Compounds > 10,11-dihydroxy-n-allylnoraporphine
Page last updated: 2024-12-09

10,11-dihydroxy-n-allylnoraporphine

Description

10,11-dihydroxy-N-allylnoraporphine, often abbreviated as **DHAN**, is a synthetic derivative of the alkaloid aporphine. It's important for research because of its potential therapeutic applications in treating neurological disorders.

Here's a breakdown of its importance:

**What it is:**

* **Aporphine derivative:** DHAN is structurally similar to naturally occurring aporphine alkaloids, which are found in various plants.
* **Synthetic:** DHAN is not found naturally and must be synthesized in a lab.
* **N-allyl group:** This structural modification differentiates DHAN from other aporphine derivatives.

**Why it's important for research:**

* **Neuroprotective effects:** Studies have shown that DHAN exhibits neuroprotective properties, potentially protecting neurons from damage caused by oxidative stress, inflammation, and other factors that contribute to neurodegenerative diseases.
* **Antioxidant activity:** DHAN possesses strong antioxidant activity, which may be beneficial in combating oxidative stress, a major contributing factor to aging and disease.
* **Possible therapeutic potential for neurological disorders:** Due to its neuroprotective and antioxidant properties, DHAN is being investigated as a potential treatment for various neurological conditions, including Alzheimer's disease, Parkinson's disease, and stroke.
* **Potential for drug development:** The research on DHAN could lead to the development of new and effective therapies for neurological disorders.

**Current research focus:**

* Understanding the exact mechanisms of DHAN's neuroprotective and antioxidant effects.
* Investigating its efficacy and safety in preclinical models of neurological disorders.
* Developing novel drug delivery systems for DHAN to enhance its bioavailability and therapeutic efficacy.

While research on DHAN is promising, it's still in its early stages. More research is needed to fully understand its potential and ensure its safety and efficacy in humans.

10,11-dihydroxy-N-allylnoraporphine: RN refers to (R)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID838674
CHEMBL ID318111
CHEBI ID92130
SCHEMBL ID12305058
MeSH IDM0183890

Synonyms (25)

