073
SCHEMBL ID	4146368
MeSH ID	M0320962

Synonym
nsc 72135
indolo[2,3-a]quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-.alpha.-(methoxymethylene)-, methyl ester, (.alpha.e,2s,3s,12bs)-
23407-35-4
corynantheidine
NSC72135 ,
methyl (e)-2-[(2s,3s,12bs)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxy-prop-2-enoate
CHEMBL60533
corynanrheidine
chebi:70073 ,
methyl (e)-2-[(2s,3s,12bs)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
unii-qmp2rf3l41
qmp2rf3l41 ,
indolo(2,3-a)quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)-, methyl ester, (alphae,2s,3s,12bs)-
SCHEMBL4146368
(-)-corynantheidine
epidihydrocorynantheine
indolo(2,3-a)quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-.alpha.-(methoxymethylene)-, methyl ester, (2s-(2.alpha.(e),3.alpha.,12b.beta.))-
indolo(2,3-a)quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-.alpha.-(methoxymethylene)-, methyl ester, (.alpha.e,2s,3s,12bs)-
17,18-seco-20.alpha.-yohimban-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (e)- corynan-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (16e,20.beta.)-
bdbm50474149
Q27138411
methyl (alphae,2s,3s,12bs)-3-ethyl-1,2,3,4,6,7,12,12b-octahydro-alpha-(methoxymethylene)indolo[2,3-a]quinolizine-2-acetate
DTXSID801106946

Role	Description
metabolite	Any 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]

