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Metapramine 21730-16-5

Metapramine 21730-16-5

CAS No.: 21730-16-5

Metapramine (19560 RP) is an antidepressant agent of the tricyclic class of compounds. Metapramine inhibits the reuptake
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Metapramine (19560 RP) is an antidepressant agent of the tricyclic class of compounds. Metapramine inhibits the reuptake of norepinephrine without affecting the reuptake of serotonin or dopamine. Metapramine is a low-affinity antagonist of N-methyl-D-aspartic acid (NMDA) receptor complex channels.

Physicochemical Properties


Molecular Formula C16H18N2
Molecular Weight 238.32752
Exact Mass 238.147
CAS # 21730-16-5
PubChem CID 65700
Appearance Typically exists as solid at room temperature
Density 1.12g/cm3
Boiling Point 350.8ºC at 760mmHg
Flash Point 140.7ºC
Vapour Pressure 4.27E-05mmHg at 25°C
Index of Refraction 1.633
LogP 3.727
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 2
Rotatable Bond Count 1
Heavy Atom Count 18
Complexity 278
Defined Atom Stereocenter Count 0
SMILES

CNC1CC2=CC=CC=C2N(C)C2=CC=CC=C12

InChi Key YXVZOBVWVRFPTE-UHFFFAOYSA-N
InChi Code

InChI=1S/C16H18N2/c1-17-14-11-12-7-3-5-9-15(12)18(2)16-10-6-4-8-13(14)16/h3-10,14,17H,11H2,1-2H3
Chemical Name

N,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine
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 Vivo Mice treated with metapramine (19560 RP) (0–20 mg/kg; i.p.) exhibit analgesic effects [5].
Animal Protocol Animal/Disease Models: Male Swiss albino mouse [5]
Doses: 0-20 mg/kg
Route of Administration: intraperitoneal (ip) injection
Experimental Results: Jump latency, threshold voltage increased, writhing and tail flick latencies diminished, in a dose-dependent manner.
References

[1]. [Metapramine: antidepressant and psycho-stimulant]. Encephale. 1976;2(3):219-23.

[2]. [Metapramine: antidepressant and psycho-stimulant]. Encephale. 1976;2(3):219-23.

[3]. [Effects, in rats, of metapramine and carpipramine on the uptake of catecholamines and serotonin; relationship with 3H-imipramine binding]. C R Seances Soc Biol Fil. 1986;180(1):43-8.

[4]. Immediate effects of 14 non MAOI antidepressants in rats with spontaneous petit mal-like seizures. Prog Neuropsychopharmacol Biol Psychiatry. 1990;14(2):261-70.

[5]. The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors. Neuropharmacology. 1996;35(12):1703-7.

[6]. Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants. Pain. 1987 Dec;31(3):391-400. doi: 10.1016/0304-3959(87)90167-9.

Additional Infomation Metapramine is a dibenzooxazepine.

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 4.1959 mL 20.9793 mL 41.9586 mL
5 mM 0.8392 mL 4.1959 mL 8.3917 mL
10 mM 0.4196 mL 2.0979 mL 4.1959 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.