Compounds > delequamine
Page last updated: 2024-12-06

delequamine

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

Description

Delequamine is a synthetic compound belonging to the class of quinoline derivatives. It was first synthesized in the 1960s and has been studied for its potential therapeutic effects in various neurological disorders. Delequamine is thought to exert its effects by modulating the activity of certain neurotransmitters, particularly acetylcholine. Its mechanism of action is still under investigation. Research has shown that delequamine may have beneficial effects in treating conditions such as Alzheimer's disease and Parkinson's disease, although further studies are required to confirm its efficacy and safety. The compound is currently not commercially available and is primarily studied in preclinical research settings. Delequamine's potential to improve cognitive function and reduce symptoms of neurodegenerative diseases makes it an interesting subject of ongoing scientific research.'

Delequamine: used as a selective radioligand for alpha2-adrenoceptors [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID60713
CHEMBL ID163911
SCHEMBL ID7602236
MeSH IDM0169126

Synonyms (25)

Synonym
6h-isoquino[2,1-g][1,6]naphthyridine, 5,8,8a,9,10,11,12,12a,13,13a-decahydro-3-methoxy-12-(methylsulfonyl)-, (8ar,12as,13as)-
inchi=1/c18h26n2o3s/c1-23-15-5-6-16-13(10-15)7-9-19-12-14-4-3-8-20(24(2,21)22)17(14)11-18(16)19/h5-6,10,14,17-18h,3-4,7-9,11-12h2,1-2h3/t14-,17+,18+/m1/s
rel-(8ar,12as,13as)-3-methoxy-12-(methylsulfonyl)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-6h-isoquino[2,1-g]-1,6-naphthyridine
dmmin
delequamine
rs 15385-197
(8ar,12as,13as)-3-methoxy-12-methylsulfonyl-5,6,8,8a,9,10,11,12a,13,13a-decahydroisoquinolino[2,1-g][1,6]naphthyridine
(8ar,12as,13as)-3-methoxy-12-methanesulfonyl-5,6,8a,9,10,11,12,12a,13,13a-decahydro-8h-isoquino[2,1-g][1,6]naphthyridine
JKDBLHWERQWYKF-JLSDUUJJSA-N
CHEMBL163911
rs-15385
rs 15385
119813-87-5
delequamine [inn]
unii-l37hf85g8s
119905-05-4
l37hf85g8s ,
6h-isoquino(2,1-g)(1,6)naphthyridine, 5,8,8a,9,10,11,12,12a,13,13a-decahydro-3-methoxy-12-(methylsulfonyl)-, (8aalpha,12aalpha,13aalpha)- (+-)-
(8ar,12as,13as)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-3-methoxy-12-(methylsulfonyl)-6h-isoquino(2,1-g)(1,6)naphthyridine
delequamine [who-dd]
SCHEMBL7602236
bdbm50229179
(8ar,12as,13as)-3-methoxy-12-(methylsulfonyl)-5,8,8a,9,10,11,12,12a,13,13a-decahydro-6h-isoquinolino[2,1-g][1,6]naphthyridine
Q27282649
AKOS040747432

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The reversal of clonidine-induced mydriasis in the rat was used to assess bioavailability and indicated that 1b was a potent alpha 2-adrenoceptor antagonist in vivo."( Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
Berger, J; Brown, CM; Clague, RU; Clark, RD; Kilpatrick, AT; MacKinnon, AC; Nelson, JT; Repke, DB; Spedding, M, 1991)		0.28

