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P8765

Sigma-Aldrich

Ammonium pyrrolidinedithiocarbamate

~99%

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Synonym(s):
1-Pyrrolidinecarbodithioic acid ammonium salt, APDC, Ammonium pyrrolidinecarbodithioate, PDC, PDTC
Linear Formula:
C5H9NS2 · NH3
CAS Number:
Molecular Weight:
164.29
Beilstein:
3730472
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

microbial

Quality Level

Assay

~99%

form

(powderor powder with lumps)

mp

153-155 °C (lit.)

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

storage temp.

2-8°C

SMILES string

N.SC(=S)N1CCCC1

InChI

1S/C5H9NS2.H3N/c7-5(8)6-3-1-2-4-6;/h1-4H2,(H,7,8);1H3

InChI key

MDDIUTVUBYEEEM-UHFFFAOYSA-N

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General description

Ammonium pyrrolidinedithiocarbamate is a nuclear factor κB (NF-κB) inhibitor. It functions as a chelating agent, which allows the preconcentration of trace metals from solution. Pyrrolidinedithiocarbamate (PDTC) has antioxidant properties. It inhibits apoptosis in lymphocytes, neurons and vascular endothelial cells.

Application

Ammonium pyrrolidinedithiocarbamate has been used:
  • to inhibit nuclear factor κB (NF-κB) mobilization and TNF (tumor necrosis factor) production in human monocytes
  • to reduce neutrophil activity in rats
  • to prevent Ca2+ influx in adriamycin (ADR)-treated podocytes

to abrogate the microRNA-146a promoter luciferase reporter activity in human brain cells

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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  1. How does the storage temperature relate to shipping conditions?

    The storage conditions that a Sigma-Aldrich catalog and label recommend for products are deliberately conservative. For many products, long-term storage at low temperatures will increase the time during which they are expected to remain in specification and therefore are labeled accordingly. Where short-term storage, shipping time frame, or exposure to conditions other than those recommended for long-term storage will not affect product quality, Sigma-Aldrich will ship at ambient temperature. The products sensitive to short-term exposure to conditions other than their recommended long-term storage are shipped on wet or dry ice. Ambient temperature shipping helps to control shipping costs for our customers. At any time, our customers can request wet- or dry-ice shipment, but the special handling is at customer expense if our product history indicates that the product is stable for regular shipment. See Shipping and Storage for more information.

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  6. How can I prepare a solution of Product P8765, Ammonium pyrrolidinedithiocarbamate?

    Ammonium pyrrolidinedithiocarbamate is soluble in water at a concentration of approximately 50 mg/mL.

  7. What is the solution stability of Product P8765, Ammonium pyrrolidinedithiocarbamate?

    Sigma-Aldrich has not performed a controlled solution stability test on PDTC. However, we have found that aqueous stock solutions are typically stable for at least one month when stored at -20 °C.

  8. What are some functions reported for Product P8765, Ammonium pyrrolidinedithiocarbamate?

    PDTC has been reported to repress vascular cell adhesion molecule-1 (VCAM-1) activation by Interleukin-1β in cultured human umbilical vein endothelial calls. Marui, M., et al., J. Clin. Invest, 92, 1866 (1993).  It inhibits the induction of nitric oxide synthase activity in rat alveolar macrophages. Sherman, M.P., et al., Biochem. Biophys. Res. Commun. 191, 1301-1308 (1993).  It is an Inhibitor of nuclear factor kappa B., Eberhardt, et al. Biochem. Biophys. Res. Commun. 200, 163 (1994). PDTC at 100  μM, totally inhibited the NF-kappa B response in intact cells. Schreck, R., et al., J. Exp. Med. 175 , 1181-1194 (1992). It activates cAMP-dependent protein kinase (PKA) in a colorectal cancer cell line. Chinery, R., et al., J. Biol. Chem., 272, 30356 - 30361, (1997).

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Induction of apoptosis by pyrrolidinedithiocarbamate and N-acetylcysteine in vascular smooth muscle cells
Tsai JC, et al.
The Journal of Biological Chemistry, 271(7), 3667-3670 (1996)
Multi-element preconcentration of heavy metal ions from aqueous solution by APDC impregnated activated carbon
Daorattanachai P, et al.
Talanta, 67(1), 59-64 (2005)
An NF-kappaB-sensitive micro RNA-146a-mediated inflammatory circuit in Alzheimer disease and in stressed human brain cells
Lukiw WJ, et al.
The Journal of Biological Chemistry, 283(46), 31315-31322 (2008)
Quan Zhou et al.
Oncogene, 39(7), 1414-1428 (2019-10-30)
Gastric cancer (GC) is characterized by extensive local invasion, distant metastasis and poor prognosis. In most cases, GC progression is associated with aberrant expression of cytokines or activation of signaling cascades mediated by tumor-stroma interactions. However, the mechanisms by which
Reduction of neutrophil activity decreases early microvascular injury after subarachnoid haemorrhage
Friedrich V, et al.
Journal of Neuroinflammation, 8(1), 103-103 (2011)

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