| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| 10mg |
|
||
| Other Sizes |
| Targets |
Cannabinoid receptor type 1 (CB1R). (S)-Methanandamide is a ligand for the CB1 receptor with a Ki of 173 nM. It is less potent than the (R)-isomer (R-Methanandamide) for binding to CB1 receptors. It shows poor binding to CB2 receptors, making it a relatively selective tool for studying CB1-mediated effects.
|
|---|---|
| ln Vitro |
In vitro, (S)-Methanandamide binds to the CB1 receptor with a Ki of 173 nM. It functionally inhibits electrically induced twitching responses in the isolated mouse vas deferens with an IC50 of 230 nM, a classic assay for measuring presynaptic CB1 receptor-mediated inhibition of neurotransmitter release. It is less potent than the R-isomer in this assay.
|
| ln Vivo |
In vivo, (S)-Methanandamide is used to study cannabinoid-induced behavioral effects. It has been shown to produce effects such as hypothermia, antinociception (analgesia), and reduced locomotor activity in mice, which are mediated primarily through CB1 receptor activation. However, due to its lower potency, higher doses are required compared to the (R)-isomer or other potent CB1 agonists like WIN 55,212-2.
|
| Enzyme Assay |
The binding affinity of (S)-Methanandamide is determined via a radioligand competition binding assay. Rat brain cortical membranes (rich in CB1 receptors) are incubated with the high-affinity CB1 agonist [3H]CP-55,940 and varying concentrations of the test compound. After incubation at 30degC for 60-90 minutes, the reaction is terminated by filtration, and bound radioactivity is counted to calculate the inhibition constant (Ki).
|
| Cell Assay |
The functional activity of (S)-Methanandamide can be measured by its ability to inhibit adenylyl cyclase, the canonical signaling pathway for CB1 receptors. CHO cells stably expressing human CB1R are pre-incubated with varying concentrations of (S)-Methanandamide in the presence of forskolin to stimulate cAMP production. After incubation, intracellular cAMP levels are quantified using a homogeneous time-resolved fluorescence (HTRF) assay kit, and the EC50 for inhibition is determined.
|
| Animal Protocol |
In a standard in vivo protocol, male ICR mice are injected intraperitoneally with (S)-Methanandamide (e.g., 10-40 mg/kg) suspended in a vehicle such as 1% Tween-80 in saline. After 30-60 minutes, antinociception is measured using the tail-flick or hot-plate test. Body temperature is measured using a rectal probe to assess hypothermia. Locomotor activity is measured using an open field chamber to assess cannabinoid-induced motor depression.
|
| ADME/Pharmacokinetics |
Specific pharmacokinetic data for (S)-Methanandamide is not detailed. However, a key property of the methanandamide series is metabolic stability. The addition of a methyl group at the carbon adjacent to the amide nitrogen makes these analogs resistant to hydrolysis by fatty acid amide hydrolase (FAAH), the primary enzyme that degrades anandamide, resulting in a significantly longer half-life in vivo compared to the natural endocannabinoid.
|
| Toxicity/Toxicokinetics |
No detailed toxicological data is provided. As a research chemical targeting CB1 receptors, potential adverse effects are related to its pharmacology and include catalepsy, hypothermia, memory impairment, and ataxia at high doses. The (S)-isomer is less potent than the (R)-isomer, which may contribute to a slightly different safety profile, but detailed LD50 data is not available.
|
| References | |
| Additional Infomation |
S-1 formamide is a carboxyimide acid.
(S)-Methanandamide is a crucial research tool for dissecting the structure-activity relationship of endocannabinoid analogs. The chirality at the carbon alpha to the amide nitrogen dramatically affects receptor binding affinity and functional potency; the (R)-isomer is significantly more potent (Ki ≈ 20 nM for CB1) than the (S)-isomer (Ki = 173 nM). This stereoselectivity is important for understanding the precise binding orientation of ligands within the CB1 receptor pocket. |
| Molecular Formula |
C23H39NO2
|
|---|---|
| Molecular Weight |
361.56
|
| Exact Mass |
361.298
|
| CAS # |
157182-50-8
|
| PubChem CID |
5283423
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.9±0.1 g/cm3
|
| Boiling Point |
529.0±50.0 °C at 760 mmHg
|
| Flash Point |
273.8±30.1 °C
|
| Vapour Pressure |
0.0±3.2 mmHg at 25°C
|
| Index of Refraction |
1.501
|
| LogP |
6.01
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
16
|
| Heavy Atom Count |
26
|
| Complexity |
436
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(N[C@H](CO)C)=O
|
| InChi Key |
SQKRUBZPTNJQEM-AQNSPSBUSA-N
|
| InChi Code |
InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m0/s1
|
| Chemical Name |
(5Z,8Z,11Z,14Z)-N-[(2S)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
|
| 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 |
| 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 (276.58 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.91 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 (6.91 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7658 mL | 13.8290 mL | 27.6579 mL | |
| 5 mM | 0.5532 mL | 2.7658 mL | 5.5316 mL | |
| 10 mM | 0.2766 mL | 1.3829 mL | 2.7658 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