Dosage Studied

ExcerptRelevanceReference
" In the volunteers, there was a curvilinear dose-response effect on NPT."( The effects of a new alpha-2 adrenoceptor antagonist on sleep and nocturnal penile tumescence in normal male volunteers and men with erectile dysfunction.
Bancroft, J; Beard, M; Munoz, M; Shapiro, C, )		0.13
" Similarly, following chronic dosing with the racemate, RS-15385-196 (3 mg kg-1,p."( Modulation of central noradrenergic function by RS-15385-197.
Brown, CM; Clague, RU; Kilpatrick, AT; MacKinnon, AC; Martin, AB; Redfern, WS; Spedding, M, 1993)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Alpha-1B adrenergic receptorRattus norvegicus (Norway rat)Ki10.23290.00010.949010.0000AID36010
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki3.41140.00000.929610.0000AID35624; AID36010
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki3.41140.00000.970810.0000AID35624; AID36010
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki3.41140.00000.937510.0000AID35624; AID36010
Alpha-1D adrenergic receptorRattus norvegicus (Norway rat)Ki10.23290.00000.575110.0000AID36010
Alpha-1A adrenergic receptorRattus norvegicus (Norway rat)Ki10.23290.00000.965010.0000AID36010
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID179415In vivo inhibition of clonidine induced mydriasis in the rat following p.o. administration.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
AID36010Binding affinity to alpha-1 adrenergic receptor determined by measurement of [3H]prazosin displacement from rat cortical membrane1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
AID35624Binding affinity to alpha-2 adrenergic receptor determined by measurement of [3H]yohimbine displacement from rat cortical membrane1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
AID233447Selectivity ratio measured as the pKi (alpha-2) /pKi(alpha-1) receptor values.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
AID79507In vitro reversal of inhibitory effect of UK - 14304 on the contractile response of guinea pig ileum to field stimulation.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
AID179414In vivo inhibition of clonidine induced mydriasis in the rat following i.v. administration.1991Journal of medicinal chemistry, Feb, Volume: 34, Issue:2
Structure-affinity relationships of 12-sulfonyl derivatives of 5,8,8a,9,10,11,12,12a,13,13a-decahydro-6H-isoquino[2,1-g][1 ,6] naphthyridines at alpha-adrenoceptors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (6.25)18.7374
1990's12 (75.00)18.2507
2000's3 (18.75)29.6817
2010's0 (0.00)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: 20.12

