156-51-4

Basic information

• Product Name: PHENELZINE SULFATE SALT
• Synonyms: 2-PHENYLETHYLHYDRAZINE SULFATE;PHENELZINE SULFATE;PHENELZINE SULFATE SALT;PHENYLETHYLHYDRAZINE SULFATE;(2-phenylethyl)-hydrazinsulfate(1:1);1-hydrazino-2-phenylethanehydrogensulphate;2-phenylethylhydrazinedihydrogensulphate;2-phenylethylhydrazinehydrogensulphate
• CAS NO: 156-51-4
• Molecular Formula: 2C₈H₁₃N₂*O₄S
• Molecular Weight: 234.27
• EINECS: 205-856-0
• Product Categories: Monoamine oxidase inhibitor;Monoamine OxidaseEnzyme Inhibitors by Enzyme;Enzyme Inhibitors;L to;Neurotransmitter Metabolism;Amines;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Neurochemicals;Pharmaceuticals;AVIL
• Mol File: 156-51-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 166.5-167.5 °C
• Boiling Point: 497.4°C at 760 mmHg
• Flash Point: 254.6°C
• Appearance: /
• Vapor Pressure: 1.04E-10mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Freely soluble in water; practically insoluble in ethanol (96%) and in ether .
• Merck: 13,7300
• CAS DataBase Reference: PHENELZINE SULFATE SALT(CAS DataBase Reference)
• NIST Chemistry Reference: PHENELZINE SULFATE SALT(156-51-4)
• EPA Substance Registry System: PHENELZINE SULFATE SALT(156-51-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: MV8750000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 156-51-4(Hazardous Substances Data)

Usage

Description

Phenelzine Sulfate Salt, also known as Nardil, is a hydrazine derivative that functions as a non-selective and irreversible monoamine oxidase inhibitor (MAOI). It also inhibits GABA-transaminase (GABA-T), leading to a significant increase in brain GABA levels. Phenelzine Sulfate Salt is an effective antidepressant agent, characterized by its mechanism-based inactivation of the enzyme or its cofactor. It is a white powder or pearly platelets and is commonly known by its brand name, Nardil.

Uses

Used in Pharmaceutical Industry:
Phenelzine Sulfate Salt is used as an antihistaminic for the treatment of major depressive disorder (MDD) and other neural disorders. It acts as an antidepressant and anxiolytic, providing relief from depressive symptoms and anxiety.
Used in Antidepressant Applications:
Phenelzine Sulfate Salt is used as an antidepressant for treating major depressive disorder (MDD). It works by inhibiting the enzyme monoamine oxidase, which is responsible for breaking down neurotransmitters such as serotonin, norepinephrine, and dopamine. This inhibition leads to an increase in the levels of these neurotransmitters in the brain, thereby alleviating depressive symptoms.
Used in Anxiolytic Applications:
Phenelzine Sulfate Salt is used as an anxiolytic to help reduce anxiety and stress. By increasing the levels of GABA in the brain, it helps to promote a sense of calm and relaxation, making it useful for individuals suffering from anxiety disorders.
Used in Neurological Disorder Treatment:
Phenelzine Sulfate Salt is used as a treatment for various neurological disorders, including major depressive disorder (MDD) and other mood-related conditions. Its ability to inhibit monoamine oxidase and GABA-transaminase makes it a valuable tool in managing the symptoms of these disorders.

Originator

Nardil ,Parke Davis, US ,1959

Manufacturing Process

To a refluxing solution containing 147.5 grams of 85% hydrazine hydrate in 500 cc of ethanol was added, during a period of 5 hours, 92.5 grams of phenethylbromide (0.50 mol) in 150 cc of ethanol. Stirring and refluxing were continued for two hours. The ethanol was removed by distillation and the residue extracted repeatedly with ether. The ether was dried with potassium carbonate and the product base collected by distillation, BP 74°C/0.1 mm, yield 52.3 grams (77%). The base is reacted with sulfuric acid in propanol to give the sulfate.

