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

Chemical Properties

A white powder or pearly platelets.

Originator

Nardil ,Parke Davis, US ,1959

Uses

Different sources of media describe the Uses of 156-51-4 differently. You can refer to the following data:
1. antihistaminic
2. Phenelzine Sulfate is a hydrazine derivative that is a non-selective and irreversible monoamine oxidase inhibitor (MAOI) and also inhibits GABA-transaminase (GABA-T), markedly increasing brain GABA levels. It is an antidep ressant and anxiolytic used in the treatment of major depressive disorder (MDD) as well as other neural disorders.

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.

Brand name

Nardil (Parke-Davis).

Therapeutic Function

Psychostimulant

General Description

Phenelzine sulfate, 2-(phenylethyl)hydrazine sulfate(Nardil), is an effective antidepressant agent. A mechanismbasedinactivator, it irreversibly inactivates the enzyme orits cofactor, presumably after oxidation to the diazine,which can then break up into molecular nitrogen, a hydrogen atom, and a phenethyl free radical. The latter would bethe active species in irreversible inhibition.

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 
• 92487-09-7 N-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-N'-phenethyl-hydrazine; compound with sulfuric acid 
• 92487-11-1 1-[3-(Phenethyl-hydrazonomethyl)-indol-1-yl]-ethanone; compound with sulfuric acid 
• 60-12-8 2-phenylethanol 
• 144464-30-2 1-Nitroso-1-(2-phenylethyl)-hydrazin 
• 222162-23-4 3-(5-carboxy-furan-2-yl)indazole 
• 253795-02-7 (E)-2(R)-[1(S)-(tert-butoxy-carbonyl)-4-phenyl-3-butenyl]-4-methyl-2'-(2-phenylethyl)valerohydrazide 
• 1092481-46-3 C₂₆H₃₂N₄O₂ 
• 1092481-47-4 C₂₆H₃₂N₄O₂ 
• 1221503-87-2 5-(4-fluorophenyl)-3-methyl-1-(2-phenylethyl)-1H-pyrazole 
• 1251402-12-6 6-bromo-2-phenethyl-1-phthalazinone