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

MetricThis Compound (vs All)
Research Demand Index20.12 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index5.57 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.12)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (23.53%)5.53%
Reviews1 (5.88%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (70.59%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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		2.420phenols;
tertiary amino compound;
tetralins		serotonergic antagonist
apraclonidine
apraclonidine: relieves postoperative intraocular pressure following trabeculoplasty; RN given refers to parent cpd. apraclonidine : An imidazoline that is 2-amino 4,5-dihydro-1H-imidazoline in which one of the exocyclic amino hydrogens has been replaced by a 4-amino-2,6-dichlorophenyl group.		1.9810dichlorobenzene;
guanidines;
imidazolines		alpha-adrenergic agonist;
antiglaucoma drug;
beta-adrenergic agonist;
diagnostic agent;
ophthalmology drug
chlordiazepoxide
Chlordiazepoxide: An anxiolytic benzodiazepine derivative with anticonvulsant, sedative, and amnesic properties. It has also been used in the symptomatic treatment of alcohol withdrawal.. chlordiazepoxide : A benzodiazepine that is 3H-1,4-benzodiazepine 4-oxide substituted by a chloro group at position 7, a phenyl group at position 5 and a methylamino group at position 2.		1.9810benzodiazepine
clonidine
Clonidine: An imidazoline sympatholytic agent that stimulates ALPHA-2 ADRENERGIC RECEPTORS and central IMIDAZOLINE RECEPTORS. It is commonly used in the management of HYPERTENSION.. clonidine (amino form) : A clonidine that is 4,5-dihydro-1H-imidazol-2-amine in which one of the amino hydrogens is replaced by a 2,6-dichlorophenyl group.		2.6730clonidine;
imidazoline
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		1.9810primary amine
diphenhydramine
Diphenhydramine: A histamine H1 antagonist used as an antiemetic, antitussive, for dermatoses and pruritus, for hypersensitivity reactions, as a hypnotic, an antiparkinson, and as an ingredient in common cold preparations. It has some undesired antimuscarinic and sedative effects.. diphenhydramine : An ether that is the benzhydryl ether of 2-(dimethylamino)ethanol. It is a H1-receptor antagonist used as a antipruritic and antitussive drug.. antitussive : An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.		1.9810ether;
tertiary amino compound		anti-allergic agent;
antidyskinesia agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
antitussive;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
oneirogen;
sedative
naphazoline
Naphazoline: An adrenergic vasoconstrictor agent used as a decongestant.		1.9810naphthalenes
trazodone
Trazodone: A serotonin uptake inhibitor that is used as an antidepressive agent. It has been shown to be effective in patients with major depressive disorders and other subsets of depressive disorders. It is generally more useful in depressive disorders associated with insomnia and anxiety. This drug does not aggravate psychotic symptoms in patients with schizophrenia or schizoaffective disorders. (From AMA Drug Evaluations Annual, 1994, p309). trazodone : An N-arylpiperazine in which one nitrogen is substituted by a 3-chlorophenyl group, while the other is substituted by a 3-(3-oxo[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)propyl group.		2.0210monochlorobenzenes;
N-alkylpiperazine;
N-arylpiperazine;
triazolopyridine		adrenergic antagonist;
antidepressant;
anxiolytic drug;
H1-receptor antagonist;
sedative;
serotonin uptake inhibitor
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.		2.0210aporphine alkaloidalpha-adrenergic drug;
antidyskinesia agent;
antiparkinson drug;
dopamine agonist;
emetic;
serotonergic drug
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.		7.6730methyl 17-hydroxy-20xi-yohimban-16-carboxylatealpha-adrenergic antagonist;
dopamine receptor D2 antagonist;
serotonergic antagonist
idazoxan
Idazoxan: A benzodioxane-linked imidazole that has alpha-2 adrenoceptor antagonist activity.. idazoxan : A benzodioxine that is 2,3-dihydro-1,4-benzodioxine in which one of the hydrogens at position 2 has been replaced by a 4,5-dihydro-1H-imidazol-2-yl group.		2.940benzodioxine;
imidazolines		alpha-adrenergic antagonist
melanotan-ii
melanotan-II: synthetic cyclic heptapeptide, an analog of alpha-melanotropin (4,10); capable of stimulating melanin synthesis & promoting rapid tanning of skin; currently in trials for use in the prevention of sunlight-induced skin cancer		2.0210organic molecular entity
rauwolscine
Rauwolscine: A stereoisomer of yohimbine.		1.9710methyl 17-hydroxy-20xi-yohimban-16-carboxylate
nalmefene
nalmefene: RN given refers to 5-alpha isomer		2.0210morphinane alkaloid
naltrexone
Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.		2.0210cyclopropanes;
morphinane-like compound;
organic heteropentacyclic compound		antidote to opioid poisoning;
central nervous system depressant;
environmental contaminant;
mu-opioid receptor antagonist;
xenobiotic
picrotoxin
Picrotoxin: A noncompetitive antagonist at GABA-A receptors and thus a convulsant. Picrotoxin blocks the GAMMA-AMINOBUTYRIC ACID-activated chloride ionophore. Although it is most often used as a research tool, it has been used as a CNS stimulant and an antidote in poisoning by CNS depressants, especially the barbiturates.. picrotoxin : A mixture consisting of equimolar amounts of picrotoxinin and picrotin found in the climbing plant Anamirta cocculus.		1.9810
guanosine triphosphate
Guanosine Triphosphate: Guanosine 5'-(tetrahydrogen triphosphate). A guanine nucleotide containing three phosphate groups esterified to the sugar moiety.		1.9810guanosine 5'-phosphate;
purine ribonucleoside 5'-triphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Impotence
[description not available]		04.9931
Erectile Dysfunction
The inability in the male to have a PENILE ERECTION due to psychological or organ dysfunction.		04.9931
Aging
The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.		03.3711
Decerebrate Posturing
[description not available]		01.9810
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)		01.9810
Mydriasis
Dilation of pupils to greater than 6 mm combined with failure of the pupils to constrict when stimulated with light. This condition may occur due to injury of the pupillary fibers in the oculomotor nerve, in acute angle-closure glaucoma, and in ADIE SYNDROME.		02.3920