Page last updated: 2024-12-11

1-methyl-d-lysergic acid butanolamide

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

You're asking about **1-methyl-D-lysergic acid butanolamide (1-Me-LSD-BA)**. This is a synthetic compound, a close chemical relative of the well-known psychedelic drug LSD (lysergic acid diethylamide).

**Here's what makes it interesting for research:**

* **Unique Properties:** 1-Me-LSD-BA shares some structural similarities with LSD, but its effects and pharmacological profile are distinct. This makes it a valuable tool for studying how subtle chemical changes in psychedelic compounds influence their interactions with the brain.
* **Potential Therapeutic Applications:** While LSD is known for its psychedelic effects, research suggests that 1-Me-LSD-BA might exhibit different and possibly beneficial effects. This includes:
* **Anti-inflammatory properties:** Some studies suggest it may have anti-inflammatory activity, which could be relevant for treating various inflammatory conditions.
* **Neuroprotective effects:** Research indicates it might offer neuroprotection, potentially shielding brain cells from damage.
* **Anxiolytic potential:** Some studies point to potential anxiolytic (anxiety-reducing) effects.

**Research Focus Areas:**

* **Understanding its mechanism of action:** Scientists are investigating how 1-Me-LSD-BA interacts with receptors in the brain, specifically serotonin receptors. This research helps us understand its effects and potentially identify new targets for therapeutic development.
* **Exploring its therapeutic potential:** Researchers are conducting studies to investigate its potential use in treating conditions like inflammation, neurodegenerative disorders, and anxiety.
* **Comparing its effects to LSD:** Researchers aim to understand how 1-Me-LSD-BA differs from LSD in terms of its effects and duration of action.

**It's important to note:** 1-Me-LSD-BA is still a relatively new compound with limited research data. More studies are needed to fully understand its safety, effectiveness, and potential for therapeutic applications.

**Disclaimer:** I am an AI chatbot and cannot provide medical advice. Information about pharmaceuticals should always be obtained from qualified healthcare professionals.

Cross-References

ID SourceID
PubMed CID6540428
CHEMBL ID485253
CHEBI ID584020
SCHEMBL ID467883
MeSH IDM0107466

Synonyms (24)

Synonym
methysergidum [inn-latin]
n-(alpha-(hydroxymethyl)propyl)-1-methyl-dextro-lysergamide
metisergide [dcit]
metisergido [inn-spanish]
9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
(+)-9,10-didehydro-n-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
n-(1-(hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
(+)-n-(1-(hydroxymethyl)propyl)-1-methyl-d-lysergamide
1-methylmethylergonovine
DB00247
1-methyl-d-lysergic acid butanolamide
1-methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
(8r)-n-[1-hydroxymethyl(propyl)]-1,6-dimethyl-9,10-didehydroergoline-8-carboxamide
CHEBI:584020 ,
metisergida
methysergidum
CHEMBL485253
SCHEMBL467883
bdbm50469883
220756-57-0
(6ar,9r)-n-(1-hydroxy-2-butanyl)-4,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
DTXSID10859349
(4r,7r)-n-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
EN300-33419388

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Human oral bioavailability is an important pharmacokinetic property, which is directly related to the amount of drug available in the systemic circulation to exert pharmacological and therapeutic effects."( Hologram QSAR model for the prediction of human oral bioavailability.
Andricopulo, AD; Moda, TL; Montanari, CA, 2007
)
0.34

Dosage Studied

ExcerptRelevanceReference
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
serotonergic antagonistDrugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
sympatholytic agentAny compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
vasoconstrictor agentDrug used to cause constriction of the blood vessels.
[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 (2)

ClassDescription
monocarboxylic acid amideA carboxamide derived from a monocarboxylic acid.
ergot alkaloid
[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 (8)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Bile salt export pumpHomo sapiens (human)IC50 (µMol)33.07000.11007.190310.0000AID1449628
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki0.00180.00010.601710.0000AID5342; AID5581
Endothelin receptor type BRattus norvegicus (Norway rat)Ki0.01260.00630.05750.3710AID6685
Endothelin receptor type BHomo sapiens (human)Ki0.01260.00010.05430.3710AID6670; AID6685
5-hydroxytryptamine receptor 2AHomo sapiens (human)Ki0.00160.00000.385510.0000AID707294
5-hydroxytryptamine receptor 7 Rattus norvegicus (Norway rat)Ki0.01260.00000.14803.1800AID6670
5-hydroxytryptamine receptor 7Homo sapiens (human)Ki0.04600.00030.380610.0000AID1546005; AID6685
Sigma non-opioid intracellular receptor 1Homo sapiens (human)IC50 (µMol)0.91200.00030.70285.3660AID203852
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (118)

