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5108-96-3

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5108-96-3 Usage

Description

Ammonium 1-pyrrolidinedithiocarbamate, also known as Ammonium pyrrolidinedithiocarbamate (APDC), is a metal chelating compound with potent and reversible inhibition of nuclear factor κB (NF-κB) activation. It exhibits antioxidant properties and is effective in inhibiting apoptosis in various cell types, including lymphocytes, neurons, and vascular endothelial cells. APDC is characterized by its pale yellow crystalline solid appearance.

Uses

Ammonium 1-pyrrolidinedithiocarbamate is used as a chelating agent for the preconcentration of trace metals from solution due to its ability to bind with metal ions.
Used in Pharmaceutical Applications:
Ammonium 1-pyrrolidinedithiocarbamate is used as an NF-κB inhibitor for its various therapeutic applications, including:
1. Inhibiting NF-κB mobilization and TNF (tumor necrosis factor) production in human monocytes, which can be beneficial in treating inflammatory conditions.
2. Reducing neutrophil activity in rats, which may help in managing inflammatory responses.
3. Preventing Ca2+ influx in adriamycin (ADR)-treated podocytes, potentially aiding in the treatment of kidney-related diseases.
4. Abolishing the microRNA-146a promoter luciferase reporter activity in human brain cells, which could have implications in neurological disorders.
Used in Cellular Research:
Ammonium 1-pyrrolidinedithiocarbamate is used as a tool in cellular research to:
1. Induce apoptosis in rat smooth muscle cells, which can provide insights into cell death mechanisms.
2. Inhibit apoptosis in leukemia HL-60 cells, offering potential applications in cancer research and treatment.
3. Prevent the induction of nitric oxide synthetase by inhibiting the translation of NOS mRNA, which may have implications in understanding and treating various diseases associated with nitric oxide dysregulation.

Biochem/physiol Actions

Prevents induction of nitric oxide synthetase by inhibiting translation of NOS mRNA; induces apoptosis in rat smooth muscle cells and inhibits apoptosis in leukemia HL-60 cells.

Purification Methods

Purify the salt by recrystallising twice by dissolving in MeOH and adding Et2O. It has also been purified by recrystallisation from EtOH. It is used for the precipitation of As, Bi, Cd, Co, Cu, Fe, Mn, Ni, Pb, Sb, Su, V and Zn from acidic solutions [Kinrade & van Loon Anal Chem 46 1894 1974]. The ethyl ester has b 87-89o/0.01mm. [Synthesis and Polarography: Kitagawa & Taku Bull Chem Soc Jpn 64 2151 1973, Malissa & Sch.ffmann Mikrochim Acta 187 1955, Beilstein 20 III/IV 195, 20/1 V 331.]

Check Digit Verification of cas no

The CAS Registry Mumber 5108-96-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,1,0 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 5108-96:
(6*5)+(5*1)+(4*0)+(3*8)+(2*9)+(1*6)=83
83 % 10 = 3
So 5108-96-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H9N.CH3NS2.H3N/c1-2-4-5-3-1;2-1(3)4;/h5H,1-4H2;(H3,2,3,4);1H3

5108-96-3 Well-known Company Product Price

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  • Alfa Aesar

  • (B23731)  1-Pyrrolidinecarbodithioic acid ammonium salt, 98%   

  • 5108-96-3

  • 25g

  • 581.0CNY

  • Detail
  • Alfa Aesar

  • (B23731)  1-Pyrrolidinecarbodithioic acid ammonium salt, 98%   

  • 5108-96-3

  • 100g

  • 1377.0CNY

  • Detail
  • Sigma-Aldrich

  • (09935)  Ammoniumpyrrolidinedithiocarbamate  purum p.a., ≥98.0% (NT)

  • 5108-96-3

  • 09935-25G

  • 513.63CNY

  • Detail
  • Sigma-Aldrich

  • (09935)  Ammoniumpyrrolidinedithiocarbamate  purum p.a., ≥98.0% (NT)

  • 5108-96-3

  • 09935-100G

  • 1,705.86CNY

  • Detail
  • Sigma-Aldrich

  • (09935)  Ammoniumpyrrolidinedithiocarbamate  purum p.a., ≥98.0% (NT)

  • 5108-96-3

  • 09935-1KG

  • 12,706.20CNY

  • Detail

5108-96-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Ammonium 1-pyrrolidinedithiocarbamate

1.2 Other means of identification

Product number -
Other names Ammonium pyrrolidine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5108-96-3 SDS