Class	Description
alkaloid	Any of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Cytochrome P450 2D6	Homo sapiens (human)	Ki	2.8000	0.0001	1.1986	8.0000	AID1775306
Alpha-1D adrenergic receptor	Homo sapiens (human)	Ki	0.0417	0.0000	0.3609	10.0000	AID1581730
Mu-type opioid receptor	Homo sapiens (human)	Ki	1.0140	0.0000	0.4197	10.0000	AID1581727; AID1749821
Kappa-type opioid receptor	Homo sapiens (human)	Ki	1.9100	0.0000	0.3624	10.0000	AID1581726
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
xenobiotic metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
steroid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
cholesterol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
estrogen metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
coumarin metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
alkaloid catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
monoterpenoid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
isoquinoline alkaloid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
xenobiotic catabolic process	Cytochrome P450 2D6	Homo sapiens (human)
retinol metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
long-chain fatty acid biosynthetic process	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidative demethylation	Cytochrome P450 2D6	Homo sapiens (human)
negative regulation of cellular organofluorine metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
arachidonic acid metabolic process	Cytochrome P450 2D6	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Alpha-1D adrenergic receptor	Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathway	Alpha-1D adrenergic receptor	Homo sapiens (human)
positive regulation of cell population proliferation	Alpha-1D adrenergic receptor	Homo sapiens (human)
neuron-glial cell signaling	Alpha-1D adrenergic receptor	Homo sapiens (human)
cell-cell signaling	Alpha-1D adrenergic receptor	Homo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathway	Alpha-1D adrenergic receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Alpha-1D adrenergic receptor	Homo sapiens (human)
positive regulation of cytosolic calcium ion concentration	Alpha-1D adrenergic receptor	Homo sapiens (human)
positive regulation of vasoconstriction	Alpha-1D adrenergic receptor	Homo sapiens (human)
positive regulation of MAPK cascade	Alpha-1D adrenergic receptor	Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	Mu-type opioid receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
sensory perception	Mu-type opioid receptor	Homo sapiens (human)
negative regulation of cell population proliferation	Mu-type opioid receptor	Homo sapiens (human)
sensory perception of pain	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
behavioral response to ethanol	Mu-type opioid receptor	Homo sapiens (human)
positive regulation of neurogenesis	Mu-type opioid receptor	Homo sapiens (human)
negative regulation of Wnt protein secretion	Mu-type opioid receptor	Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascade	Mu-type opioid receptor	Homo sapiens (human)
calcium ion transmembrane transport	Mu-type opioid receptor	Homo sapiens (human)
cellular response to morphine	Mu-type opioid receptor	Homo sapiens (human)
regulation of cellular response to stress	Mu-type opioid receptor	Homo sapiens (human)
regulation of NMDA receptor activity	Mu-type opioid receptor	Homo sapiens (human)
neuropeptide signaling pathway	Mu-type opioid receptor	Homo sapiens (human)
immune response	Kappa-type opioid receptor	Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway	Kappa-type opioid receptor	Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathway	Kappa-type opioid receptor	Homo sapiens (human)
chemical synaptic transmission	Kappa-type opioid receptor	Homo sapiens (human)
sensory perception	Kappa-type opioid receptor	Homo sapiens (human)
locomotory behavior	Kappa-type opioid receptor	Homo sapiens (human)
sensory perception of pain	Kappa-type opioid receptor	Homo sapiens (human)
adenylate cyclase-inhibiting opioid receptor signaling pathway	Kappa-type opioid receptor	Homo sapiens (human)
response to insulin	Kappa-type opioid receptor	Homo sapiens (human)
positive regulation of dopamine secretion	Kappa-type opioid receptor	Homo sapiens (human)
negative regulation of luteinizing hormone secretion	Kappa-type opioid receptor	Homo sapiens (human)
response to nicotine	Kappa-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor signaling pathway	Kappa-type opioid receptor	Homo sapiens (human)
maternal behavior	Kappa-type opioid receptor	Homo sapiens (human)
eating behavior	Kappa-type opioid receptor	Homo sapiens (human)
response to estrogen	Kappa-type opioid receptor	Homo sapiens (human)
estrous cycle	Kappa-type opioid receptor	Homo sapiens (human)