Processvia Protein(s)Taxonomy
fatty acid metabolic processBile salt export pumpHomo sapiens (human)
bile acid biosynthetic processBile salt export pumpHomo sapiens (human)
xenobiotic metabolic processBile salt export pumpHomo sapiens (human)
xenobiotic transmembrane transportBile salt export pumpHomo sapiens (human)
response to oxidative stressBile salt export pumpHomo sapiens (human)
bile acid metabolic processBile salt export pumpHomo sapiens (human)
response to organic cyclic compoundBile salt export pumpHomo sapiens (human)
bile acid and bile salt transportBile salt export pumpHomo sapiens (human)
canalicular bile acid transportBile salt export pumpHomo sapiens (human)
protein ubiquitinationBile salt export pumpHomo sapiens (human)
regulation of fatty acid beta-oxidationBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transportBile salt export pumpHomo sapiens (human)
bile acid signaling pathwayBile salt export pumpHomo sapiens (human)
cholesterol homeostasisBile salt export pumpHomo sapiens (human)
response to estrogenBile salt export pumpHomo sapiens (human)
response to ethanolBile salt export pumpHomo sapiens (human)
xenobiotic export from cellBile salt export pumpHomo sapiens (human)
lipid homeostasisBile salt export pumpHomo sapiens (human)
phospholipid homeostasisBile salt export pumpHomo sapiens (human)
positive regulation of bile acid secretionBile salt export pumpHomo sapiens (human)
regulation of bile acid metabolic processBile salt export pumpHomo sapiens (human)
transmembrane transportBile salt export pumpHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIEndothelin receptor type BHomo sapiens (human)
neural crest cell migrationEndothelin receptor type BHomo sapiens (human)
positive regulation of protein phosphorylationEndothelin receptor type BHomo sapiens (human)
renin secretion into blood streamEndothelin receptor type BHomo sapiens (human)
regulation of heart rateEndothelin receptor type BHomo sapiens (human)
regulation of pHEndothelin receptor type BHomo sapiens (human)
cell surface receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
negative regulation of adenylate cyclase activityEndothelin receptor type BHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
positive regulation of cytosolic calcium ion concentrationEndothelin receptor type BHomo sapiens (human)
nervous system developmentEndothelin receptor type BHomo sapiens (human)
peripheral nervous system developmentEndothelin receptor type BHomo sapiens (human)
posterior midgut developmentEndothelin receptor type BHomo sapiens (human)
positive regulation of cell population proliferationEndothelin receptor type BHomo sapiens (human)
gene expressionEndothelin receptor type BHomo sapiens (human)
negative regulation of neuron maturationEndothelin receptor type BHomo sapiens (human)
response to organic cyclic compoundEndothelin receptor type BHomo sapiens (human)
vein smooth muscle contractionEndothelin receptor type BHomo sapiens (human)
calcium-mediated signalingEndothelin receptor type BHomo sapiens (human)
cGMP-mediated signalingEndothelin receptor type BHomo sapiens (human)
heparin metabolic processEndothelin receptor type BHomo sapiens (human)
melanocyte differentiationEndothelin receptor type BHomo sapiens (human)
regulation of fever generationEndothelin receptor type BHomo sapiens (human)
aldosterone metabolic processEndothelin receptor type BHomo sapiens (human)
enteric smooth muscle cell differentiationEndothelin receptor type BHomo sapiens (human)
positive regulation of urine volumeEndothelin receptor type BHomo sapiens (human)
renal sodium excretionEndothelin receptor type BHomo sapiens (human)
epithelial fluid transportEndothelin receptor type BHomo sapiens (human)
vasoconstrictionEndothelin receptor type BHomo sapiens (human)
vasodilationEndothelin receptor type BHomo sapiens (human)
negative regulation of apoptotic processEndothelin receptor type BHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionEndothelin receptor type BHomo sapiens (human)
macrophage chemotaxisEndothelin receptor type BHomo sapiens (human)
response to painEndothelin receptor type BHomo sapiens (human)
enteric nervous system developmentEndothelin receptor type BHomo sapiens (human)
regulation of epithelial cell proliferationEndothelin receptor type BHomo sapiens (human)
negative regulation of protein metabolic processEndothelin receptor type BHomo sapiens (human)
canonical Wnt signaling pathwayEndothelin receptor type BHomo sapiens (human)
positive regulation of penile erectionEndothelin receptor type BHomo sapiens (human)
establishment of endothelial barrierEndothelin receptor type BHomo sapiens (human)
renal sodium ion absorptionEndothelin receptor type BHomo sapiens (human)
calcium ion transmembrane transportEndothelin receptor type BHomo sapiens (human)
cellular response to lipopolysaccharideEndothelin receptor type BHomo sapiens (human)
protein transmembrane transportEndothelin receptor type BHomo sapiens (human)
podocyte differentiationEndothelin receptor type BHomo sapiens (human)
endothelin receptor signaling pathwayEndothelin receptor type BHomo sapiens (human)
renal albumin absorptionEndothelin receptor type BHomo sapiens (human)
neuroblast migrationEndothelin receptor type BHomo sapiens (human)
chordate pharynx developmentEndothelin receptor type BHomo sapiens (human)
response to sodium phosphateEndothelin receptor type BHomo sapiens (human)
response to endothelinEndothelin receptor type BHomo sapiens (human)
developmental pigmentationEndothelin receptor type BHomo sapiens (human)
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)
smooth muscle contraction5-hydroxytryptamine receptor 7Homo sapiens (human)
circadian rhythm5-hydroxytryptamine receptor 7Homo sapiens (human)
blood circulation5-hydroxytryptamine receptor 7Homo sapiens (human)
vasoconstriction5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled serotonin receptor signaling pathway5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 7Homo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 7Homo sapiens (human)
lipid transportSigma non-opioid intracellular receptor 1Homo sapiens (human)
nervous system developmentSigma non-opioid intracellular receptor 1Homo sapiens (human)
G protein-coupled opioid receptor signaling pathwaySigma non-opioid intracellular receptor 1Homo sapiens (human)
regulation of neuron apoptotic processSigma non-opioid intracellular receptor 1Homo sapiens (human)
protein homotrimerizationSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (21)