5108-96-3Synthetic route

pyrrolidine
123-75-1

pyrrolidine

carbon disulfide
75-15-0

carbon disulfide

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

Conditions
ConditionsYield
With ammonium hydroxide In diethyl ether for 1h;85%
With ammonium hydroxide In ethanol
With ammonia
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

(benzoylaminomethyl)triethylammonium chloride
78134-74-4

(benzoylaminomethyl)triethylammonium chloride

benzamidomethyl pyrroldinedithiocarbamate

benzamidomethyl pyrroldinedithiocarbamate

Conditions
ConditionsYield
With triethylamine In water at 20℃; for 1h;95.7%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

methyl 4-(2-bromoacetyl)benzoate
56893-25-5

methyl 4-(2-bromoacetyl)benzoate

methyl 4-(2-((pyrrolidine-1-carbonothioyl)thio)acetyl)benzoate
1593781-46-4

methyl 4-(2-((pyrrolidine-1-carbonothioyl)thio)acetyl)benzoate

Conditions
ConditionsYield
In acetone at 20℃; for 8h;90.1%
In acetone at 20℃; for 8h;90.1%
In acetone at 20℃; for 1.5h;83%
potassium tetrabromoaurate(III) dihydrate

potassium tetrabromoaurate(III) dihydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

dibromido[N-dithiocarboxy-kS,kS’-pyrrolidine]gold(III)

dibromido[N-dithiocarboxy-kS,kS’-pyrrolidine]gold(III)

Conditions
ConditionsYield
In water at 20℃; for 0.166667h;89.6%
(1,3-diisopropylimidazolin-2-ylidene)gold(I) chloride

(1,3-diisopropylimidazolin-2-ylidene)gold(I) chloride

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Au(N,N’-niPr2NHC)(pyrrolidinedithiocarbamate)]

[Au(N,N’-niPr2NHC)(pyrrolidinedithiocarbamate)]

Conditions
ConditionsYield
In ethanol at 24.84℃; for 6h;89%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

p-nitrobenzyl 3-<(3-mesyloxypropyl)thio>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
77597-29-6

p-nitrobenzyl 3-<(3-mesyloxypropyl)thio>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

p-nitrobenzyl 3-<<3-<(1-pyrrolidinylcarbothioyl)thio>propyl>thio>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
77597-31-0

p-nitrobenzyl 3-<<3-<(1-pyrrolidinylcarbothioyl)thio>propyl>thio>-7-oxo-4-thia-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Conditions
ConditionsYield
In dimethyl sulfoxide for 1h; Ambient temperature;88%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[(dppe)Pt(κ(2)S,S-S2CNC4H8)]Cl

[(dppe)Pt(κ(2)S,S-S2CNC4H8)]Cl

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;88%
(N,N'-diethylbenzimidazolin-2-ylidene)gold(I) chloride

(N,N'-diethylbenzimidazolin-2-ylidene)gold(I) chloride

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Au(N,N’-niEt2benzimidazole)(pyrrolidinedithiocarbamate)]

[Au(N,N’-niEt2benzimidazole)(pyrrolidinedithiocarbamate)]

Conditions
ConditionsYield
In ethanol at 24.84℃; for 6h;88%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

C19H18ClN3O2Pt

C19H18ClN3O2Pt

C22H23N3O2PtS2

C22H23N3O2PtS2

Conditions
ConditionsYield
Stage #1: C19H18ClN3O2Pt With silver(I) hexafluorophosphate In 2-methoxy-ethanol for 5h; Darkness;
Stage #2: ammonium tetramethylenedithiocarbamate With acetonitrile for 0.5h; Further stages;
87.9%
1,10-phenanthroline-5-amine
54258-41-2

1,10-phenanthroline-5-amine

europium(III) chloride hexahydrate

europium(III) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

C27H33EuN6S6

C27H33EuN6S6

Conditions
ConditionsYield
In methanol at 20℃; for 0.166667h;86.5%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

bis(tetramethylenedithiocarbamato) Ni(II) complex
30117-29-4

bis(tetramethylenedithiocarbamato) Ni(II) complex

Conditions
ConditionsYield
In water at 20℃; for 1h;86%
potassium tetrachloroaurate(III) dihydrate

potassium tetrachloroaurate(III) dihydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

dichlorido[N-dithiocarboxy-kS,kS’-pyrrolidine]gold(III)

dichlorido[N-dithiocarboxy-kS,kS’-pyrrolidine]gold(III)

Conditions
ConditionsYield
In water at 20℃; for 0.166667h;85.3%
potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Pd(κ2-pyrrolidine dithiocarbamate)2]
41060-78-0

[Pd(κ2-pyrrolidine dithiocarbamate)2]

