laudanosoline profile

Laudanosoline is a naturally occurring aporphine alkaloid found in various plants, including Papaver somniferum (opium poppy). It exhibits a range of pharmacological activities, including anti-inflammatory, analgesic, and neuroprotective effects. Laudanosoline has been investigated for its potential therapeutic applications in conditions such as Alzheimer's disease, Parkinson's disease, and pain management. Research into laudanosoline focuses on understanding its mechanisms of action, exploring its therapeutic potential, and optimizing its pharmacological properties. Studies have shown that laudanosoline can interact with various targets, including G-protein coupled receptors, ion channels, and enzymes. Its synthesis involves complex biosynthetic pathways within the plant, and synthetic approaches have also been developed to produce laudanosoline and its analogs. The compound's unique structure and biological activity make it an attractive target for drug discovery and development.'

ID Source	ID
PubMed CID	92716
CHEMBL ID	19844
CHEBI ID	31764
SCHEMBL ID	13356020
MeSH ID	M0255088

Synonym
dl-6,7-dimethoxy-1-((3,4-dimethoxyphenyl)methyl)-2-methylisoquinoline hydrobromide trihydrate
einecs 207-613-4
OPREA1_429345
laudanosoline
485-33-6
(r,s)-laudanosoline
NCGC00163586-01
bdbm50291683
chebi:31764 ,
CHEMBL19844 ,
1-(3,4-dihydroxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
1-[(3,4-dihydroxyphenyl)methyl]-2-methyl-3,4-dihydro-1h-isoquinoline-6,7-diol
d,l-laudanosoline (jw9-3)
1-(3,4-dihydroxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol
einecs 260-635-6
(s)-1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol
nsc 99800
einecs 281-783-8
(1)-1-((3,4-dihydroxyphenyl)methyl)-1,2,3,4-tetrahydro-2-methylisoquinoline-6,7-diol hydrobromide
ST50307991 ,
FT-0632201
SCHEMBL13356020
AKOS024306970
6,7-isoquinolinediol, 1-[(3,4-dihydroxyphenyl)methyl]-1,2,3,4-tetrahydro-2-methyl-
1-(3,4-dihydroxybenzyl)-2-methyl-1,2,3,4-tetrahydro-6,7-isoquinolinediol #
VHRSWCTVFBWHKE-UHFFFAOYSA-N
sr-05000002260
SR-05000002260-2
dl-laudanosoline hydrobromide trihydrate
Q27114681
DTXSID60964073
1-[(3,4-dihydroxyphenyl)methyl]-2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Class	Description
isoquinolines	A class of organic heteropolycyclic compound consisting of isoquinoline and its substitution derivatives.
[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 (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
phosphopantetheinyl transferase	Bacillus subtilis	Potency	56.2341	0.1413	37.9142	100.0000	AID1490
DNA polymerase kappa isoform 1	Homo sapiens (human)	Potency	33.5875	0.0316	22.3146	100.0000	AID588579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Polymerase acidic protein	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50 (µMol)	1.8800	1.8800	4.6880	5.8600	AID1888156
Polymerase acidic protein	Influenza A virus (A/duck/Hokkaido/8/1980(H3N8))	IC50 (µMol)	2.0000	2.0000	2.0000	2.0000	AID1800133
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
extracellular region	Polymerase acidic protein	Influenza A virus (A/Puerto Rico/8/1934(H1N1))
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay ID	Title	Year	Journal	Article
AID1888156	Inhibition of Influenza A virus N-terminal domain of PA endonuclease using 6FAM-TGGCAATATCAGCTCCACA-MGBNFQ as fluorescent substrate by FRET analysis	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and optimization of new 6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as potent influenza virus PA
AID1888148	Antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in MDCK cells assessed as reduction in virus induced cytopathic effect measured 48 hrs post infection by MTT assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and optimization of new 6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as potent influenza virus PA
AID1888149	Cytotoxicity against MDCK cells assessed as reduction in cell viability incubated for 48 hrs by MTT assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and optimization of new 6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as potent influenza virus PA
AID1888150	Selectivity index, ratio of CC50 for cytotoxicity against MDCK cells to EC50 for antiviral activity against Influenza A virus A/WSN/33(H1N1) infected in MDCK cells	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and optimization of new 6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as potent influenza virus PA
