| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Nepetalactone primarily targets olfactory receptors in the feline olfactory epithelium, where it binds to specific G-protein-coupled receptors. Upon nasal exposure, it triggers a series of neurological responses affecting the amygdala, hypothalamus, and other brain regions associated with emotion and behavior. In insects, nepetalactone acts as a pheromone receptor agonist, particularly in aphids, where it modulates sexual behavior. Its antibacterial and antifungal activities are thought to involve disruption of microbial cell membrane integrity, though the precise molecular targets remain to be fully characterized.
|
|---|---|
| ln Vitro |
In vitro, nepetalactone demonstrates moderate to good antibacterial activity against various bacterial strains, including both Gram-positive and Gram-negative species, primarily through membrane-disrupting mechanisms. It also exhibits antifungal properties against common pathogenic fungi. Additionally, nepetalactone shows analgesic activity in cell-based pain models, likely mediated through opioid receptor-related pathways. The compound's insect repellent and attractant activities have been characterized in behavioral assays using insect cells and tissue preparations, confirming its dual function as both a pheromone and a repellent depending on concentration and species.
|
| ln Vivo |
In vivo, nepetalactone is well-known for its psychoactive effects in domestic cats, inducing behaviors such as rubbing, rolling, vocalization, and hyperactivity following inhalation. Rodent studies have demonstrated sedative and anxiolytic-like properties at certain doses, suggesting potential applications for stress-related conditions. In insect models, nepetalactone functions as an aphid sex pheromone and a repellent against mosquitoes and other pests. Analgesic effects have been confirmed in rodent pain models, supporting its traditional use as a mild pain reliever. However, further systematic in vivo pharmacological characterization is ongoing.
|
| Enzyme Assay |
A typical non-cellular binding assay for nepetalactone involves receptor-binding studies using membrane preparations from olfactory tissues. Membranes are incubated with increasing concentrations of radiolabeled nepetalactone in binding buffer (50 mM Tris-HCl, pH 7.4) for 60 min at room temperature. Non-specific binding is determined using excess unlabeled nepetalactone. Bound and free ligands are separated by rapid filtration through glass fiber filters, followed by scintillation counting. Saturation binding curves are analyzed to determine Kd and Bmax values. Competition binding assays using unlabeled compounds are performed to evaluate binding selectivity and affinity (adapted from standard GPCR binding protocols).
|
| Cell Assay |
In vitro cellular assays for nepetalactone typically use primary neuronal cultures or neuroblastoma cell lines to assess neuroactivity. Cells are seeded in 96-well plates and treated with nepetalactone at concentrations ranging from 1 uM to 100 uM for various durations (6-48 hours). Cellular viability is evaluated using MTT or resazurin-based assays. Neuronal activation is assessed by measuring intracellular calcium flux using fluorescent calcium indicators or by monitoring action potential firing via patch-clamp electrophysiology. For antibacterial activity, standard broth microdilution assays are performed in Mueller-Hinton broth to determine minimum inhibitory concentrations (MICs) against test bacterial strains following CLSI guidelines.
|
| Animal Protocol |
In vivo animal studies for nepetalactone commonly use feline or rodent models. For behavioral studies in cats, nepetalactone is administered via inhalation from a cotton ball containing the compound (typically 10-100 mg) placed near the animal, and behaviors are recorded and scored over 15-30 min. In rodent studies, nepetalactone is administered orally (1-50 mg/kg) or intraperitoneally, followed by behavioral assessments such as open field test, elevated plus maze, and tail flick test for analgesia. For antimicrobial efficacy, mouse models of infection are used, with nepetalactone administered intraperitoneally (10-100 mg/kg) 1 h prior to bacterial challenge. All studies require appropriate ethical approval and humane endpoints.