Conditions
ConditionsYield
In water at 20℃; for 1h;83%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

2-chloro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide
21521-87-9

2-chloro-N-(5-methyl-1,3,4-thiadiazol-2-yl)acetamide

S-(2-acetylamino-5-methyl 1,3,4-thiadiazolyl)-N-pyrrolidino dithiocarbamate

S-(2-acetylamino-5-methyl 1,3,4-thiadiazolyl)-N-pyrrolidino dithiocarbamate

Conditions
ConditionsYield
In water; acetone for 3h; Ambient temperature;82%
cis-dichlorobis(triphenylphosphine)platinum(II)
10199-34-5, 14056-88-3, 15604-36-1

cis-dichlorobis(triphenylphosphine)platinum(II)

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

(PPh3)Pt(κS,S2CNC4H8)-(κ(2)S,S-S2CNC4H8)
1449578-51-1

(PPh3)Pt(κS,S2CNC4H8)-(κ(2)S,S-S2CNC4H8)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 48h; Inert atmosphere;81%
cobalt(II) chloride hexahydrate

cobalt(II) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Co(κ2-pyrrolidine dithiocarbamate)2]
54854-44-3

[Co(κ2-pyrrolidine dithiocarbamate)2]

Conditions
ConditionsYield
In water at 20℃; for 1h;81%
dibromobis(triphenylphosphine)nickel(II)
36673-36-6, 111408-20-9, 14126-37-5, 54053-52-0

dibromobis(triphenylphosphine)nickel(II)

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

(PPh3)Ni(Br)(κ2S,S-S2CNC4H8)

(PPh3)Ni(Br)(κ2S,S-S2CNC4H8)

Conditions
ConditionsYield
for 18h; Inert atmosphere; Schlenk technique;80%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

neodymium(III) chloride hexahydrate

neodymium(III) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Nd(pyrrolidinedithiocarbamato)3(1,10-phenanthroline)]
845886-55-7

[Nd(pyrrolidinedithiocarbamato)3(1,10-phenanthroline)]

Conditions
ConditionsYield
Stage #1: neodymium(III) chloride hexahydrate; ammonium tetramethylenedithiocarbamate In methanol
Stage #2: 1,10-Phenanthroline In methanol for 1h;
78.5%
C15H24Au2Br2N4

C15H24Au2Br2N4

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Au2(μ2-N-nBu-NHC-CH2-NHC-N-nBu)(pyrrolidinedithiocarbamate)](Br)

[Au2(μ2-N-nBu-NHC-CH2-NHC-N-nBu)(pyrrolidinedithiocarbamate)](Br)

Conditions
ConditionsYield
In ethanol at 24.84℃; for 6h;78%
copper(II) chloride hexahydrate

copper(II) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Cu(κ2-pyrrolidine dithiocarbamate)2]
23301-60-2

[Cu(κ2-pyrrolidine dithiocarbamate)2]

Conditions
ConditionsYield
In water at 20℃; for 1h;78%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[Pt(κ2-pyrrolidine dithiocarbamate)2]
41060-59-7

[Pt(κ2-pyrrolidine dithiocarbamate)2]

Conditions
ConditionsYield
In water at 20℃; for 1h;77%
bis(triphenylphosphine)palladium(II) chloride
15604-37-2, 13965-03-2, 28966-81-6

bis(triphenylphosphine)palladium(II) chloride

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

(PPh3)Pd(Cl)(κ(2)S,S-S2CNC4H8)
1449578-49-7

(PPh3)Pd(Cl)(κ(2)S,S-S2CNC4H8)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;75%
(1,2-bis(diphenylphosphino)ethane)palladium(II) chloride
19978-61-1

(1,2-bis(diphenylphosphino)ethane)palladium(II) chloride

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

[(dppe)Pd(κ(2)S,S-S2CNC4H8)]Cl

[(dppe)Pd(κ(2)S,S-S2CNC4H8)]Cl

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;75%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

copper dichloride

copper dichloride

bis(pyrrolidinedithiocarbamato)Cu(II)

bis(pyrrolidinedithiocarbamato)Cu(II)

Conditions
ConditionsYield
In methanol for 0.25h;74%
sodium molybdate

sodium molybdate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

(pyrrolidyldithiocarbamato)dioxomolybdenum(VI)
21881-93-6

(pyrrolidyldithiocarbamato)dioxomolybdenum(VI)

Conditions
ConditionsYield
With hydrogenchloride In water for 2h;72%
With hydrogenchloride In water for 2h;72%
1-naphthyltellurium(IV) trichloride
36062-78-9

1-naphthyltellurium(IV) trichloride

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

NaphTe(dtcpyr)
1175542-85-4

NaphTe(dtcpyr)