Processvia Protein(s)Taxonomy
protein bindingBile salt export pumpHomo sapiens (human)
ATP bindingBile salt export pumpHomo sapiens (human)
ABC-type xenobiotic transporter activityBile salt export pumpHomo sapiens (human)
bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
canalicular bile acid transmembrane transporter activityBile salt export pumpHomo sapiens (human)
carbohydrate transmembrane transporter activityBile salt export pumpHomo sapiens (human)
ABC-type bile acid transporter activityBile salt export pumpHomo sapiens (human)
ATP hydrolysis activityBile salt export pumpHomo sapiens (human)
endothelin receptor activityEndothelin receptor type BHomo sapiens (human)
protein bindingEndothelin receptor type BHomo sapiens (human)
peptide hormone bindingEndothelin receptor type BHomo sapiens (human)
type 1 angiotensin receptor bindingEndothelin receptor type BHomo sapiens (human)
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)
protein binding5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 7Homo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 7Homo sapiens (human)
G protein-coupled opioid receptor activitySigma non-opioid intracellular receptor 1Homo sapiens (human)
protein bindingSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (38)

Processvia Protein(s)Taxonomy
basolateral plasma membraneBile salt export pumpHomo sapiens (human)
Golgi membraneBile salt export pumpHomo sapiens (human)
endosomeBile salt export pumpHomo sapiens (human)
plasma membraneBile salt export pumpHomo sapiens (human)
cell surfaceBile salt export pumpHomo sapiens (human)
apical plasma membraneBile salt export pumpHomo sapiens (human)
intercellular canaliculusBile salt export pumpHomo sapiens (human)
intracellular canaliculusBile salt export pumpHomo sapiens (human)
recycling endosomeBile salt export pumpHomo sapiens (human)
recycling endosome membraneBile salt export pumpHomo sapiens (human)
extracellular exosomeBile salt export pumpHomo sapiens (human)
membraneBile salt export pumpHomo sapiens (human)
plasma membraneEndothelin receptor type BHomo sapiens (human)
nuclear membraneEndothelin receptor type BHomo sapiens (human)
plasma membraneEndothelin receptor type BHomo sapiens (human)
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)
plasma membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
trans-Golgi network membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
synapse5-hydroxytryptamine receptor 7Homo sapiens (human)
dendrite5-hydroxytryptamine receptor 7Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 7Homo sapiens (human)
nuclear envelopeSigma non-opioid intracellular receptor 1Homo sapiens (human)
nuclear inner membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
nuclear outer membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulumSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulum membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
lipid dropletSigma non-opioid intracellular receptor 1Homo sapiens (human)
cytosolSigma non-opioid intracellular receptor 1Homo sapiens (human)
postsynaptic densitySigma non-opioid intracellular receptor 1Homo sapiens (human)
membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
growth coneSigma non-opioid intracellular receptor 1Homo sapiens (human)
cytoplasmic vesicleSigma non-opioid intracellular receptor 1Homo sapiens (human)
anchoring junctionSigma non-opioid intracellular receptor 1Homo sapiens (human)
postsynaptic density membraneSigma non-opioid intracellular receptor 1Homo sapiens (human)
endoplasmic reticulumSigma non-opioid intracellular receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (91)

