Pyrrolidine dithiocarbamate
Names
IUPAC name
Pyrrolidine-1-carbodithioic acid
Other names
Pyrrolidinedithiocarbamate; 1-Pyrrolidinecarbodithioic acid; Pyrrolidine dithiocarbamic acid
Identifiers
3D model (JSmol)
Abbreviations PDTC
ChEBI
ChemSpider
UNII
  • InChI=1S/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8) ☒N
    Key: VSWDORGPIHIGNW-UHFFFAOYSA-N ☒N
  • InChI=1/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8)
    Key: VSWDORGPIHIGNW-UHFFFAOYAF
  • C1CCN(C1)C(=S)S
Properties
C5H9NS2
Molar mass 147.25 g·mol−1
Density 1.264 g/cm3
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 [77 °F], 100 kPa).
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Infobox references

Pyrrolidine dithiocarbamate (PDTC) are a family of closely related drugs used for a metal chelation, induction of G1 phase cell cycle arrest,[1] and preventing induction of nitric oxide synthase.[2]

Pyrrolidine dithiocarbamate binds zinc such that the resulting complex can enter the cell and inhibit viral RNA-dependent RNA polymerase.[3]

Reactions

Pyrrolidine dithiocarbamate, like other dithiocarbamates, forms coordination complexes with a variety of transition metals. One example is Fe(S2CNC4H8)3.[4]

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 p21Cip1 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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