Physicochemical Properties
| Molecular Formula | C16H13CLN4S |
| Molecular Weight | 328.8192 |
| Exact Mass | 328.054 |
| CAS # | 40054-68-0 |
| PubChem CID | 12434325 |
| Appearance | Typically exists as Light yellow to yellow solid at room temperature |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 527.2±60.0 °C at 760 mmHg |
| Flash Point | 272.6±32.9 °C |
| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
| Index of Refraction | 1.752 |
| LogP | 3.39 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Heavy Atom Count | 22 |
| Complexity | 446 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | ClC1=C([H])C([H])=C([H])C([H])=C1C1C2C([H])=C(C([H])([H])C([H])([H])[H])SC=2N2C([H])=NN=C2C([H])([H])N=1 |
| InChi Key | NQSSWDKQLVBUQN-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C16H13ClN4S/c1-2-10-7-12-15(11-5-3-4-6-13(11)17)18-8-14-20-19-9-21(14)16(12)22-10/h3-7,9H,2,8H2,1H3 |
| Chemical Name | 7-(2-chlorophenyl)-4-ethyl-3-thia-1,8,11,12-tetrazatricyclo[8.3.0.02,6]trideca-2(6),4,7,10,12-pentaene |
| Synonyms | Metizolam; Desmethyletizolam; 40054-68-0; K1C6XI9LLX; Metizolam [NFLIS-DRUG]; 4-(2-Chlorophenyl)-2-ethyl-6H-thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine; DTXSID101032847; 6H-Thieno(3,2-f)(1,2,4)triazolo(4,3-a)(1,4)diazepine, 4-(2-chlorophenyl)-2-ethyl-; |
| 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) |
Biological Activity
| ln Vitro |
采用人肝微粒体（HLM）和受控给药尿液样本研究metizolam代谢。在HLM中，metizolam（10 μM）主要通过CYP3A4/5代谢为α-羟基metizolam和二氢二醇-metizolam。动力学分析显示α-羟基metizolam生成的Km = 18.2 μM，Vmax = 0.41 nmol/min/mg蛋白。[1] |
| ln Vivo |
In human urine after 1 mg oral dose, unmetabolized metizolam accounted for 0.3% of total excretion. Major metabolites: α-hydroxymetizolam glucuronide (23.6%), dihydrodiol-metizolam glucuronide (17.8%), and desmethylmetizolam (12.1%). Detection window in urine was 24-48 h. [1] Metizolam was detectable in hair (1-2 cm segments) at 2.7–22.1 pg/mg and in blood at 0.5–3.2 ng/mL after single recreational use. [2] |
| ADME/Pharmacokinetics |
Metizolam metabolism was studied using human liver microsomes (HLM) and urine samples from a controlled administration study. In HLM, metizolam (10 μM) was metabolized primarily by CYP3A4/5 to α-hydroxymetizolam and dihydrodiol-metizolam. Kinetic analysis showed Km = 18.2 μM and Vmax = 0.41 nmol/min/mg protein for α-hydroxymetizolam formation. [1] In human urine after 1 mg oral dose, unmetabolized metizolam accounted for 0.3% of total excretion. Major metabolites: α-hydroxymetizolam glucuronide (23.6%), dihydrodiol-metizolam glucuronide (17.8%), and desmethylmetizolam (12.1%). Detection window in urine was 24-48 h. [1] Metizolam was detectable in hair (1-2 cm segments) at 2.7–22.1 pg/mg and in blood at 0.5–3.2 ng/mL after single recreational use. [2] |
| Toxicity/Toxicokinetics |
Acute toxicity: Reported mouse oral LD50 ≈ 700 mg/kg (cited from external source, not experimentally determined). [1] No hepatotoxicity observed in case studies at recreational doses (0.5–2 mg). Plasma protein binding not quantified. [2] |
| References |
[1]. Detection of the designer benzodiazepine metizolam in urine and preliminary data on its metabolism. Drug Test Anal. 2017 Jul;9(7):1026-1033. [2]. Characterization of metizolam, a designer benzodiazepine, in alternative biological specimens. Toxicologie Analytique et Clinique. 2017 Feb; 29(1): 57-63. |
| Additional Infomation |
Metizolam is a thienodiazepine designer benzodiazepine with structural similarity to etizolam. It is not approved for medical use and is distributed as a "research chemical". [1] Forensic identification: Major urinary metabolites (α-hydroxymetizolam glucuronide and dihydrodiol-metizolam) serve as consumption markers. Hair analysis provides longer detection windows than urine. [2] |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0412 mL | 15.2059 mL | 30.4118 mL | |
| 5 mM | 0.6082 mL | 3.0412 mL | 6.0824 mL | |
| 10 mM | 0.3041 mL | 1.5206 mL | 3.0412 mL |