Page last updated: 2024-11-07

guvacoline

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

Description

guvacoline: nootropic agent from areca nut (Areca catechu L.); structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

guvacoline : The methyl ester of guvacine. [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]

FloraRankFlora DefinitionFamilyFamily Definition
ArecagenusA plant genus of the family ARECACEAE. Members contain ARECOLINE and CATECHIN. The leaves and nuts have been used as masticatories, stimulants, and astringents in traditional medicine. The common name of betel is also used for PIPER BETLE. The common name of catechu is sometimes used for ACACIA CATECHU.[MeSH]ArecaceaeThe palm family of order Arecales, subclass Arecidae, class Liliopsida.[MeSH]

Cross-References

ID SourceID
PubMed CID160492
CHEMBL ID268808
CHEBI ID80754
SCHEMBL ID3019132
MeSH IDM000594581

Synonyms (28)

Synonym
1,2,5,6-tetrahydro-3-pyridinecarboxylic acid methyl ester hydrochloride
guvacoline
CHEMBL268808 ,
chebi:80754 ,
495-19-2
methyl 1,2,5,6-tetrahydro-3-pyridinecarboxylate
1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
bdbm50024984
methyl 1,2,3,6-tetrahydropyridine-5-carboxylate
yt3of85p98 ,
unii-yt3of85p98
3-pyridinecarboxylic acid, 1,2,5,6-tetrahydro-, methyl ester
AKOS006326662
FT-0626846
FT-0626845
SCHEMBL3019132
methyl 1,2,5,6-tetrahydronicotinate
methyl 1,2,5,6-tetrahydropyridine-3-carboxylate
guvacine methyl ester
nicotinic acid, 1,2,5,6-tetrahydro-, methyl ester
3-(methoxycarbonyl)-1,2,5,6-tetrahydropyridine
DTXSID20197805
Q27149807
F14151
guvacine free base
498-96-4 (free base)
SB53050
EN300-261947
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
muscarinic agonistAny drug that binds to and activates a muscarinic cholinergic receptor.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role 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]

Drug Classes (7)

ClassDescription
beta-amino acid esterAn amino acid ester resulting from the formal condensation of the carboxy group of a beta-amino acid with the hydroxy group of an alcohol or phenol.
methyl esterAny carboxylic ester resulting from the formal condensation of a carboxy group with methanol.
enoate esterAn alpha,beta-unsaturated carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
tetrahydropyridine
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
alpha,beta-unsaturated carboxylic esterA carboxylic ester of general formula R(1)R(2)C=CR(3)-C(=O)OR(4) (R(4) =/= H) or R(1)C#C-C(=O)OR(2) (R(2) =/= H) in which the ester C=O function is conjugated to an unsaturated C-C bond at the alpha,beta position.
pyridine alkaloid
[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 (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)IC50 (µMol)30.00000.00052.773925.1700AID141542
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)IC50 (µMol)30.00000.00052.891925.1700AID141542
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)IC50 (µMol)30.00000.00052.747825.1700AID141542
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)IC50 (µMol)30.00000.00052.780225.1700AID141542
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)IC50 (µMol)30.00000.00053.314249.5000AID141542
[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)
Muscarinic acetylcholine receptor M1Rattus norvegicus (Norway rat)K app8.60920.00000.98246.2000AID142085; AID142087; AID142095; AID142096
Muscarinic acetylcholine receptor M3Rattus norvegicus (Norway rat)K app8.60920.00000.98246.2000AID142085; AID142087; AID142095; AID142096
Muscarinic acetylcholine receptor M4Rattus norvegicus (Norway rat)K app8.60920.00000.98246.2000AID142085; AID142087; AID142095; AID142096
Muscarinic acetylcholine receptor M5Rattus norvegicus (Norway rat)K app8.60920.00000.98246.2000AID142085; AID142087; AID142095; AID142096
Muscarinic acetylcholine receptor M2Rattus norvegicus (Norway rat)K app8.60920.00001.00846.2000AID142085; AID142087; AID142095; AID142096
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID142095Apparent binding affinity to rat cortical muscarinic acetylcholine receptor by the displacement of [3H]N-methylscopolamine1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Tetrahydropyridyloxadiazoles: semirigid muscarinic ligands.
AID72445Inhibition of GABA uptake from rat diencephalon-midbrain,1985Journal of medicinal chemistry, May, Volume: 28, Issue:5
Orally active and potent inhibitors of gamma-aminobutyric acid uptake.
AID141542Inhibition of binding of radioactive N-propylbenzilycholine mustard ([3H]-PrBCM) to rat brain membranes1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
A novel class of conformationally restricted heterocyclic muscarinic agonists.
AID142367Ratio of apparent binding affinities of NMS and Oxo-M1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Tetrahydropyridyloxadiazoles: semirigid muscarinic ligands.
AID142917Ratio of [3H]N-methylscopolamine (NMS) to [3H]oxotremorine (OXO) at muscarinic acetylcholine receptor from rat cortical homogenate.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis and muscarinic activities of 1,2,4-thiadiazoles.
AID141130Contraction of guinea pig ileum by muscarinic AChR activation, which could be inhibited by application of atropine1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
A novel class of conformationally restricted heterocyclic muscarinic agonists.
AID142096Apparent binding affinity at rat cortical muscarinic acetylcholine receptor by the displacement of [3H]oxotremorine-M.1991Journal of medicinal chemistry, Mar, Volume: 34, Issue:3
Tetrahydropyridyloxadiazoles: semirigid muscarinic ligands.
AID142085Ability to displace radioligand [3H]N-methylscopolamine (NMS) at muscarinic acetylcholine receptor from rat cortical homogenate.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis and muscarinic activities of 1,2,4-thiadiazoles.
AID26318Dissociation constant (pKa)1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
A novel class of conformationally restricted heterocyclic muscarinic agonists.
AID142087Affinity to displace radioligand [3H]oxotremorine (OXO) at muscarinic acetylcholine receptor from rat cortical homogenate.1990Journal of medicinal chemistry, Jul, Volume: 33, Issue:7
Synthesis and muscarinic activities of 1,2,4-thiadiazoles.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (18.18)18.7374
1990's2 (18.18)18.2507
2000's0 (0.00)29.6817
2010's6 (54.55)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.24

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 Index25.24 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.24)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]