response to ethanol	Kappa-type opioid receptor	Homo sapiens (human)
regulation of saliva secretion	Kappa-type opioid receptor	Homo sapiens (human)
behavioral response to cocaine	Kappa-type opioid receptor	Homo sapiens (human)
sensory perception of temperature stimulus	Kappa-type opioid receptor	Homo sapiens (human)
defense response to virus	Kappa-type opioid receptor	Homo sapiens (human)
cellular response to lipopolysaccharide	Kappa-type opioid receptor	Homo sapiens (human)
cellular response to glucose stimulus	Kappa-type opioid receptor	Homo sapiens (human)
positive regulation of p38MAPK cascade	Kappa-type opioid receptor	Homo sapiens (human)
positive regulation of potassium ion transmembrane transport	Kappa-type opioid receptor	Homo sapiens (human)
response to acrylamide	Kappa-type opioid receptor	Homo sapiens (human)
positive regulation of eating behavior	Kappa-type opioid receptor	Homo sapiens (human)
conditioned place preference	Kappa-type opioid receptor	Homo sapiens (human)
neuropeptide signaling pathway	Kappa-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
monooxygenase activity	Cytochrome P450 2D6	Homo sapiens (human)
iron ion binding	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity	Cytochrome P450 2D6	Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	Cytochrome P450 2D6	Homo sapiens (human)
heme binding	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 8,9 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 11,12 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
anandamide 14,15 epoxidase activity	Cytochrome P450 2D6	Homo sapiens (human)
protein binding	Alpha-1D adrenergic receptor	Homo sapiens (human)
identical protein binding	Alpha-1D adrenergic receptor	Homo sapiens (human)
alpha1-adrenergic receptor activity	Alpha-1D adrenergic receptor	Homo sapiens (human)
G-protein alpha-subunit binding	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled receptor activity	Mu-type opioid receptor	Homo sapiens (human)
beta-endorphin receptor activity	Mu-type opioid receptor	Homo sapiens (human)
voltage-gated calcium channel activity	Mu-type opioid receptor	Homo sapiens (human)
protein binding	Mu-type opioid receptor	Homo sapiens (human)
morphine receptor activity	Mu-type opioid receptor	Homo sapiens (human)
G-protein beta-subunit binding	Mu-type opioid receptor	Homo sapiens (human)
neuropeptide binding	Mu-type opioid receptor	Homo sapiens (human)
G protein-coupled opioid receptor activity	Kappa-type opioid receptor	Homo sapiens (human)
protein binding	Kappa-type opioid receptor	Homo sapiens (human)
receptor serine/threonine kinase binding	Kappa-type opioid receptor	Homo sapiens (human)
dynorphin receptor activity	Kappa-type opioid receptor	Homo sapiens (human)
neuropeptide binding	Kappa-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
mitochondrion	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum	Cytochrome P450 2D6	Homo sapiens (human)
endoplasmic reticulum membrane	Cytochrome P450 2D6	Homo sapiens (human)
cytoplasm	Cytochrome P450 2D6	Homo sapiens (human)
intracellular membrane-bounded organelle	Cytochrome P450 2D6	Homo sapiens (human)
plasma membrane	Alpha-1D adrenergic receptor	Homo sapiens (human)
plasma membrane	Alpha-1D adrenergic receptor	Homo sapiens (human)
endosome	Mu-type opioid receptor	Homo sapiens (human)
endoplasmic reticulum	Mu-type opioid receptor	Homo sapiens (human)
Golgi apparatus	Mu-type opioid receptor	Homo sapiens (human)
plasma membrane	Mu-type opioid receptor	Homo sapiens (human)
axon	Mu-type opioid receptor	Homo sapiens (human)
dendrite	Mu-type opioid receptor	Homo sapiens (human)
perikaryon	Mu-type opioid receptor	Homo sapiens (human)
synapse	Mu-type opioid receptor	Homo sapiens (human)
plasma membrane	Mu-type opioid receptor	Homo sapiens (human)
neuron projection	Mu-type opioid receptor	Homo sapiens (human)
nucleoplasm	Kappa-type opioid receptor	Homo sapiens (human)
mitochondrion	Kappa-type opioid receptor	Homo sapiens (human)
cytosol	Kappa-type opioid receptor	Homo sapiens (human)
plasma membrane	Kappa-type opioid receptor	Homo sapiens (human)
membrane	Kappa-type opioid receptor	Homo sapiens (human)
sarcoplasmic reticulum	Kappa-type opioid receptor	Homo sapiens (human)
T-tubule	Kappa-type opioid receptor	Homo sapiens (human)
dendrite	Kappa-type opioid receptor	Homo sapiens (human)
synaptic vesicle membrane	Kappa-type opioid receptor	Homo sapiens (human)
presynaptic membrane	Kappa-type opioid receptor	Homo sapiens (human)
perikaryon	Kappa-type opioid receptor	Homo sapiens (human)
axon terminus	Kappa-type opioid receptor	Homo sapiens (human)
postsynaptic membrane	Kappa-type opioid receptor	Homo sapiens (human)
plasma membrane	Kappa-type opioid receptor	Homo sapiens (human)
neuron projection	Kappa-type opioid receptor	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (90)