Therapeutic Function

Psychostimulant

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Human systemic effects by ingestion: wakefulness, blood pressure lowering, constipation, hepatitis, fibrous hepatitis. Experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. Used as a drug for the treatment of depression. When heated to decomposition it emits very toxic fumes of SOx and NOx.

InChI:InChI=1/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)/p-2

Synthetic route

3-(pyridine-2-yl)-3-oxopropanenitrile (54123-21-6) + 2-phenethylhydrazine sulfate (156-51-4) → 2-phenethyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine (1316122-43-6)

Conditions	Yield
With triethylamine In ethanol for 2h; Inert atmosphere; Reflux;	87%
With triethylamine In ethanol at 20℃; for 2h; Inert atmosphere; Reflux;	87%

2-phenethylhydrazine sulfate (156-51-4) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → ethyl 3-amino-1-phenethyl-1H-pyrazole-4-carboxylate

Conditions	Yield
With sodium ethanolate In tetrahydrofuran; ethanol at 0℃; Inert atmosphere; regioselective reaction;	81%

gadolinium(III) sulfate hydrate + 2-phenethylhydrazine sulfate (156-51-4) → Gd(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Gd(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	75%

C21H31N9O5S + 2-phenethylhydrazine sulfate (156-51-4) → C29H44N12O5S

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃;	73%

2-phenethylhydrazine sulfate (156-51-4) + 4-(2-tert-butoxycarbonyl-2-oxo-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester (237421-80-6) → 4-[2-tert-butoxycarbonyl-2-(phenethyl-hydrazono)-ethyl]-5-oxo-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester

Conditions	Yield
With sodium acetate In methanol for 2h; Ambient temperature;	70%

2Sm(3+)*3SO4(2-)*99H2O = Sm2(SO4)3*99H2O + 2-phenethylhydrazine sulfate (156-51-4) → Sm(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Sm(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	70%

2Eu(3+)*3SO4(2-)*99H2O = Eu2(SO4)3*99H2O + 2-phenethylhydrazine sulfate (156-51-4) → Eu(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Eu(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	70%

2Nd(3+)*3SO4(2-)*99H2O = Nd2(SO4)3*99H2O + 2-phenethylhydrazine sulfate (156-51-4) → Nd(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Nd(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	68%

hydrated cerium(III) sulfate + 2-phenethylhydrazine sulfate (156-51-4) → Ce(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Ce(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	67%

2-phenethylhydrazine sulfate (156-51-4) + ethyl (ethoxymethylene)cyanoacetate (94-05-3) → ethyl 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylate (252903-25-6)

Conditions	Yield
Stage #1: 2-phenethylhydrazine sulfate With sodium ethanolate In ethanol at 20℃; for 1h; Inert atmosphere; Stage #2: ethyl (ethoxymethylene)cyanoacetate In ethanol at 0 - 70℃; for 14.5h; Inert atmosphere; regioselective reaction;	67%

lanthanum(III) sulphate hydrate + 2-phenethylhydrazine sulfate (156-51-4) → La(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [La(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	63%

2Pr(3+)*3SO4(2-)*99H2O = Pr2(SO4)3*99H2O + 2-phenethylhydrazine sulfate (156-51-4) → Pr(3+)*2SO4(2-)*2H2O*C6H5CH2CH2NH2NH2(1+) = [Pr(SO4)2(H2O)2(C6H5CH2CH2NH2NH2)]

Conditions	Yield
In sulfuric acid aq. H2SO4; (aerobic conditions); addn. of the org. salt to a hot filtered soln. of the metal sulfate in aq. H2SO4, stirring (50-60°C, 30 min); storage (room temp., overnight), filtration, washing (H2O; EtOH; Et2O), drying (vac., P4O10); elem. anal.;	61%

