Compounds > tetrahydroharmine
Page last updated: 2024-12-08

tetrahydroharmine

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

Cross-References

ID SourceID
PubMed CID159809
CHEMBL ID129208
SCHEMBL ID646273
MeSH IDM0108797

Synonyms (38)

Synonym
MLS001049053
smr000386892
nsc-99788
leptaflorine
nsc99788
486-93-1
17019-01-1
tetrahydroharmine
NCIOPEN2_006596
7-methoxy-1-methyl-2,3,4,9-tetrahydro-1h-beta-carboline
cid_159809
bdbm50132130
CHEMBL129208 ,
7-methoxy-1-methyl-2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole
AKOS004119339
NCGC00246230-01
1h-pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-7-methoxy-1-methyl- (van)
1,2,3,4-tetrahydroharmine
unii-f1q1e0g45a
f1q1e0g45a ,
HMS2271A13
AKOS016339742
SCHEMBL646273
AB00637144-07
7-methoxy-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indole
RS-0341
harmine, 1,2,3,4-tetrahydro-
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N
7-methoxy-1-methyl-2,3,4,9-tetrahydro-1h-beta-carboline #
1h-pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-7-methoxy-1-methyl-
tetrahydroharmine, (+/-)-
2,3,4,9-tetrahydro-7-methoxy-1-methyl-1h-pyrido(3,4-b)indole
mfcd05672237
(+/-)-tetrahydroharmine
Q135068
7-methoxy-1-methyl-2,4a,4b,8a,9,9a-hexahydro-1h-pyrido[3,4-b]indole
A901773
DTXSID70901873
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (24)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, JmjC domain-containing histone demethylation protein 3AHomo sapiens (human)Potency50.11870.631035.7641100.0000AID504339
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency25.11890.177814.390939.8107AID2147
acid sphingomyelinaseHomo sapiens (human)Potency39.810714.125424.061339.8107AID504937
thioredoxin reductaseRattus norvegicus (Norway rat)Potency53.88200.100020.879379.4328AID588453; AID588456
USP1 protein, partialHomo sapiens (human)Potency8.91250.031637.5844354.8130AID743255
GLS proteinHomo sapiens (human)Potency7.94330.35487.935539.8107AID624170
TDP1 proteinHomo sapiens (human)Potency6.45770.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency1.12200.180013.557439.8107AID1460
thioredoxin glutathione reductaseSchistosoma mansoniPotency11.22020.100022.9075100.0000AID485364
bromodomain adjacent to zinc finger domain 2BHomo sapiens (human)Potency50.11870.707936.904389.1251AID504333
lysosomal alpha-glucosidase preproproteinHomo sapiens (human)Potency39.81070.036619.637650.1187AID2100
importin subunit beta-1 isoform 1Homo sapiens (human)Potency56.23415.804836.130665.1308AID540263
DNA polymerase betaHomo sapiens (human)Potency28.18380.022421.010289.1251AID485314
flap endonuclease 1Homo sapiens (human)Potency39.81070.133725.412989.1251AID588795
snurportin-1Homo sapiens (human)Potency56.23415.804836.130665.1308AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency31.62280.425612.059128.1838AID504891
DNA polymerase eta isoform 1Homo sapiens (human)Potency79.43280.100028.9256213.3130AID588591
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency100.00000.050127.073689.1251AID588590
Rap guanine nucleotide exchange factor 4Homo sapiens (human)Potency39.81073.981146.7448112.2020AID720708
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
PSMD14 proteinHomo sapiens (human)IC50 (µMol)17.90001.300021.871550.9000AID602368
TPA: prothrombinBos taurus (cattle)IC50 (µMol)13.70004.810036.743277.4000AID602369
72 kDa type IV collagenase isoform 1 preproproteinHomo sapiens (human)IC50 (µMol)100.00005.790038.963378.4000AID602361
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]

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
dual specificity tyrosine-phosphorylation-regulated kinase 1ARattus norvegicus (Norway rat)AC502.98700.00564.693226.6940AID588345
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (15)

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)
adaptive immune responseRap guanine nucleotide exchange factor 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 4Homo sapiens (human)
calcium-ion regulated exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of exocytosisRap guanine nucleotide exchange factor 4Homo sapiens (human)
insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
positive regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of synaptic vesicle cycleRap guanine nucleotide exchange factor 4Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 4Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