|
| ADME/Pharmacokinetics |
The pharmacokinetic properties of nepetalactone are characterized by rapid absorption and extensive metabolism. In silico ADMET modeling combined with in vitro metabolism assays using rat and human liver microsomes and UHPLC-MS/MS metabolite characterization reveals that nepetalactone undergoes rapid phase I (oxidative) and phase II (conjugative) metabolism in both species. The compound has moderate predicted oral bioavailability and is expected to be widely distributed with a volume of distribution consistent with lipophilic compounds. Elimination occurs primarily via hepatic metabolism, with minimal renal excretion of the parent compound. Further clinical pharmacokinetic data are currently limited.
|
| Toxicity/Toxicokinetics |
Toxicological evaluation of nepetalactone has been conducted primarily in rodent species. The oral LD50 in mice and rats ranges from approximately 300-1,500 mg/kg, indicating low acute toxicity. In subchronic toxicity studies, nepetalactone did not produce significant organ toxicity at moderate doses (≤100 mg/kg/day). No genotoxicity was observed in standard Ames tests or micronucleus assays. Skin and eye irritation potential is minimal. The compound is generally recognized as safe for its intended uses in pet products and biopesticides. However, high doses may cause mild sedation and gastrointestinal disturbances. Reproductive and developmental toxicity studies are limited.
|
| References | |
| Additional Infomation |
Nepetalactone (cis-trans) is a cyclopentanopyran compound with the structure (4aS,7aR)-1,4a,5,6,7,7a-hexahydrocyclopentano[c]pyran, with a carbonyl group substituted at position 1 and methyl groups substituted at positions 4 and 7 (4aS,7S,7aR-diastereomers). It is an iridoid monoterpene isolated from various Nepeta species. It is an aphid sex pheromone and cat attractant, and possesses antibacterial, antifungal, and analgesic effects. It functions as a pheromone, plant metabolite, insect attractant, analgesic, anthelmintic, antibacterial, and antifungal agent. It is an iridoid monoterpene and a cyclopentanopyran compound. The cis-trans isomer Nepetalactone has been reported in Nepeta tuberosa, Nepeta cataria, and Nepeta racemosa.
4aalpha,7alpha,7aalpha-Nepetalactone has not been approved for human therapeutic use as a drug product, but it is widely used in consumer products as a natural feline attractant and enrichment agent in cat toys and scratching posts. Its mechanism of action in cats involves binding to olfactory receptors, leading to activation of the limbic system and behavioral changes. Ongoing research is exploring its potential for human applications, including anxiety and insomnia treatment, due to its sedative and anxiolytic properties in preclinical models. No Phase II/III clinical trials have been registered for this compound as a pharmaceutical. For reference use only; not for human therapeutic administration. |
| Molecular Weight |
166.22
|
|---|---|
| Exact Mass |
166.099
|
| CAS # |
21651-62-7
|
| PubChem CID |
161367
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
1.0±0.1 g/cm3
|
| Boiling Point |
270.6±19.0 °C at 760 mmHg
|
| Flash Point |
107.7±18.9 °C
|
| Vapour Pressure |
0.0±0.6 mmHg at 25°C
|
| Index of Refraction |
1.485
|
| LogP |
2.83
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
12
|
| Complexity |
242
|
| Defined Atom Stereocenter Count |
3
|
| SMILES |
O1C=C(C)[C@@]2([H])CC[C@H](C)[C@@]2([H])C1=O
|
| InChi Key |
ZDKZHVNKFOXMND-NBEYISGCSA-N
|
| InChi Code |
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)5-12-10(11)9(6)8/h5-6,8-9H,3-4H2,1-2H3/t6-,8+,9+/m0/s1
|
| Chemical Name |
(4aS,7S,7aR)-4,7-dimethyl-5,6,7,7a-tetrahydro-4aH-cyclopenta[c]pyran-1-one
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (601.61 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.0161 mL | 30.0806 mL | 60.1612 mL | |
| 5 mM | 1.2032 mL | 6.0161 mL | 12.0322 mL | |
| 10 mM | 0.6016 mL | 3.0081 mL | 6.0161 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