Assay IDTitleYearJournalArticle
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID625284Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic failure2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID707297Displacement of [3H]ketanserin from human 5HT2AR expressed in CHOK1 cells at 0.1 uM2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Discovery and pharmacological profile of new 1H-indazole-3-carboxamide and 2H-pyrrolo[3,4-c]quinoline derivatives as selective serotonin 4 receptor ligands.
AID496823Antimicrobial activity against Trichomonas vaginalis2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID205269Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM1985Journal of medicinal chemistry, Mar, Volume: 28, Issue:3
[3H]Batrachotoxinin A 20 alpha-benzoate binding to voltage-sensitive sodium channels: a rapid and quantitative assay for local anesthetic activity in a variety of drugs.
AID625285Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatic necrosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID196752Compound was evaluated for its activity at membrane-bound receptor (M+L+P fraction) from rat frontal cortex1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
In vitro labeling of serotonin-S2 receptors: synthesis and binding characteristics of [3H]-7-aminoketanserin.
AID337898Displacement of [3H]ketanserin from 5HT2 receptor1993Journal of natural products, Apr, Volume: 56, Issue:4
The role of receptor binding in drug discovery.
AID685502HARVARD: Inhibition of blood stage Plasmodium falciparum 3D7 infection2012Proceedings of the National Academy of Sciences of the United States of America, May-29, Volume: 109, Issue:22
Liver-stage malaria parasites vulnerable to diverse chemical scaffolds.
AID625290Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver fatty2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID3701Tested for 5-hydroxytryptamine 1 receptor binding ability by displacement of [3H]5-HT from rat brain synaptosomes1987Journal of medicinal chemistry, Dec, Volume: 30, Issue:12
Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogues.
AID732420Efflux ratio of permeability from basolateral to apical side over apical to basolateral in pig LLC-PK1 cells overexpressing human MDR1 relative to efflux ratio in parental cell line2013ACS medicinal chemistry letters, Jan-10, Volume: 4, Issue:1
De novo prediction of p-glycoprotein-mediated efflux liability for druglike compounds.
AID496828Antimicrobial activity against Leishmania donovani2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID203852The compound was tested for affinity towards sigma-3 receptor1994Journal of medicinal chemistry, Nov-25, Volume: 37, Issue:24
Conformational analysis, pharmacophore identification, and comparative molecular field analysis of ligands for the neuromodulatory sigma 3 receptor.
AID496831Antimicrobial activity against Cryptosporidium parvum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID5072Tested for 5-hydroxytryptamine 2 receptor binding ability by displacement of [3H]spiperone from rat brain frontal cortex synaptosomes1987Journal of medicinal chemistry, Dec, Volume: 30, Issue:12
Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogues.
AID625288Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for jaundice2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID625289Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver disease2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID496827Antimicrobial activity against Leishmania amazonensis2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID625280Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholecystitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID6685Non-selective inhibitory activity was determined against 5-hydroxytryptamine 7 receptor2003Journal of medicinal chemistry, Dec-18, Volume: 46, Issue:26
Optimization of the pharmacophore model for 5-HT7R antagonism. Design and synthesis of new naphtholactam and naphthosultam derivatives.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1204336Displacement of [3H]8-OH-DPAT from rat hippocampus 5-HT1A receptor assessed as total radioligand binding at 1.66 x 10'-7 M incubated for 20 mins by microbeta plate reader based method2015European journal of medicinal chemistry, Jun-05, Volume: 97Structure-activity relationships and molecular studies of novel arylpiperazinylalkyl purine-2,4-diones and purine-2,4,8-triones with antidepressant and anxiolytic-like activity.
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID497005Antimicrobial activity against Pneumocystis carinii2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID337595Inhibition of acetylcholine-induced contraction in guinea pig ileum at 0.1 ug/ml1994Journal of natural products, Sep, Volume: 57, Issue:9
(+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.).
AID707294Displacement of [3H]ketanserin from human 5HT2AR expressed in CHOK1 cells2012Journal of medicinal chemistry, Nov-26, Volume: 55, Issue:22
Discovery and pharmacological profile of new 1H-indazole-3-carboxamide and 2H-pyrrolo[3,4-c]quinoline derivatives as selective serotonin 4 receptor ligands.
