| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Opioid Receptor (mu-1; competitive binding); GABA Receptor (low-affinity inhibitory).
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|---|---|
| ln Vitro |
(S)-Laudanosine interacts with multiple receptor systems in vitro. It binds to micro-1 opioid receptor competitively, and inhibits the low-affinity GABA receptor. It also shows interactions with nicotinic acetylcholine receptors (nAChRs). The compound exhibits analgesic effects at lower concentrations and pro-convulsant or seizure-inducing activity at higher concentrations. It modulates neurotransmitter release in the central nervous system and may alter synaptic transmission by affecting GABAergic and opioidergic pathways.
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| ln Vivo |
In vivo, (S)-Laudanosine crosses the blood-brain barrier and at low doses produces analgesic effects. At higher plasma concentrations, it causes CNS excitation including euphoria and seizures. In the cardiovascular system, high plasma concentrations lead to hypotension and bradycardia. Animal studies in mice, rats, and dogs have shown dose-dependent neurological and cardiovascular effects. It is a metabolite of atracurium and cisatracurium and may accumulate in patients with renal or hepatic dysfunction receiving prolonged neuromuscular blockade.
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| Enzyme Assay |
No standardized in vitro receptor binding assay protocols specifically for (S)-Laudanosine are publicly available. For exploratory research, radioligand displacement assays using membrane preparations from cells expressing recombinant opioid receptors (mu, delta, kappa) with [3H]-DAMGO or [3H]-diprenorphine can be used. GABA receptor binding can be assessed using [3H]-muscimol (GABA-A) or [3H]-baclofen (GABA-B) displacement assays. Binding affinities (Ki or IC50 values) can be determined by incubating membranes with fixed radioligand concentrations and varying concentrations of (S)-Laudanosine (1 nM to 100 uM).
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| Cell Assay |
Cell-based assays for (S)-Laudanosine are not extensively standardized. For receptor functional studies, CHO or HEK-293 cells stably expressing human mu-opioid receptor can be used in cAMP accumulation assays. Cells are treated with forskolin (10 uM) to stimulate cAMP production, then treated with (S)-Laudanosine (0.1-100 uM) to measure inhibition of cAMP (Gi signaling). Calcium flux assays using fluorescent dyes (e.g., Fluo-4) can assess GABA-A receptor modulation in neuronal cell lines (e.g., SH-SY5Y) expressing endogenous receptors. Neuronal activity can be assessed by whole-cell patch-clamp electrophysiology in primary cortical neuron cultures.
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| Animal Protocol |
In vivo animal protocols for (S)-Laudanosine typically involve intravenous administration in rodents (mice, rats) or dogs at doses ranging from 1-20 mg/kg. Neurological effects (seizure activity, sedation, analgesic response) are monitored for 0-120 minutes post-dosing. Electroencephalography (EEG) may be used to record seizure activity. For analgesic testing, tail-flick or hot-plate assays are performed. Cardiovascular parameters (heart rate, blood pressure) are monitored via telemetry or catheterization. In dogs, cardiovascular and neurological effects are characterized after IV injection. Plasma concentration-effect relationships are determined by serial blood sampling and LC-MS/MS analysis.
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| ADME/Pharmacokinetics |
(S)-Laudanosine has a plasma half-life of approximately 2-4 hours in humans after metabolism of atracurium/cisatracurium, though this varies substantially with renal and hepatic function. It crosses the blood-brain barrier. It is primarily metabolized in the liver and excreted in urine. High plasma concentrations can lead to CNS excitation (seizures) and cardiovascular effects (hypotension, bradycardia). In rodents, IV administration shows rapid distribution and clearance. The compound has a molecular weight of 357.44, XLogP of 2.8, and is soluble in DMSO (40-50 mg/mL). Storage: powder at -20degC (3 years), in-solvent at -80degC (6 months).
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| Toxicity/Toxicokinetics |
(S)-Laudanosine is known to cause seizures and CNS excitation at high plasma concentrations, mediated through GABA receptor antagonism. It produces hypotension and bradycardia at elevated levels in the cardiovascular system. In animal models (mice, rats), LD50 values are in the range of 30-60 mg/kg (IV). Atracurium and cisatracurium, which produce laudanosine as a metabolite, can cause laudanosine accumulation in patients with organ failure. Chronic toxicity is not well-defined. The compound is a research chemical and not a therapeutic product. It should be handled with appropriate safety precautions.
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| References |
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| Additional Infomation |
(S)-Laudanosine is a metabolite of the neuromuscular-blocking drugs atracurium (A794500) and cisatracurium (C496700). It was first isolated from opium poppy. In clinical anesthesia, laudanosine accumulation is a concern in patients with renal or hepatic failure receiving prolonged infusions, as it can cause seizures and CNS excitation. The compound is used as a reference standard and impurity reference in pharmaceutical quality control for neuromuscular blocking agents. It has not been developed as a standalone therapeutic agent. It is strictly for laboratory research and analytical reference use only.
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| Molecular Formula |
C21H27NO4
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|---|---|
| Molecular Weight |
357.44
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| Exact Mass |
357.194
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| CAS # |
2688-77-9
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| PubChem CID |
73397
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| Appearance |
White to off-white solid powder
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| Density |
1.111g/cm3
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| Boiling Point |
468.1ºC at 760mmHg
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| Flash Point |
131.2ºC
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| LogP |
3.431
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
26
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| Complexity |
434
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC
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| InChi Key |
KGPAYJZAMGEDIQ-KRWDZBQOSA-N
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| InChi Code |
InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1
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| Chemical Name |
(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
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| Synonyms |
(S)-Laudanine
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7977 mL | 13.9884 mL | 27.9767 mL | |
| 5 mM | 0.5595 mL | 2.7977 mL | 5.5953 mL | |
| 10 mM | 0.2798 mL | 1.3988 mL | 2.7977 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.
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