| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| 1g |
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| 2g |
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| Other Sizes |
Purity: ≥98%
| Targets |
MAO (monoamine oxidase)
Phenelzine Sulfate targets both monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) isoforms. It acts as an irreversible inhibitor, meaning it forms a covalent bond with the enzyme, leading to its permanent inactivation. The Ki values for MAO-A and MAO-B are 47-163 nM and 15-94 nM, respectively. By inhibiting MAO, it prevents the breakdown of monoamine neurotransmitters such as norepinephrine, dopamine, and serotonin, leading to increased synaptic concentrations of these neurotransmitters. In addition to MAO inhibition, Phenelzine is the only clinically available MAOI that robustly elevates brain levels of GABA through inhibition of GABA transaminase (GABA-T). This dual mechanism contributes to its unique clinical profile. |
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| ln Vitro |
eroxynitrite is a reactive nitrogen species produced in the intravascular compartment from superoxide anion and nitric oxide. Peroxynitrite destroys blood plasma proteins and membranes of red blood cells and of platelets. This explains why excessive production of peroxynitrite contributes to diseases and to ageing. Therapeutics that antagonize peroxynitrite may delay ageing and the progression of disease. We developed an in vitro assay that allows the investigation of the oxidative damage caused by peroxynitrite in the intravascular compartment. This assay correlates the damage with the rate of formation of protein carbonyl groups, 3-nitrotyrosine (3-NT) and thiobarbituric acid reactive substances. Using this assay, we evaluated the ability of phenelzine, a scavenger of reactive aldehydes, to antagonize the effects of peroxynitrite. Herein, we showed that phenelzine significantly decreased the lipid peroxidative damage caused by peroxynitirite in blood plasma and platelets. Moreover, it inhibited carbonyl group and 3-NT formation in blood plasma and platelet proteins[1].
In vitro, Phenelzine is an inhibitor of monoamine oxidase (MAO) with an IC50 of 0.9 μM using rat brain mitochondrial preparations. It potentiates the effects of tryptamine on isolated rat fundus with an EC50 of 90 nM. This potentiation is a consequence of MAO inhibition, as tryptamine is a substrate for MAO. Its ability to inhibit GABA-T has also been characterized in vitro, contributing to its unique neurochemical profile. |
| ln Vivo |
In mice, intraperitoneal injection of phenelzine immediately after severe thoracic compression, and thereafter once daily for 6 weeks, improved hind limb function, reduced astrogliosis and promoted axonal regrowth/sprouting at 4 and 5 weeks after spinal cord injury compared to vehicle control-treated mice. Phenelzine application upregulated L1 expression in the spinal cord and stimulated the cognate L1-mediated intracellular signaling cascades in the spinal cord tissue. Phenelzine-treated mice showed decreased levels of pro-inflammatory cytokines, such as interleukin-1β, interleukin-6, and tumor necrosis factor-α in the injured spinal cord during the acute phase of inflammation[2].
In vivo, Phenelzine increases tryptamine toxicity in mice, with LD50 values of 85 and 500 mg/kg in the presence and absence of phenelzine, respectively. This demonstrates its potentiation of tryptamine's effects through MAO inhibition. At a dose of 20 mg/kg, it increases GABA, dopamine, serotonin (5-HT), and norepinephrine levels in the hippocampus and cortex of socially isolated rats. At a dose of 30 mg/kg, it increases 5-HT levels in the ventral horn of the spinal cord, improves gross motor ability in a rotarod test, and increases locomotor activity in an open field test in mice with experimental autoimmune encephalomyelitis. These findings highlight its broad neurochemical and behavioral effects. |
| Enzyme Assay |
This study developed an in vitro assay that allows the investigation of the oxidative damage caused by peroxynitrite in the intravascular compartment. This assay correlates the damage with the rate of formation of protein carbonyl groups, 3-nitrotyrosine (3-NT) and thiobarbituric acid reactive substances. Using this assay, this study evaluated the ability of phenelzine, a scavenger of reactive aldehydes, to antagonize the effects of peroxynitrite. Herein, this study showed that phenelzine significantly decreased the lipid peroxidative damage caused by peroxynitirite in blood plasma and platelets[1].
In vitro enzyme/receptor binding studies for Phenelzine Sulfate are performed using enzyme activity assays. In these assays, MAO-A or MAO-B is incubated with a substrate, such as kynuramine or serotonin, in the presence of varying concentrations of the inhibitor. The enzyme's activity is measured by detecting the production of the deaminated metabolite, and the IC50 or Ki value is calculated. These assays are essential for confirming its mechanism as an irreversible MAO inhibitor. Similar assays can be performed to characterize its inhibition of GABA-T. |
| Cell Assay |
In vitro cellular assays for Phenelzine Sulfate are used to study its effects on neurotransmitter levels. In these experiments, neuronal cell cultures or brain slices are treated with the compound, and the levels of neurotransmitters (e.g., serotonin, dopamine, norepinephrine, GABA) are measured by HPLC or other analytical techniques. These assays confirm that MAO inhibition by Phenelzine leads to increased neurotransmitter concentrations in a cellular context.