AID496821Antimicrobial activity against Leishmania2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1204335Displacement of [3H]8-OH-DPAT from rat hippocampus 5-HT1A receptor assessed as total radioligand binding at 1 uM incubated for 20 mins by microbeta plate reader based method2015European journal of medicinal chemistry, Jun-05, Volume: 97Structure-activity relationships and molecular studies of novel arylpiperazinylalkyl purine-2,4-diones and purine-2,4,8-triones with antidepressant and anxiolytic-like activity.
AID337594Inhibition of acetylcholine-induced contraction in guinea pig ileum at 70 ug/ml1994Journal of natural products, Sep, Volume: 57, Issue:9
(+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.).
AID227718Binding energy by using the equation deltaG obsd = -RT ln KD1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Functional group contributions to drug-receptor interactions.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID496818Antimicrobial activity against Trypanosoma brucei brucei2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1546005Displacement of [3H]5-HT from recombinant human 5-HT7 receptor expressed in African green monkey COS7 cells2019European journal of medicinal chemistry, Dec-01, Volume: 183Structure-activity relationships of serotonin 5-HT
AID5249Binding affinity which represents concentration giving half-maximal inhibition of [3H]ketanserin binding to 5-hydroxytryptamine 2 receptor from rat tissue homogenate1998Journal of medicinal chemistry, Sep-24, Volume: 41, Issue:20
New antipsychotic agents with serotonin and dopamine antagonist properties based on a pyrrolo[2,1-b][1,3]benzothiazepine structure.
AID402828Displacement of [3H]ketanserin from 5HT2A receptor in rabbit cerebral cortex membrane1997Journal of natural products, Jun, Volume: 60, Issue:6
Activity of Parthenolide at 5HT2A receptors.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID496824Antimicrobial activity against Toxoplasma gondii2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID5330Inhibition of [3H]ketanserin binding to 5-hydroxytryptamine 2A receptor rat frontal cortex membrane1994Journal of medicinal chemistry, Aug-05, Volume: 37, Issue:16
Synthesis and atypical antipsychotic profile of some 2-(2-piperidinoethyl)benzocycloalkanones as analogues of butyrophenone.
AID225618compound was tested for antagonistic activity against fenfluramine induced hyperthermia in rat after peroral administration; Value ranges from 0.1-1.31987Journal of medicinal chemistry, Dec, Volume: 30, Issue:12
Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogues.
AID685503HARVARD: Inhibition of blood stage Plasmodium falciparum Dd2 infection2012Proceedings of the National Academy of Sciences of the United States of America, May-29, Volume: 109, Issue:22
Liver-stage malaria parasites vulnerable to diverse chemical scaffolds.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID496819Antimicrobial activity against Plasmodium falciparum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID398675Antagonist activity at serotonin receptor in guinea pig ileum assessed as inhibition of serotonin-induced contraction1995Journal of natural products, Aug, Volume: 58, Issue:8
Further brominated bis- and tris-indole alkaloids from the deep-water New Caledonian marine sponge Orina Sp.
AID685501HARVARD: Inhibition of liver stage Plasmodium berghei infection in HepG2 cells2012Proceedings of the National Academy of Sciences of the United States of America, May-29, Volume: 109, Issue:22
Liver-stage malaria parasites vulnerable to diverse chemical scaffolds.
AID496830Antimicrobial activity against Leishmania major2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID496820Antimicrobial activity against Trypanosoma brucei2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID409956Inhibition of mouse brain MAOB2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID496817Antimicrobial activity against Trypanosoma cruzi2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID409954Inhibition of mouse brain MAOA2008Journal of medicinal chemistry, Nov-13, Volume: 51, Issue:21
Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.
AID496826Antimicrobial activity against Entamoeba histolytica2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID5581Binding affinity to 5-hydroxytryptamine 2A receptor from rat cortex assayed using [3H]ketanserin as radioligand.1995Journal of medicinal chemistry, Jul-07, Volume: 38, Issue:14
Novel, potent, and selective 5-HT3 receptor antagonists based on the arylpiperazine skeleton: synthesis, structure, biological activity, and comparative molecular field analysis studies.
AID625283Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for elevated liver function tests2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID625278FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of no concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID311524Oral bioavailability in human2007Bioorganic & medicinal chemistry, Dec-15, Volume: 15, Issue:24