Conditions
ConditionsYield
In tetrahydrofuran for 0.166667h;71%
ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

2-chloro-N-(6,8-dibromo-2-methyl-4-oxo-quinazolin-3(4H)-yl)-acetamide
94650-28-9

2-chloro-N-(6,8-dibromo-2-methyl-4-oxo-quinazolin-3(4H)-yl)-acetamide

Pyrrolidine-1-carbodithioic acid (6,8-dibromo-2-methyl-4-oxo-4H-quinazolin-3-ylcarbamoyl)-methyl ester
100805-78-5

Pyrrolidine-1-carbodithioic acid (6,8-dibromo-2-methyl-4-oxo-4H-quinazolin-3-ylcarbamoyl)-methyl ester

Conditions
ConditionsYield
In acetone 1a) room temp., 30 min, 1b) reflux, 1.5 h;70%
D-Glucose
2280-44-6

D-Glucose

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

β-D-glucopyranosyl 1-pyrrolidinecarbodithioate

β-D-glucopyranosyl 1-pyrrolidinecarbodithioate

Conditions
ConditionsYield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In water; acetonitrile at -15℃; for 1h; stereoselective reaction;70%
1,10-Phenanthroline
66-71-7

1,10-Phenanthroline

europium(III) chloride hexahydrate

europium(III) chloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

Eu(III)((1,10-phenanthroline)(pyrrolidinedithiocarbamate)3
866957-38-2

Eu(III)((1,10-phenanthroline)(pyrrolidinedithiocarbamate)3

Conditions
ConditionsYield
Stage #1: europium(III) chloride hexahydrate; ammonium tetramethylenedithiocarbamate In methanol
Stage #2: 1,10-Phenanthroline In methanol for 1h;
70%
1,10-phenanthroline-5-amine
54258-41-2

1,10-phenanthroline-5-amine

lanthanum(III) trichloride hexahydrate

lanthanum(III) trichloride hexahydrate

ammonium tetramethylenedithiocarbamate
5108-96-3

ammonium tetramethylenedithiocarbamate

C27H33LaN6S6

C27H33LaN6S6

Conditions
ConditionsYield
In methanol at 20℃; for 0.166667h;70%

5108-96-3Relevant articles and documents

Tin(IV) complexes of pyrrolidinedithiocarbamate: Synthesis, characterisation and antifungal activity

Menezes,Vieira,De Lima,Porto,Cortes,Ardisson,Albrecht-Schmitt

, p. 1277 - 1282 (2005)

The reaction of ammonium pyrrolidinedithiocarbamate, [NH4{S 2CN(CH2)4}], with SnCl2, [Sn(C 6H5)2Cl2], [Sn(C6H 5)3Cl], [Sn(C4H9)2Cl 2] and [Sn(C6H11)3Cl] produced in good yield the compounds [Sn{S2CN(CH2)4} 2Cl2] (1), [Sn{S2CN(CH2) 4}2Ph2] (2), [Sn{S2CN(CH 2)4}Ph3] (3), [Sn{S2CN(CH 2)4}2n-Bu2] (4) and [Sn{S 2CN(CH2)4}Cy3] (5). The complexes were characterised by infrared, multinuclear NMR (1H, 13C{1H} and 119Sn{1H}) and 119Sn Moessbauer spectroscopies. In addition, the crystal structure of 4 was determined by X-ray crystallography. The in vitro antifungal activity of the tin(IV) complexes as well of the ligand was performed on human pathogenic fungi, Candida albicans, in concentrations of 0.025; 0.050; 0.100; 0.200; 0.400; 0.800; 1.600 and 3.200:mM. The microorganism presented resistance to the dithiocarbamate ligand and all tin(IV) complexes tested were actives. The highest activity was found for compounds 1 and 4.

SYNTHESIS OF AND STUDIES ON IRON(III) MONOTHIO- AND DITHIOCARBAMATES COMPLEXES

Wajda, Stanislaw,Piotrowska, Alina,Szmaj, Marianna,Zarzeczny, Augustyn

, p. 395 - 404 (2007/10/02)

Iron(III) monothio- and dithiocarbamates complexes, Fe(mtc)3, Fe(dtc)3 and Fe(dtc)2X have been synthesized and their Moessbauer, IR and electronic spectroscopy and magnetic measurements have been carried out. complexes show anomalous magnetic behavior arising from 2T (low spin, S=1/26A (high spin, S=5/2) spin-equilibrium.The differences in ΔEQ values have been explained by distortions from D3 symmetry, due to the asymmetry of FeS3O3 core.

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