Page last updated: 2024-12-07

tetrahydroharmane

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

Tetrahydroharmane (THH) is a beta-carboline alkaloid found in various plants and animals. It is synthesized through the condensation of tryptamine and a suitable carbonyl compound. THH exhibits a wide range of pharmacological effects, including antidepressant, anxiolytic, and neuroprotective properties. Research interest in THH stems from its potential therapeutic applications in treating neurodegenerative diseases, depression, and anxiety. Studies have investigated its mechanisms of action, which involve interactions with various neurotransmitter systems, including serotonin, dopamine, and GABA. THH has also been linked to the modulation of brain plasticity and neurotrophic factor expression. However, further research is needed to elucidate the full therapeutic potential and safety profile of this compound.'

Cross-References

ID SourceID
PubMed CID91522
CHEMBL ID440524
SCHEMBL ID7018798
MeSH IDM0080667

Synonyms (61)

Synonym
NCIOPEN2_001385
2506-10-7
nsc92525
1,3,4-tetrahydroharmane
nsc-92525
1,3,4-tetrahydroharman
methtryptoline
harman,2,3,4-tetrahydro-
OPREA1_069935
OPREA1_717157
EU-0013732
525-40-6
tetrahydroharman
1-methyl-2,3,4,9-tetrahydro-1h-beta-carboline
bdbm50132092
CHEMBL440524 ,
AKOS000274320
FT-0691125
AKOS016300451
1-methyl-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole
1h-pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-1-methyl-, (+-)-
STK724371
dl-eleagnin
1-methyl-2,3,4,9-tetrahydro-1h-ss-carboline
1,2,3,4-tetrahydroharmane
w6clk26x7v ,
nsc 92525
einecs 219-711-4
1,2,3,4-tetrahydroharman
tetrahydroharmane
1h-pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-1-methyl-
harman, 1,2,3,4-tetrahydro-
unii-w6clk26x7v
2,3,4,9-tetrahydro-1-methyl-1h-pyrido(3,4-b)indole
MS-3709
1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indole
SCHEMBL7018798
.beta.-carboline, 1-methyltetrahydro
1-methyl-1,2,3,4-tetrahydro-.beta.-carboline
1-methyl-2,3,4,9-tetrahydro-1h-beta-carboline #
1-methyltetrahydro-.beta.-carboline
1h-pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-1-methyl-
LPIJOZBIVDCQTE-UHFFFAOYSA-N
(.+/-.)-tetrahydroharmane
eleagnine
mfcd00046879
sr-01000505230
Z204323524
SR-01000505230-1
F1983-0033
Q7706553
1-methyl-2,3,4,9-tetrahydro-1h-b-carboline
(+/-)-tetrahydroharman
(+/-)-tetrahydroharmane
1-methyl-2,3,4,9-tetrahydro-1h-pyrido(3,4-b)indole
(+/-)-1-methyl-1,2,3,4-tetrahydro-.beta.-carboline
9-azabicyclo[3.3.1]nonan-3-amine, 9-methyl-, hydrochloride (1:2)
SB45840
EN300-42800
DTXSID901027440
CS-0249214

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
", fast and slow metabolizers of harmine-in 14 experienced male members of the União do Vegetal (UDV) who received a standardized dosage of hoasca."( Fast and slow metabolizers of Hoasca.
Callaway, JC, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 5AHomo sapiens (human)Ki10.00000.00080.94335.1600AID6500
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
hippocampus development5-hydroxytryptamine receptor 5AHomo sapiens (human)
response to estradiol5-hydroxytryptamine receptor 5AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 5AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 5AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 5AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 5AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 5AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 5AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
perikaryon5-hydroxytryptamine receptor 5AHomo sapiens (human)
postsynaptic specialization membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 5AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 5AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID453270Cytotoxicity in human THP1 cells2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID6500Binding affinity towards 5-hydroxytryptamine 5A receptor using lysergic acid diethylamide (LSD) as radioligand2003Journal of medicinal chemistry, Aug-28, Volume: 46, Issue:18
Binding of tetrahydrocarboline derivatives at human 5-HT5A receptors.
AID453269Antimalarial activity against chloroquine-resistant Plasmodium falciparum W22009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID453268Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D62009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Structure-activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues.
AID1846870Antimalarial activity against multi drug resistant Plasmodium falciparum W22021European journal of medicinal chemistry, Oct-05, Volume: 221Structure activity relationship in β-carboline derived anti-malarial agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (50.00)18.7374
1990's1 (7.14)18.2507
2000's5 (35.71)29.6817
2010's0 (0.00)24.3611
2020's1 (7.14)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.58

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 Index11.58 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.41 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (6.67%)5.53%
Reviews2 (13.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]