Hologram QSAR model for the prediction of human oral bioavailability.
AID196753Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solubilized preparation) from rat frontal cortex1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
In vitro labeling of serotonin-S2 receptors: synthesis and binding characteristics of [3H]-7-aminoketanserin.
AID225834compound was tested for antagonistic activity against 5-Hydroxytryptamine-induced head shake in mouse after intraperitoneal administration; Value ranges from 0.35-0.771987Journal of medicinal chemistry, Dec, Volume: 30, Issue:12
Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogues.
AID625282Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cirrhosis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID196754Compound was evaluated for its activity at membrane-bound receptor (M+L+P fraction) from rat frontal cortex1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
In vitro labeling of serotonin-S2 receptors: synthesis and binding characteristics of [3H]-7-aminoketanserin.
AID625286Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatitis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID496825Antimicrobial activity against Leishmania mexicana2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID195207The compound was evaluated for the percentage inhibition in rat aorta stimulated with 30 uM 5-HT and tested at fixed concentration of 10 uM1994Journal of medicinal chemistry, Apr-29, Volume: 37, Issue:9
Synthesis of 2-piperazinylbenzothiazole and 2-piperazinylbenzoxazole derivatives with 5-HT3 antagonist and 5-HT4 agonist properties.
AID1449628Inhibition of human BSEP expressed in baculovirus transfected fall armyworm Sf21 cell membranes vesicles assessed as reduction in ATP-dependent [3H]-taurocholate transport into vesicles incubated for 5 mins by Topcount based rapid filtration method2012Drug metabolism and disposition: the biological fate of chemicals, Dec, Volume: 40, Issue:12
Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
AID196755Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solubilized preparation) from rat frontal cortex1986Journal of medicinal chemistry, Sep, Volume: 29, Issue:9
In vitro labeling of serotonin-S2 receptors: synthesis and binding characteristics of [3H]-7-aminoketanserin.
AID625281Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for cholelithiasis2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID5342The compound was tested for the binding affinity against 5-hydroxytryptamine 2A receptor using [3H]ketanserin as radioligand.1999Journal of medicinal chemistry, Oct-21, Volume: 42, Issue:21
Pyrroloquinoxaline derivatives as high-affinity and selective 5-HT(3) receptor agonists: synthesis, further structure-activity relationships, and biological studies.
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID337897Displacement of [3H]5HT from 5HT1 receptor1993Journal of natural products, Apr, Volume: 56, Issue:4
The role of receptor binding in drug discovery.
AID6670Binding affinity towards 5-hydroxytryptamine 7 receptor2000Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10
First pharmacophoric hypothesis for 5-HT7 antagonism.
AID625287Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for hepatomegaly2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID625279Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for bilirubinemia2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID685500HARVARD: Cytotoxicity in HepG2 cell line2012Proceedings of the National Academy of Sciences of the United States of America, May-29, Volume: 109, Issue:22
Liver-stage malaria parasites vulnerable to diverse chemical scaffolds.
AID625292Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) combined score2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID496832Antimicrobial activity against Trypanosoma brucei rhodesiense2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID337593Inhibition of acetylcholine-induced contraction in guinea pig ileum at 6.5 ug/ml1994Journal of natural products, Sep, Volume: 57, Issue:9
(+/-)-Gelliusines A and B, two diastereomeric brominated tris-indole alkaloids from a deep water new caledonian marine sponge (Gellius or Orina sp.).
AID496829Antimicrobial activity against Leishmania infantum2010Bioorganic & medicinal chemistry, Mar-15, Volume: 18, Issue:6
Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID625291Drug Induced Liver Injury Prediction System (DILIps) training set; hepatic side effect (HepSE) score for liver function tests abnormal2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (28)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (14.29)18.7374
1990's10 (35.71)18.2507
2000's4 (14.29)29.6817
2010's10 (35.71)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: 11.52

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.52 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.52)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (10.34%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (89.66%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]