Pyrrolidine dithiocarbamate

Pyrrolidine dithiocarbamate
Names
	IUPAC name Pyrrolidine-1-carbodithioic acid
	Other names Pyrrolidinedithiocarbamate; 1-Pyrrolidinecarbodithioic acid; Pyrrolidine dithiocarbamic acid
Identifiers
CAS Number	25769-03-3 ;
3D model (JSmol)	Interactive image;
Abbreviations	PDTC
ChEBI	CHEBI:78782 ;
ChemSpider	58828 ;
PubChem CID	65351;
UNII	RG3HRQ45HY ;
CompTox Dashboard (EPA)	DTXSID00180437 ;
	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−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). verify (what is ?) 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]

References

^ 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^Cip1 expression: Involvement of p38 mitogen activated protein kinase". Journal of Cellular Physiology. 198 (2): 310–23. doi:10.1002/jcp.10728. PMID 14603533.
^ Ammonium pyrrolidinedithiocarbamate at Sigma-Aldrich
^ 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.
^ 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.

[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^Cip1 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.

[1]

[2]

[3]

[4]

Reactions

See also

References