Assay ID	Title	Year	Journal	Article
AID1775342	Stability of the compound in water-methanol mixture (1:1) assessed as drug recovery	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID222594	Effect of Corynantheidine (10 uM) on twitch contraction inhibited by Verapamil (3 uM) in guinea pig	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1830051	Displacement of [125I](+/-)DOI from human recombinant 5-HT2B receptor expressed in CHO cells at 100 nM measured after 60 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1830047	Displacement of [3H]BRL43694 from human recombinant 5-HT3 receptor expressed in CHO cells at 100 nM measured after 120 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1581707	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1A receptor expressed in CHO cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1830049	Displacement of [125I](+/-)DOI from human recombinant 5-HT2C receptor expressed in CHO cells at 100 nM measured after 60 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID222419	Relative inhibitory activity expressed as the percentage of the maximum inhibition by the compound against that of morphine	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1749821	Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in HEK293 cells incubated for 120 mins by radiometric scintillation analysis
AID1581729	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1B receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID222593	Effect of Corynantheidine (10 uM) on twitch contraction inhibited by Atropine (0.1 uM) in guinea pig	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1581709	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1D receptor expressed in CHO cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775285	Dose normalized AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775340	Dose normalized AUC(0-24 hrs) in po dosed rat plasma	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775308	Dose normalized Cmax in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1385454	Cytotoxicity against human HeLa cells assessed as reduction in cell viability at 100 uM after 24 hrs by MTT assay	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe.
AID1830050	Displacement of [125I](+/-)DOI from human recombinant 5-HT2B receptor expressed in CHO cells at 10 uM measured after 60 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1775292	Tmax in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581753	Fraction unbound in human liver microsomes at 1 uM by equilibrium dialysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581728	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1A receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775341	Stability of the compound in rat plasma assessed as drug recovery	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581750	Metabolic stability in human liver microsomes assessed as elimination rate constant in presence of NADPH incubated up to 60 mins by UPLC-MS/MS analysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775339	Dose normalized Cmax in po dosed rat plasma	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID150056	Binding affinity using guinea pig brain membrane preparations, towards Opioid receptor delta 1 using [3H]DPDPE as radioligand	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1775275	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 2.5 ng/ml measured on the bench-top for 2 hrs by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775291	Cmax in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1830035	Displacement of [125I]CYP from rat cerebral cortex 5-HT1B receptor at 100 nM measured after 120 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1581722	Displacement of [3H]U69,593 from human recombinant kappa opioid receptor expressed in rat RBL cell membranes at 1000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581715	Displacement of radioligand from ORL1 (unknown origin) at 100 nM incubated for 120 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581727	Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in HEK293 cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581733	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2C receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581732	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2B receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID222595	Effect of Corynantheidine (10 uM) on twitch contraction inhibited by morphine (1 uM) in guinea pig (P<0.001)	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1385451	Cytotoxicity against human MCF7 cells assessed as reduction in cell viability at 100 uM after 24 hrs by MTT assay	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe.
AID1830052	Displacement of [125I](+/-)DOI from human recombinant 5-HT2A receptor expressed in HEK293 cells at 10 uM measured after 60 to 90 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID149845	Binding affinity using guinea pig brain membrane preparations, towards Opioid receptor kappa 1 using [3H]- U-69,593 as radioligand	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1775282	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 2.5 ng/ml measured at -80 degC for 4 weeks by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581730	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1D receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581720	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2B receptor expressed in CHO cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID149837	Relative affinity evaluated for Opioid receptor kappa 1	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1581716	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1A receptor expressed in CHO cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775278	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 2.5 ng/ml measured in autosampler for 24 hrs by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581717	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1B receptor expressed in CHO cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581710	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2A receptor expressed in CHO cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775280	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 2.5 ng/ml measured under freeze-thaw conditions for 3 cycles by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581724	Displacement of radioligand from ORL1 (unknown origin) at 10000 nM incubated for 120 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID222409	% maximum inhibition is elicited when the response reaches