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)
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
protein-macromolecule adaptor activityRap guanine nucleotide exchange factor 4Homo sapiens (human)
small GTPase bindingRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

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)
cytosolRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseRap guanine nucleotide exchange factor 4Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (18)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (5.56)18.7374
1990's3 (16.67)18.2507
2000's4 (22.22)29.6817
2010's7 (38.89)24.3611
2020's3 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 38.58

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index38.58 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.93 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (38.58)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (5.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.910ether;
tertiary amino compound		anti-allergic agent;
antidyskinesia agent;
antiemetic;
antiparkinson drug;
antipruritic drug;
antitussive;
H1-receptor antagonist;
local anaesthetic;
muscarinic antagonist;
oneirogen;
sedative
harmaline
Harmaline: A beta-carboline alkaloid isolated from seeds of PEGANUM.. harmaline : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7 and has been reduced across the 3,4 bond.		6.58111harmala alkaloidoneirogen
harmalol
harmalol: inhibitor of rat liver microsomal UDP-glucuronyltransferase; RN given refers to parent cpd; structure. harmalol : A harmala alkaloid in which the harman skeleton is hydroxy-substituted at C-7 and has been reduced across the 3,4 bond.		2.0110harmala alkaloidalgal metabolite;
EC 1.4.3.4 (monoamine oxidase) inhibitor
n,n-dimethyltryptamine
N,N-Dimethyltryptamine: An N-methylated indoleamine derivative and serotonergic hallucinogen which occurs naturally and ubiquitously in several plant species including Psychotria veridis. It also occurs in trace amounts in mammalian brain, blood, and urine, and is known to act as an agonist or antagonist of certain SEROTONIN RECEPTORS.. N,N-dimethyltryptamine : A tryptamine derivative having two N-methyl substituents on the side-chain.		6.271tryptamine alkaloid;
tryptamines
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified		1.9610isoquinolines
catechin
Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.		2.0510catechinantioxidant;
plant metabolite
harmol
harmol: harmol is oxidized form of alkaloid harmolol; RN given refers to parent cpd; structure		4.3411harmala alkaloid
tetrahydroharmane
[no description available]		2.0110
tryptoline
tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure		2.0110beta-carbolines
procyanidin
Proanthocyanidins: Dimers and oligomers of flavan-3-ol units (CATECHIN analogs) linked mainly through C4 to C8 bonds to leucoanthocyanidins. They are structurally similar to ANTHOCYANINS but are the result of a different fork in biosynthetic pathways.		2.0510proanthocyanidin
4,9-dihydro-7-methoxy-3h-pyrido(3,4b)indole
4,9-dihydro-7-methoxy-3H-pyrido(3,4b)indole: structure given in first source		2.0110
1-methyl-6-methoxy-dihydro-beta-carboline
[no description available]		2.0110
harmine
Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.		6.67121harmala alkaloidanti-HIV agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
metabolite
phosphorus
Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.		2.910monoatomic phosphorus;
nonmetal atom;
pnictogen		macronutrient
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Degenerative Diseases, Central Nervous System
[description not available]		02.0510
Idiopathic Parkinson Disease
[description not available]		02.0510
Parkinson Disease
A progressive, degenerative neurologic disease characterized by a TREMOR that is maximal at rest, retropulsion (i.e. a tendency to fall backwards), rigidity, stooped posture, slowness of voluntary movements, and a masklike facial expression. Pathologic features include loss of melanin containing neurons in the substantia nigra and other pigmented nuclei of the brainstem. LEWY BODIES are present in the substantia nigra and locus coeruleus but may also be found in a related condition (LEWY BODY DISEASE, DIFFUSE) characterized by dementia in combination with varying degrees of parkinsonism. (Adams et al., Principles of Neurology, 6th ed, p1059, pp1067-75)		02.0510
Neurodegenerative Diseases
Hereditary and sporadic conditions which are characterized by progressive nervous system dysfunction. These disorders are often associated with atrophy of the affected central or peripheral nervous system structures.		02.0510
Depression, Endogenous
[description not available]		04.3411
Anxiety
Feelings or emotions of dread, apprehension, and impending disaster but not disabling as with ANXIETY DISORDERS.		04.3411
Depressive Disorder
An affective disorder manifested by either a dysphoric mood or loss of interest or pleasure in usual activities. The mood disturbance is prominent and relatively persistent.		04.3411