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Pyrrolidine dithiocarbamate

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Pyrrolidine dithiocarbamate
Names
IUPAC name Pyrrolidine-1-carbodithioic acid
Other names Pyrrolidinedithiocarbamate; 1-Pyrrolidinecarbodithioic acid; Pyrrolidine dithiocarbamic acid
Identifiers
CAS Number
3D model (JSmol)
Abbreviations PDTC
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8)Key: VSWDORGPIHIGNW-UHFFFAOYSA-N
  • InChI=1/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8)Key: VSWDORGPIHIGNW-UHFFFAOYAF
SMILES
  • C1CCN(C1)C(=S)S
Properties
Chemical formula C5H9NS2
Molar mass 147.25 g·mol
Density 1.264 g/cm
Boiling point 199.7 °C (391.5 °F; 472.8 K) at 760 mm Hg
Hazards
Flash point 74.6 °C (166.3 °F; 347.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Pyrrolidine dithiocarbamate (PDTC) are a family of closely related drugs used for a metal chelation, induction of G1 phase cell cycle arrest, and preventing induction of nitric oxide synthase.

Pyrrolidine dithiocarbamate binds zinc such that the resulting complex can enter the cell and inhibit viral RNA-dependent RNA polymerase.

Reactions

Pyrrolidine dithiocarbamate, like other dithiocarbamates, forms coordination complexes with a variety of transition metals. One example is Fe(S2CNC4H8)3.

See also

References

  1. Moon, Sung-Kwon; Jung, Sun-Young; Choi, Yung-Hyun; Lee, Young-Choon; Patterson, Cam; Kim, Cheorl-Ho (2004). "PDTC, metal chelating compound, induces G1 phase cell cycle arrest in vascular smooth muscle cells through inducing p21 expression: Involvement of p38 mitogen activated protein kinase". Journal of Cellular Physiology. 198 (2): 310–23. doi:10.1002/jcp.10728. PMID 14603533.
  2. Ammonium pyrrolidinedithiocarbamate at Sigma-Aldrich
  3. Lanke, K.; Krenn, B. M.; Melchers, W. J. G.; Seipelt, J.; van Kuppeveld, F. J. M. (1 April 2007). "PDTC inhibits picornavirus polyprotein processing and RNA replication by transporting zinc ions into cells". Journal of General Virology. 88 (4): 1206–1217. doi:10.1099/vir.0.82634-0.
  4. Martin, R. L.; Rohde, N. M.; Robertson, G. B.; Taylor, D. (1974). "Structural Characterization of Tris(pyrrolidyldithiocarbamato)iron(IV) Perchlorate. Iron Sulfide (FeS6) Complex of Unusually High Oxidation State". Journal of the American Chemical Society. 96 (11): 3647–3649. doi:10.1021/ja00818a048.
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