plateau, calculated regarding electrically induced contraction in guinea pig ileum as 100% (P<0.001)	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1581714	Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in HEK293 cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID148204	Binding affinity using guinea pig brain membrane preparations, towards Opioid receptor mu 1 using [3H]- DAMGO as radioligand	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1581726	Displacement of [3H]U69,593 from human recombinant kappa opioid receptor expressed in rat RBL cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1830053	Displacement of [125I](+/-)DOI from human recombinant 5-HT2A receptor expressed in HEK293 cells at 100 nM measured after 60 to 90 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1830033	Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed in cells at 100 nM measured after 60 to 90 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1581755	Metabolic stability in human liver microsomes assessed as hepatic clearance in presence of NADPH incubated up to 60 mins by UPLC-MS/MS analysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581754	Metabolic stability in human liver microsomes assessed as intrinsic clearance in presence of NADPH incubated up to 60 mins by UPLC-MS/MS analysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1830046	Displacement of [3H]BRL43694 from human recombinant 5-HT3 receptor expressed in CHO cells at 10 uM measured after 120 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1775289	Dose normalized Cmax in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1830048	Displacement of [125I](+/-)DOI from human recombinant 5-HT2C receptor expressed in CHO cells at 10 uM measured after 60 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1581752	Fraction unbound in human plasma at 1 uM by equilibrium dialysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID150051	Relative affinity evaluated for Opioid receptor delta 1	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1581721	Displacement of [3H]DADLE from human recombinant delta opioid receptor expressed in rat Chem-1 (RBL) cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581719	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2A receptor expressed in CHO cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581708	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1B receptor expressed in CHO cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581711	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2B receptor expressed in CHO cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581756	Metabolic stability in human liver microsomes assessed as hepatic extraction ratio in presence of NADPH incubated up to 60 mins by UPLC-MS/MS analysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID148190	Relative affinity evaluated for Opioid receptor mu 1	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1775306	Inhibition of CYP2D6 in human liver microsomes assessed as inhibition of dextromethorphan O-demethylation using dextromethorphan as substrate preincubated for 5 mins followed by NADPH addition by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775277	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 160 ng/ml measured on the bench-top for 2 hrs by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID222596	Effect of Corynantheidine (1 uM) on twitch contraction inhibited by Atropine (0.1 uM) in guinea pig	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1775283	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 160 ng/ml measured at -80 degC for 4 weeks by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID222592	Effect of Corynantheidine (1 uM) on twitch contraction inhibited by morphine (1 uM) in guinea pig (P<0.05)	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID1385453	Cytotoxicity against human HT-29 cells assessed as reduction in cell viability at 100 uM after 24 hrs by MTT assay	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe.
AID1775284	Tmax in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775309	Dose normalized AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775290	AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581712	Displacement of [3H]DADLE from human recombinant delta opioid receptor expressed in rat Chem-1 (RBL) cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1830032	Displacement of [125I]CYP from rat cerebral cortex 5-HT1B receptor at 10 uM measured after 120 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
AID1581718	Displacement of [3H]prazosin from human recombinant adrenergic alpha-1D receptor expressed in CHO cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581731	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2A receptor expressed in CHO cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1581751	Metabolic stability in human liver microsomes assessed as half life in presence of NADPH incubated up to 60 mins by UPLC-MS/MS analysis	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1385452	Cytotoxicity against human HepG2 cells assessed as reduction in cell viability at 100 uM after 24 hrs by MTT assay	2018	Journal of natural products, 08-24, Volume: 81, Issue:8	Alkaloids with Immunosuppressive Activity from the Bark of Pausinystalia yohimbe.
AID1775274	Cmax in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581723	Displacement of [3H]DAMGO from human recombinant mu opioid receptor expressed in HEK293 cell membranes at 10000 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775281	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 160 ng/ml measured under freeze-thaw conditions for 3 cycles by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581725	Displacement of [3H]DADLE from human recombinant delta opioid receptor expressed in rat Chem-1 (RBL) cell membranes incubated for 60 mins	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1775279	Stability of the compound in rat plasma assessed as proportion of compound deviation from nominal concentration at 160 ng/ml measured in autosampler for 24 hrs by UPLC-MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID222597	Effect of Corynantheidine (1 uM) on twitch contraction inhibited by Verapamil (3 uM) in guinea pig	2002	Journal of medicinal chemistry, Apr-25, Volume: 45, Issue:9	Studies on the synthesis and opioid agonistic activities of mitragynine-related indole alkaloids: discovery of opioid agonists structurally different from other opioid ligands.
AID397122	Inhibition of HIV1 RT
