nepetalactone

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

Description

Nepetalactone is a naturally occurring iridoid found in catnip (Nepeta cataria) and other plants. It is known for its psychoactive effects on cats, causing a characteristic response including rubbing, rolling, and licking. The compound is thought to act as an agonist for the olfactory receptor in the cat's nose. Nepetalactone has also been studied for its potential antimicrobial, insecticidal, and anti-inflammatory properties. It is synthesized in plants through a complex series of biosynthetic steps involving the terpenoid pathway. The unique biological effects of nepetalactone make it an interesting subject of research, particularly in the areas of animal behavior, drug discovery, and natural product chemistry.'

nepetalactone: RN given for (4aS-(4aalpha,7alpha,7aalpha))-isomer; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trans-cis-nepetalactone : A cyclopentapyran that is (4aS,7aS)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by an oxo group and at positions 4 and 7 by methyl groups, respectively (the 4aS,7S,7aS-diastereomer). An iridoid monoterpenoid isolated from several Nepeta plant species. It exhibits potent repellant activity against house dust mites and mosquitoes. [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]

Cross-References

ID Source	ID
PubMed CID	92770
SCHEMBL ID	4996253
MeSH ID	M0297667

Synonyms (23)

Synonym
cyclopenta[c]pyran-1(4ah)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-
nepetalactone
nepetalactone, 4aa,7a,7ab
5,6,7,7a-tetrahydro-4,7-dimethyl-cyclopenta(c)pyran-1(4ah)-one
cyclopenta(c)pyran-1-(4ah)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-
md(sub 1) 84
490-10-8
4,7-dimethyl-5,6,7,7a-tetrahydro-4ah-cyclopenta[c]pyran-1-one
cyclopentanecarboxylic acid, 2-(2-hydroxy-1-methylvinyl)-5-methyl-, delta-lactone
mdi 84
SCHEMBL4996253
trans-cis-nepetalactone
cis,trans-nepetalactone
nepetalactone, cis-trans-
cyclopenta[c]pyran-1(4ah)-one, 5,6,7,7a-tetrahydro-4,7-dimethyl-, [4as-(4a.alpha.,7.alpha.,7a.alpha.)]-
cyclopenta[c]pyran-1(4ah)-one, 5,6,7,7a-tetrahydro-4,7.alpha.-dimethyl-, (+)-
trans-nepetalactone
cis-trans nepetalactone
4,7-dimethyl-5,6,7,7a-tetrahydrocyclopenta[c]pyran-1(4ah)-one
DTXSID80862022
STARBLD0009034
PD166389
AKOS040753248

Research Excerpts

Overview

Nepetalactone is an attractant to feline animals causing euphoric effects. It is a repellent to mosquitoes and cockroaches.

Excerpt	Reference	Relevance
"Nepetalactone is an attractant to feline animals causing euphoric effects, while it is a repellent to mosquitoes and cockroaches."	( Density-functional theory of the catnip molecule, nepetalactone. Badshah, SL; Jehan, R, 2022)	1.7

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (42)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.38)	18.7374
1990's	1 (2.38)	18.2507
2000's	13 (30.95)	29.6817
2010's	19 (45.24)	24.3611
2020's	8 (19.05)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 54.22

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

Metric	This Compound (vs All)
Research Demand Index	54.22 (24.57)
Research Supply Index	3.83 (2.92)
Research Growth Index	5.85 (4.65)
Search Engine Demand Index	84.11 (26.88)
Search Engine Supply Index	2.04 (0.95)

This Compound (54.22)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	45 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group.	2.05	1	alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound	amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite
eucalyptol [no description available]	2.77	3
deet N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.	2.95	4	benzamides; monocarboxylic acid amide	environmental contaminant; insect repellent; xenobiotic
skatole [no description available]	2.02	1	methylindole	human metabolite; mammalian metabolite
cyclohexanol Cyclohexanols: Monohydroxy derivatives of cyclohexanes that contain the general formula R-C6H11O. They have a camphorlike odor and are used in making soaps, insecticides, germicides, dry cleaning, and plasticizers.. cyclohexanols : An alcohol in which one or more hydroxy groups are attached to a cyclohexane skeleton.	2.45	2	cyclohexanols; secondary alcohol	solvent
nonane iotrochotin: toxin from the Caribbean sponge Iotrochota birotulata, which selectively permeabilizes synaptosomes. nonane : A straight chain alkane composed of 9 carbon atoms.	2.02	1	alkane	plant metabolite; volatile oil component
pelargonic acid pelargonic acid: K salt acts as cariostatic agent; RN given refers to parent cpd; structure. nonanoic acid : A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.	2.02	1	medium-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; antifeedant; Daphnia magna metabolite; plant metabolite
cyclopentane Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.	4.84	32	cycloalkane; cyclopentanes; volatile organic compound	non-polar solvent
1-tridecene [no description available]	2.02	1	acyclic olefin
nonanal nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.	2.02	1	medium-chain fatty aldehyde; n-alkanal; saturated fatty aldehyde	human metabolite; plant metabolite
alkenes [no description available]	2.02	1
dolichodial dolichodial: isolated from walkingstick, Anisomorpha buprestoides. dolichodial : A dialdehyde that is cyclopentanecarbaldehyde substituted by a methyl group at position 2 and a 3-oxo-prop-1-en-2yl group at position 5. It has been found to occur in pheromones of insects such as aphids.	2.04	1	dialdehyde; iridoid monoterpenoid; olefinic compound	animal metabolite; plant metabolite; volatile oil component
iridoids Iridoids: A type of MONOTERPENES, derived from geraniol. They have the general form of cyclopentanopyran, but in some cases, one of the rings is broken as in the case of secoiridoid. They are different from the similarly named iridals (TRITERPENES).	8.51	7
sesquiterpenes [no description available]	2.47	2
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.46	2
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	2.05	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	1.99	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.06	1
nepetalactol nepetalactol: a sex pheromone isolated from the potato aphid, Macrosiphum euphorbiae; structure in first source. cis-trans-nepetalactol : A cyclopentapyran that is 1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran substituted at position 1 by a hydroxy group and at positions 4 and 7 by methyl groups (the 4aS,7S,7aR-diastereomer)	8.29	6	cyclopentapyran; lactol
isolongifolenone isolongifolenone: natural compound found in the Tauroniro tree (Humiria balsamifera) of South America, Insecticide for mosquito control	2.07	1
phosphinothricin phosphinothricin: RN given refers to parent cpd with unspecified isomeric designation; structure. phosphinothricin(1-) : Conjugate base of phosphinothricin arising from deprotonation of the phosphinate function.	7.21	1	organic anion
ss220 SS220: Insect Repellent	2.45	2
piperidines Piperidines: A family of hexahydropyridines.	2.45	2

Condition	Relationship Strength	Studies
Dehydration The condition that results from excessive loss of water from a living organism.	7.25	1
Insect Bites [description not available]	2.44	2
Insect Bites and Stings Bites and stings inflicted by insects.	2.44	2

chemdatabank.com