Page last updated: 2024-12-08

18-Hydroxy-11,17-dimethoxyyohimban-16-carboxylic acid

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

18-Hydroxy-11,17-dimethoxyyohimban-16-carboxylic acid, often referred to as **18-Hydroxy-yohimbine**, is a naturally occurring indole alkaloid found in plants of the *Yohimbe* genus. It's a structural analog of yohimbine, a well-known compound with a range of pharmacological activities, including:

* **Alpha-2 adrenergic receptor antagonist:** Yohimbine and its analogs block the action of norepinephrine and epinephrine at these receptors, potentially leading to increased arousal, blood pressure, and heart rate.
* **Antidepressant properties:** Some research suggests yohimbine can improve symptoms of depression, possibly by affecting serotonin and dopamine levels.
* **Potential for erectile dysfunction treatment:** Yohimbine is marketed as an aphrodisiac and potential treatment for erectile dysfunction, although its effectiveness is debatable.
* **Other effects:** Yohimbine has also been investigated for its potential use in treating fatigue, anxiety, and other conditions.

**Importance for Research:**

18-Hydroxy-yohimbine is of research interest for several reasons:

* **Structure-activity relationship studies:** Understanding the differences in pharmacological effects between 18-Hydroxy-yohimbine and yohimbine can help researchers understand how specific structural modifications influence the activity of these compounds. This can lead to the development of more potent and selective drugs with fewer side effects.
* **New drug discovery:** 18-Hydroxy-yohimbine itself may have therapeutic potential, offering unique benefits compared to yohimbine. Research exploring its specific effects and applications is ongoing.
* **Understanding the role of natural products in health:** Investigating the pharmacological activities of naturally occurring compounds like 18-Hydroxy-yohimbine can contribute to the development of novel therapeutic agents and better understanding of traditional medicinal practices.

**However, it's crucial to note that:**

* 18-Hydroxy-yohimbine is a relatively understudied compound, and much research is still needed to understand its full potential and safety profile.
* The use of yohimbine and its analogs should be carefully considered due to potential side effects, such as anxiety, restlessness, increased heart rate, and gastrointestinal distress.
* It's essential to consult with a healthcare professional before using any supplements or medications containing these compounds.

In summary, 18-Hydroxy-yohimbine is a fascinating compound with potential for research and drug development. However, further investigation is needed to fully understand its pharmacological properties and safety profile.

Cross-References

ID SourceID
PubMed CID419781
CHEMBL ID1570525
CHEBI ID181717
SCHEMBL ID14286189

Synonyms (12)

Synonym
17-hydroxy-6,18-dimethoxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
CHEBI:181717
18-hydroxy-11,17-dimethoxyyohimban-16-carboxylic acid
mls000737091 ,
smr000528366
HMS2268I03
CHEMBL1570525
bdbm52830
cid_419781
6,18-dimethoxy-17-oxidanyl-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid
SCHEMBL14286189
DTXSID70871562
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
acid sphingomyelinaseHomo sapiens (human)Potency19.952614.125424.061339.8107AID504937
USP1 protein, partialHomo sapiens (human)Potency31.62280.031637.5844354.8130AID743255
Microtubule-associated protein tauHomo sapiens (human)Potency31.62280.180013.557439.8107AID1460
Bloom syndrome protein isoform 1Homo sapiens (human)Potency39.81070.540617.639296.1227AID2528
chromobox protein homolog 1Homo sapiens (human)Potency2.23870.006026.168889.1251AID540317
importin subunit beta-1 isoform 1Homo sapiens (human)Potency64.46795.804836.130665.1308AID540253; AID540263
snurportin-1Homo sapiens (human)Potency64.46795.804836.130665.1308AID540253; AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency50.11870.425612.059128.1838AID504891
GTP-binding nuclear protein Ran isoform 1Homo sapiens (human)Potency39.81075.804816.996225.9290AID540253
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency100.00000.050127.073689.1251AID588590
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
POsterior SegregationCaenorhabditis elegansEC50 (µMol)300.00002.201047.1808186.6810AID1964
Sodium-dependent noradrenaline transporter Homo sapiens (human)EC50 (µMol)300.00000.082031.0243168.9080AID1960
Zinc finger protein mex-5Caenorhabditis elegansEC50 (µMol)300.00000.082033.5679168.9080AID1960
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (11)

Processvia Protein(s)Taxonomy
monoamine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transportSodium-dependent noradrenaline transporter Homo sapiens (human)
chemical synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
response to xenobiotic stimulusSodium-dependent noradrenaline transporter Homo sapiens (human)
response to painSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine uptakeSodium-dependent noradrenaline transporter Homo sapiens (human)
neuron cellular homeostasisSodium-dependent noradrenaline transporter Homo sapiens (human)
amino acid transportSodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine transportSodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine uptake involved in synaptic transmissionSodium-dependent noradrenaline transporter Homo sapiens (human)
sodium ion transmembrane transportSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
actin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
neurotransmitter:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
dopamine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
norepinephrine:sodium symporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
protein bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
monoamine transmembrane transporter activitySodium-dependent noradrenaline transporter Homo sapiens (human)
alpha-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
metal ion bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
beta-tubulin bindingSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
cell surfaceSodium-dependent noradrenaline transporter Homo sapiens (human)
membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
neuronal cell body membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
presynaptic membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
plasma membraneSodium-dependent noradrenaline transporter Homo sapiens (human)
axonSodium-dependent noradrenaline transporter Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (20.00)29.6817
2010's3 (60.00)24.3611
2020's1 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.56

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 Index12.56 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.56)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]