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P8765

Sigma-Aldrich

Ammonium pyrrolidinedithiocarbamate

~99%

Synonym(s):

1-Pyrrolidinecarbodithioic acid ammonium salt, APDC, Ammonium pyrrolidinecarbodithioate, PDC, PDTC

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About This Item

Linear Formula:
C5H9NS2 · NH3
CAS Number:
5108-96-3
Molecular Weight:
164.29
Beilstein:
3730472
EC Number:
225-834-4
MDL number:
MFCD00012720
UNSPSC Code:
12352107
PubChem Substance ID:
24278658
NACRES:
NA.77

biological source

microbial

Quality Level

200

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

Gene Information

human ... NOS1(4842) , NOS2(4843) , NOS2B(201288) , NOS2C(645740) , NOS3(4846) , RELA(5970)

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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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.

  2. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  3. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  4. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  5. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  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).

  9. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
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)
Electron transport chain inhibitors induce microglia activation through enhancing mitochondrial reactive oxygen species production
Ye J, et al.
Experimental Cell Research, 340(2), 315-326 (2016)
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)
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)
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