AID1800133	Fragment Screening from Article 10.1021/cb400400j: \\Crystallographic fragment screening and structure-based optimization yields a new class of influenza endonuclease inhibitors.\\	2013	ACS chemical biology, Nov-15, Volume: 8, Issue:11	Crystallographic fragment screening and structure-based optimization yields a new class of influenza endonuclease inhibitors.
[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	3 (50.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	1 (16.67)	24.3611
2020's	2 (33.33)	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	6 (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
pindolol Pindolol: A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638). pindolol : A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.	1.99	1	indoles; secondary amine	antiglaucoma drug; antihypertensive agent; beta-adrenergic antagonist; serotonergic antagonist; vasodilator agent
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3.	1.99	1	naphthalenes; propanolamine; secondary amine	anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic
apomorphine Apomorphine: A derivative of morphine that is a dopamine D2 agonist. It is a powerful emetic and has been used for that effect in acute poisoning. It has also been used in the diagnosis and treatment of parkinsonism, but its adverse effects limit its use.	1.98	1	aporphine alkaloid	alpha-adrenergic drug; antidyskinesia agent; antiparkinson drug; dopamine agonist; emetic; serotonergic drug
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3.	1.99	1	erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan	antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite
laudanosine laudanosine: opium alkaloid	2.39	2	isoquinolines
tetrahydropapaveroline Tetrahydropapaveroline: A leukomaine (animal alkaloid) formed in brain and liver from dopamine and L-dopa; it may be implicated in psychiatric problems.	2.39	2	benzylisoquinoline alkaloid; benzyltetrahydroisoquinoline; isoquinolinol	human metabolite
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.41	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
metaperiodate Periodic Acid: A strong oxidizing agent.	1.98	1	iodine oxoacid
salsolinol salsolinol: RN given refers to cpd without isomeric designation; EP to SALSOLINE ALKALOIDS (78-82); on-line search SALSOLINE ALKALOIDS (78-82); Index Medicus search ISOQUINOLINES (78-82). (S)-salsolinol : A 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol that has S-configuration.	1.98	1	1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol	human urinary metabolite
cinchonidine cinchonidine: has antimalarial activity; diastereoisomer of cinchonine with distinct physiochemical properties; RN given refers to parent cpd(8alpha,9R)-isomer. cinchonidine : 8-epi-Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (R configuration). A diasteroisomer of cinchonine, it occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	1.99	1	(8xi)-cinchonan-9-ol; cinchona alkaloid	metabolite
bcx 1812 [no description available]	2.41	1	3-hydroxy monocarboxylic acid; acetamides; cyclopentanols; guanidines	antiviral drug; EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
metaperiodate metaperiodate: RN given refers to periodic acid, Na salt; structure. periodate : A monovalent inorganic anion obtained by deprotonation of periodic acid.	1.98	1	iodine oxoanion; monovalent inorganic anion
epicinchonine epicinchonine: structure in first source. cinchonine : Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis.	1.99	1	cinchona alkaloid
tryptophanol tryptophanol: RN given refers to cpd without isomeric designation	1.99	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	1.99	1	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Grippe [description not available]	3.52	4
Influenza, Human An acute viral infection in humans involving the respiratory tract. It is marked by inflammation of the NASAL MUCOSA; the PHARYNX; and conjunctiva, and by headache and severe, often generalized, myalgia.	3.52	4
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	1.99	1

laudanosoline

Cross-References

Synonyms (32)

Drug Classes (1)

Protein Targets (4)

Potency Measurements

Inhibition Measurements

Ceullar Components (1)

Bioassays (5)

Research

Studies (6)

Study Types

laudanosoline

Cross-References

Synonyms (32)

Drug Classes (1)

Protein Targets (4)

Potency Measurements

Inhibition Measurements

Ceullar Components (1)

Bioassays (5)

Research

Studies (6)

Study Types

Related Drugs (15)

Related Conditions (3)