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| Animal Protocol |
In mice, intraperitoneal injection of phenelzine immediately after severe thoracic compression, and thereafter once daily for 6 weeks, improved hind limb function, reduced astrogliosis and promoted axonal regrowth/sprouting at 4 and 5 weeks after spinal cord injury compared to vehicle control-treated mice[2].
In vivo animal studies for Phenelzine Sulfate are conducted in rodent models. In these studies, animals are treated with the compound, and behavioral, neurochemical, and physiological endpoints are measured. For example, its effects on tryptamine toxicity are assessed by administering tryptamine and measuring lethality. Its effects on neurotransmitter levels are measured in brain tissue. Behavioral tests, such as the rotarod and open field tests, are used to assess motor function and locomotor activity. These studies are critical for understanding its pharmacological profile and potential therapeutic applications. |
| ADME/Pharmacokinetics |
Pharmacokinetic properties of Phenelzine Sulfate include its high aqueous solubility (47 mg/mL), which simplifies in vivo dosing formulation. It has a molecular weight of 234.28 g/mol and a molecular formula of C8H14N2O4S. It is soluble in DMSO. As an irreversible MAOI, its pharmacodynamic effect outlasts its presence in the body, as new enzyme synthesis is required to restore MAO activity. Specific data on its half-life and metabolism are not detailed in the provided sources.
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| Toxicity/Toxicokinetics |
Toxicological data for Phenelzine Sulfate are derived from its clinical use as an antidepressant. Common side effects include orthostatic hypotension, weight gain, sexual dysfunction, and insomnia. Its use is associated with significant dietary restrictions to avoid hypertensive crises caused by the ingestion of tyramine-rich foods. It is contraindicated in patients with liver disease, pheochromocytoma, and those taking other serotonergic agents. Its safety profile is well-established, but its use requires careful medical supervision.
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| References |
[1]. Phenelzine reduces the oxidative damage induced by peroxynitrite in plasma lipids and proteins. Arch Physiol Biochem. 2018 Dec;124(5):418-423.
[2]. Phenelzine, a small organic compound mimicking the functions of cell adhesion molecule L1, promotes functional recovery after mouse spinal cord injury. Restor Neurol Neurosci . 2018;36(4):469-483. doi: 10.3233/RNN-170808. |
| Additional Infomation |
Phenelzine sulfate is an organic molecular entity. It is a hydrazine derivative and a potent, non-selective monoamine oxidase (MAO) inhibitor with anxiolytic and antidepressant effects. Phenelzine sulfate irreversibly binds to MAO, thereby blocking the oxidative deamination of monoamines, leading to increased concentrations of biogenic amines in the brain and reduced catabolism of monoamine neurotransmitters (norepinephrine and serotonin). Furthermore, Phenelzine exerts its anxiolytic effect by increasing GABA levels in the caudate-putamen and nucleus accumbens through its main metabolite, phenethylmethylenehydrazine (PEH). Monoamine oxidase inhibitors are used to treat depression and phobias, including panic attacks. See also: Phenelzine (with active moiety).
Phenelzine Sulfate is a non-selective, irreversible MAO inhibitor used as an antidepressant and anxiolytic. Its CAS number is 156-51-4. It is marketed under the brand name Nardil. Its unique pharmacology, including the inhibition of GABA-T, distinguishes it from other MAOIs. It is one of the few remaining MAOIs still in regular clinical use. Its clinical utility is limited by its side effect profile and dietary restrictions, but it remains a valuable option for treatment-resistant depression and atypical depression. |
| Molecular Formula |
C8H12N2.H2O4S
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|---|---|
| Molecular Weight |
234.27276
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| Exact Mass |
234.067
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| Elemental Analysis |
C, 41.02; H, 6.02; N, 11.96; O, 27.32; S, 13.69
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| CAS # |
156-51-4
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| Related CAS # |
Phenelzine-d5 sulfate;1219798-40-9
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| PubChem CID |
61100
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| Appearance |
White to off-white solid powder
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| Boiling Point |
497.4ºC at 760 mmHg
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| Flash Point |
254.6ºC
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| Vapour Pressure |
1.04E-10mmHg at 25°C
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| LogP |
2.211
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
159
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| Defined Atom Stereocenter Count |
0
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| SMILES |
NNCCC1=CC=CC=C1.O=S(O)(O)=O
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| InChi Key |
RXBKMJIPNDOHFR-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H12N2.H2O4S/c9-10-7-6-8-4-2-1-3-5-8;1-5(2,3)4/h1-5,10H,6-7,9H2;(H2,1,2,3,4)
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| Chemical Name |
2-phenylethylhydrazine;sulfuric acid
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| Synonyms |
W-1544; W1544; W 1544; Phenelzine sulfate; 156-51-4; PHENELZINE SULFATE SALT; Estinerval; Kalgan; Phenelzine sulphate; Phenelzine (sulfate); Nardelzine; Nardil
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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 Note: Please store this product in a sealed and protected environment, 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)
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| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~426.86 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (8.88 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 20.8 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: ≥ 2.08 mg/mL (8.88 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 20.8 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: ≥ 2.08 mg/mL (8.88 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 | 4.2686 mL | 21.3429 mL | 42.6858 mL | |
| 5 mM | 0.8537 mL | 4.2686 mL | 8.5372 mL | |
| 10 mM | 0.4269 mL | 2.1343 mL | 4.2686 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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