Synonym
CHEMBL318111 ,
4h-dibenzo(de,g)quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-(2-propenyl)-, (r)-
18426-17-0
10,11-dihydroxy-n-allylnoraporphine
BRD-K07079548-001-01-9
(r)-6-allyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
BPBIO1_001351
BIOMOL-NT_000063
LOPAC0_000406
NCGC00162144-03
(r)6-allyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
6-allyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol; hydrobromide
bdbm50007423
cid_11957524
CCG-204499
SCHEMBL12305058
CHEBI:92130
(8r)-7-prop-2-enyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-13,14-diol
Q27163914
6-(prop-2-en-1-yl)-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
DTXSID90939810
SDCCGSBI-0050392.P002
(6ar)-6-prop-2-enyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
r(-)-n-allylnorapomorphine
AKOS040757092
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aporphine alkaloidAny benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative.
[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 (22)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
dopamine D1 receptorHomo sapiens (human)Potency0.05170.00521.30228.1995AID624455
thioredoxin reductaseRattus norvegicus (Norway rat)Potency4.27430.100020.879379.4328AID488773; AID588453; AID588456
ATAD5 protein, partialHomo sapiens (human)Potency32.62940.004110.890331.5287AID493107
GLS proteinHomo sapiens (human)Potency0.89130.35487.935539.8107AID624146
hypothetical protein, conservedTrypanosoma bruceiPotency13.45910.223911.245135.4813AID624147
regulator of G-protein signaling 4Homo sapiens (human)Potency33.58750.531815.435837.6858AID504845
ParkinHomo sapiens (human)Potency32.64270.819914.830644.6684AID720573
arylsulfatase AHomo sapiens (human)Potency37.93301.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency0.53230.035520.977089.1251AID504332
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency58.47890.016525.307841.3999AID602332
NPC intracellular cholesterol transporter 1 precursorHomo sapiens (human)Potency58.04790.01262.451825.0177AID485313
D(1A) dopamine receptorHomo sapiens (human)Potency0.46610.02245.944922.3872AID488981; AID488982; AID488983
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency10.00000.354828.065989.1251AID504847
chromobox protein homolog 1Homo sapiens (human)Potency44.66840.006026.168889.1251AID488953
ras-related protein Rab-9AHomo sapiens (human)Potency58.04790.00022.621531.4954AID485297
serine/threonine-protein kinase mTOR isoform 1Homo sapiens (human)Potency16.74180.00378.618923.2809AID2667; AID2668
M-phase phosphoprotein 8Homo sapiens (human)Potency23.77810.177824.735279.4328AID488949
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency39.81070.251215.843239.8107AID504327
D(1A) dopamine receptorSus scrofa (pig)Potency7.36210.00378.108123.2809AID2667
Ataxin-2Homo sapiens (human)Potency35.48130.011912.222168.7989AID588378
2,3-bisphosphoglycerate-independent phosphoglycerate mutaseLeishmania major strain FriedlinPotency37.93307.568615.230621.3313AID504548
ATP-dependent phosphofructokinaseTrypanosoma brucei brucei TREU927Potency4.77550.060110.745337.9330AID485368
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
negative regulation of receptor internalizationAtaxin-2Homo sapiens (human)
regulation of translationAtaxin-2Homo sapiens (human)
RNA metabolic processAtaxin-2Homo sapiens (human)
P-body assemblyAtaxin-2Homo sapiens (human)
stress granule assemblyAtaxin-2Homo sapiens (human)
RNA transportAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
RNA bindingAtaxin-2Homo sapiens (human)
epidermal growth factor receptor bindingAtaxin-2Homo sapiens (human)
protein bindingAtaxin-2Homo sapiens (human)
mRNA bindingAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
cytoplasmAtaxin-2Homo sapiens (human)
Golgi apparatusAtaxin-2Homo sapiens (human)
trans-Golgi networkAtaxin-2Homo sapiens (human)
cytosolAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
membraneAtaxin-2Homo sapiens (human)
perinuclear region of cytoplasmAtaxin-2Homo sapiens (human)
ribonucleoprotein complexAtaxin-2Homo sapiens (human)
cytoplasmic stress granuleAtaxin-2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID65276Compound was evaluated for its ability to inhibit Dopamine receptor D2 in rat striatum using [3H]spiperone1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.
AID63013Compound was evaluated for its ability to inhibit Striatal Dopamine receptor in rat brain through radioreceptor assay carried out with agonist ligand.1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.
AID61505Compound was evaluated for its ability to inhibit Dopamine receptor D1 in rat striatum using [3H]SCH-233901991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.
AID226743Potency ratio calculated from the ratio of D2 to that of D1 receptors1991Journal of medicinal chemistry, Jan, Volume: 34, Issue:1
R and S enantiomers of 11-hydroxy- and 10,11-dihydroxy-N-allylnoraporphine: synthesis and affinity for dopamine receptors in rat brain tissue.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (12.50)18.2507
2000's1 (12.50)29.6817
2010's3 (37.50)24.3611
2020's3 (37.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.65

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 Index12.65 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
n-n-propylnorapomorphine
[no description available]		1.9710aporphine alkaloid
11-hydroxy-n-(n-propyl)noraporphine hydrochloride, (r)-isomer
[no description available]		1.9710
ConditionIndicatedRelationship StrengthStudiesTrials
Anemia, Fanconi
[description not available]		02.1310
Fanconi Anemia
Congenital disorder affecting all bone marrow elements, resulting in ANEMIA; LEUKOPENIA; and THROMBOPENIA, and associated with cardiac, renal, and limb malformations as well as dermal pigmentary changes. Spontaneous CHROMOSOME BREAKAGE is a feature of this disease along with predisposition to LEUKEMIA. There are at least 7 complementation groups in Fanconi anemia: FANCA, FANCB, FANCC, FANCD1, FANCD2, FANCE, FANCF, FANCG, and FANCL. (from Online Mendelian Inheritance in Man, http://www.ncbi.nlm.nih.gov/entrez/dispomim.cgi?id=227650, August 20, 2004)		02.1310
Contact Dermatitis
[description not available]		02.2110
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2110
Itching
[description not available]		02.2110
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		02.2110
Pruritus
An intense itching sensation that produces the urge to rub or scratch the skin to obtain relief.		02.2110
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