AID1775307	AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation measured for 24 hrs by UPLC-MS/MS analysis	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1775310	Ratio of Dose normalized AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.18 mg/kg, po administered as OPMS liquid formulation to Dose normalized AUC(0 to 24 hrs) in Sprague-Dawley rat plasma at 0.13 mg/kg, po administered as LKT formulation	2021	Journal of natural products, 04-23, Volume: 84, Issue:4	Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats.
AID1581713	Displacement of [3H]U69,593 from human recombinant kappa opioid receptor expressed in rat RBL cell membranes at 100 nM incubated for 60 mins relative to control	2020	Journal of medicinal chemistry, 01-09, Volume: 63, Issue:1	Investigation of the Adrenergic and Opioid Binding Affinities, Metabolic Stability, Plasma Protein Binding Properties, and Functional Effects of Selected Indole-Based Kratom Alkaloids.
AID1830034	Displacement of [3H]8-OH-DAPT from human recombinant 5-HT1A receptor expressed in cells at 10 uM measured after 60 to 90 mins by radioligand completion assay relative to control	2021	Journal of medicinal chemistry, 09-23, Volume: 64, Issue:18	Activity of
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	1 (16.67)	29.6817
2010's	1 (16.67)	24.3611
2020's	4 (66.67)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	7 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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	2.31	1	phenols; tertiary amino compound; tetralins	serotonergic antagonist
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	2.01	1	aromatic ether; nitrile; polyether; tertiary amino compound
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	2.25	1	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
prazosin Prazosin: A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.. prazosin : A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.	2.25	1	aromatic ether; furans; monocarboxylic acid amide; piperazines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor
sb 206553 SB 206553: a high-affinity 5-HT(2C/2B) antagonist; structure given in first source	2.31	1	pyrroloindole
n-(2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)-n-(2-pyridinyl)cyclohexanecarboxamide [no description available]	2.31	1	piperazines
wb 4101 N-(2,3-dihydro-1,4-benzodioxin-2-ylmethyl)-2-(2,6-dimethoxyphenoxy)ethanamine : A benzodioxine that is 2,3-dihydro-1,4-benzodioxine bearing a [(2',6'-dimethoxyphenoxy)ethylamino]methyl group at position 2. An alpha1A-adrenergic selective antagonist.	2.25	1	aromatic ether; benzodioxine; secondary amino compound	alpha-adrenergic antagonist
yohimbine Yohimbine: A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.. yohimbine : An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.	2.25	1	methyl 17-hydroxy-20xi-yohimban-16-carboxylate	alpha-adrenergic antagonist; dopamine receptor D2 antagonist; serotonergic antagonist
ipsapirone [no description available]	2.31	1	N-arylpiperazine
corynanthine Corynanthine: A stereoisomer of yohimbine.	2.17	1	yohimban alkaloid
mitraphylline mitraphylline: isolated from Uncaria tomentosa	2.31	1	indolizines
enkephalin, d-penicillamine (2,5)- Enkephalin, D-Penicillamine (2,5)-: A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity.. DPDPE : A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond.	2.25	1	heterodetic cyclic peptide	delta-opioid receptor agonist
u 69593 U 69593: selective ligand for opioid K-receptor. U69593 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of phenylacetic acid and the secodary amino group of (5R,7S,8S)-N-methyl-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]decan-8-amine.	2.25	1	monocarboxylic acid amide; N-alkylpyrrolidine; organic heterobicyclic compound; oxaspiro compound	anti-inflammatory agent; diuretic; kappa-opioid receptor agonist
atropine tropan-3alpha-yl 3-hydroxy-2-phenylpropanoate : A tropane alkaloid that is (1R,5)-8-methyl-8-azabicyclo[3.2.1]octane substituted by a (3-hydroxy-2-phenylpropanoyl)oxy group at position 3.	2.01	1
mitragynine [no description available]	3.04	4	monoterpenoid indole alkaloid
u-50488 3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer: A non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE. (From J Pharmacol Exp Ther 1997;280(1):416-21). U50488 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of 3,4-dichlorophenylacetic acid and the secondary amino group of (1R,2R)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine	2.25	1	dichlorobenzene; monocarboxylic acid amide; N-alkylpyrrolidine	analgesic; antitussive; calcium channel blocker; diuretic; kappa-opioid receptor agonist
paynantheine paynantheine: structure in first source	2.72	2
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	2.47	2	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
enkephalin, ala(2)-mephe(4)-gly(5)- [no description available]	2.25	1	peptide
4-iodo-2,5-dimethoxyphenylisopropylamine, (r)-isomer [no description available]	2.31	1
corynoxine b corynoxine B: structure in first source	2.63	2	indolizines	metabolite
corynoxine corynoxine: structure in first source	2.63	2	indolizines	metabolite
mitragynine, (3beta,16e,20beta)-isomer [no description available]	2.98	3
mitragynine speciogynine: structure in first source	2.72	2
7-hydroxymitragynine 7-hydroxymitragynine: an orally active opioid analgesic from the Thai medicinal herb Mitragyna speciosa; structure in first source	3.04	4	alkaloid
mitragynine pseudoindoxyl mitragynine pseudoindoxyl: derived from Thai medicinal plant MITRAGYNA speciosa; opioid agonist	2.01	1
corynoxeine corynoxeine: active principles of Uncariae Ramulus et Uncus; structure given in first source for ((7beta,16E,20alpha)-isomer) and ((16E,20alpha)-isomer); RN given refers to ((7beta,16E,20alpha)-isomer)	2.17	1

Condition	Indicated	Relationship Strength	Studies	Trials
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.	0	2.01	1	0
Nociceptive Pain Dull or sharp aching pain caused by stimulated NOCICEPTORS due to tissue injury, inflammation or diseases. It can be divided into somatic or tissue pain and VISCERAL PAIN.	0	2.31	1	0

hirsutine, (16e,20beta)-isomer

Cross-References

Synonyms (23)

Roles (1)

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Biological Processes (66)

Molecular Functions (21)

Ceullar Components (22)

Bioassays (90)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.89

Study Types

hirsutine, (16e,20beta)-isomer

Cross-References

Synonyms (23)

Roles (1)

Drug Classes (1)

Protein Targets (4)

Inhibition Measurements

Biological Processes (66)

Molecular Functions (21)

Ceullar Components (22)

Bioassays (90)

Research

Studies (6)

Market Indicators

Research Demand Index: 12.89

Study Types

Related Drugs (27)

Related Conditions (2)