(S)-N-[2-oxo-3-(5-oxo-2,3,4,5-tetrahydro-benzo[b]oxepin-8-yl)-oxazolidin-5-ylmethyl]-acetamide (740842-28-8) + 2-phenethylhydrazine sulfate (156-51-4) → (S)-N-[3-(2-phenethyl-4,5-dihydro-2H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide + (S)-N-[3-(1-phenethyl-4,5-dihydro-1H-6-oxa-1,2-diaza-benzo[e]azulen-8-yl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide

Conditions	Yield
With triethylamine In ethanol at 20℃; for 20h;

2-phenethylhydrazine sulfate (156-51-4) → benzaldehyde (2-phenylethyl)hydrazone

Conditions	Yield
With sodium hydroxide; benzaldehyde In ethanol

(E)-2(R)-[1(S)-(tert.-butoxycarboxycarbonyl)-4-phenyl-3-butenyl]-4-methylvaleric acid + 2-phenethylhydrazine sulfate (156-51-4) → (E)-2(R)-[1(S)-(tert-butoxy-carbonyl)-4-phenyl-3-butenyl]-4-methyl-2'-(2-phenylethyl)valerohydrazide (253795-02-7)

C20H29N3O3 + 2-phenethylhydrazine sulfate (156-51-4) → C26H32N4O2 (1092481-46-3) + C26H32N4O2 (1092481-47-4)

Conditions	Yield
Stage #1: 2-phenethylhydrazine sulfate With ethanol; sodium at 20℃; for 0.333333h; Stage #2: C20H29N3O3 In ethanol at 85℃; for 144h; Product distribution / selectivity;

p-fluorobenzoylacetone (29681-98-9) + 2-phenethylhydrazine sulfate (156-51-4) → 5-(4-fluorophenyl)-3-methyl-1-(2-phenylethyl)-1H-pyrazole (1221503-87-2)

Conditions	Yield
With triethylamine; trifluoroacetic acid In isopropyl alcohol at 80℃; for 2h;

5-bromo-3-bromo-3H-isobenzofuran-1-one (102126-70-5) + 2-phenethylhydrazine sulfate (156-51-4) → 6-bromo-2-phenethyl-1-phthalazinone (1251402-12-6)

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 20℃;

2-phenethylhydrazine sulfate (156-51-4) → methyl 2-(2-carbamothioyl-2-phenethylhydrazinyl)-2-oxoacetate (1562528-42-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 50 h / 78 °C 2: tetrahydrofuran / 14 h / 20 °C View Scheme

2-phenethylhydrazine sulfate (156-51-4) → 6-hydroxy-2-phenethyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (1562528-36-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / 50 h / 78 °C 2: tetrahydrofuran / 14 h / 20 °C 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 14.5 h / 20 - 50 °C View Scheme

Downstream Products

• 61781-16-6 C₁₅H₂₃N₃OS 
• 253795-02-7 (E)-2(R)-[1(S)-(tert-butoxy-carbonyl)-4-phenyl-3-butenyl]-4-methyl-2'-(2-phenylethyl)valerohydrazide 
• 252903-25-6 ethyl 5-amino-1-(2-phenylethyl)-1H-pyrazole-4-carboxylate 
• 3473-12-9 1-phenethylhydrazinecarbothioamide 
• 1562528-36-2 6-hydroxy-2-phenethyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one 
• 1562528-42-0 methyl 2-(2-carbamothioyl-2-phenethylhydrazinyl)-2-oxoacetate 
• 1316122-43-6 2-phenethyl-5-pyridin-2-yl-2H-pyrazol-3-ylamine 
• 1251402-12-6 6-bromo-2-phenethyl-1-phthalazinone 
• 1221503-87-2 5-(4-fluorophenyl)-3-methyl-1-(2-phenylethyl)-1H-pyrazole 
• 1092481-46-3 C₂₆H₃₂N₄O₂ 
• 1092481-47-4 C₂₆H₃₂N₄O₂