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{{Chembox
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 312823060
| verifiedrevid = 437572586
| ImageFile = Pyrrolidine dithiocarbamate.png
| ImageFile = Pyrrolidinedithiocarbamate.png
| ImageSize = 150px
| ImageSize = 150px
| IUPACName = Pyrrolidine-1-carbodithioic acid
| IUPACName = Pyrrolidine-1-carbodithioic acid
| OtherNames = Pyrrolidinedithiocarbamate; 1-Pyrrolidinecarbodithioic acid; Pyrrolidine dithiocarbamic acid
| OtherNames = Pyrrolidinedithiocarbamate; 1-Pyrrolidinecarbodithioic acid; Pyrrolidine dithiocarbamic acid
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| Abbreviations= PDTC
| Abbreviations = PDTC
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 25769-03-3
| CASNo = 25769-03-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RG3HRQ45HY
| PubChem = 65351
| PubChem = 65351
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| SMILES = S=C(S)N1CCCC1
| ChEBI = 78782
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 58828
⚫
| SMILES = C1CCN(C1)C(=S)S
| InChI = 1/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8)
| InChIKey = VSWDORGPIHIGNW-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H9NS2/c7-5(8)6-3-1-2-4-6/h1-4H2,(H,7,8)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = VSWDORGPIHIGNW-UHFFFAOYSA-N

}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=5|H=9|N=1|S=2
| C=5 | H=9 | N=1 | S=2
| Appearance =
| Appearance =
| Density = 1.264 g/cm<sup>3</sup>
| Density = 1.264 g/cm<sup>3</sup>
| MeltingPt =
| MeltingPt =
| BoilingPt = 199.7 °C @ 760mmHg
| BoilingPtC = 199.7
| BoilingPt_notes = at 760&nbsp;mm&nbsp;Hg
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt = 74.6 °C
| FlashPtC = 74.6
| Autoignition = }}
| AutoignitionPtC =
}}
}}
}}


'''Pyrrolidine dithiocarbamate''' (PDTC) is a [[chemical compound]] with the molecular formula C<sub>5</sub>H<sub>9</sub>NS<sub>2</sub>. PDTC and its [[salt (chemistry)|salts]], such as ammonium pyrrolidinecarbodithioate, are used for a variety of biochemical applications including metal [[chelation]], induction of G1 phase cell cycle arrest,<ref>{{cite journal | doi = 10.1002/jcp.10728 | pmid = 14603533 | year = 2004 | month = Feb | last1 = Moon | first1 = SK | last2 = Jung | first2 = SY | last3 = Choi | first3 = YH | last4 = Lee | first4 = YC | last5 = Patterson | first5 = C | last6 = Kim | first6 = CH | title = 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 | volume = 198 | issue = 2 | pages = 310–23 | issn = 0021-9541 | journal = Journal of cellular physiology }}</ref> and preventing induction of [[nitric oxide synthase]].<ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=P8765|SIGMA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Ammonium pyrrolidinedithiocarbamate] at [[Sigma-Aldrich]]</ref>
'''Pyrrolidine dithiocarbamate''' (PDTC) are a family of closely related drugs used for a metal [[chelation]], induction of G1 phase cell cycle arrest,<ref>{{cite journal |doi=10.1002/jcp.10728 |pmid=14603533 |title=PDTC, metal chelating compound, induces G1 phase cell cycle arrest in vascular smooth muscle cells through inducing p21<sup>Cip1</sup> expression: Involvement of p38 mitogen activated protein kinase |journal=Journal of Cellular Physiology |volume=198 |issue=2 |pages=310–23 |year=2004 |last1=Moon |first1=Sung-Kwon |last2=Jung |first2=Sun-Young |last3=Choi |first3=Yung-Hyun |last4=Lee |first4=Young-Choon |last5=Patterson |first5=Cam |last6=Kim |first6=Cheorl-Ho }}</ref> and preventing induction of [[nitric oxide synthase]].<ref>[http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=P8765|SIGMA&N5=SEARCH_CONCAT_PNO|BRAND_KEY&F=SPEC Ammonium pyrrolidinedithiocarbamate] at [[Sigma-Aldrich]]</ref>

Pyrrolidine dithiocarbamate binds zinc such that the resulting complex can enter the cell and inhibit viral [[RNA-dependent RNA polymerase]].<ref>{{cite journal |last1=Lanke |first1=K. |last2=Krenn |first2=B. M. |last3=Melchers |first3=W. J. G. |last4=Seipelt |first4=J. |last5=van Kuppeveld |first5=F. J. M. |title=PDTC inhibits picornavirus polyprotein processing and RNA replication by transporting zinc ions into cells |journal=Journal of General Virology |date=1 April 2007 |volume=88 |issue=4 |pages=1206–1217 |doi=10.1099/vir.0.82634-0|doi-access=free }}</ref>

==Reactions==
Pyrrolidine dithiocarbamate, like other dithiocarbamates, forms [[coordination complex]]es with a variety of [[transition metal]]s. One example is {{chem2|Fe(S2CNC4H8)3}}.<ref>{{cite journal |doi=10.1021/ja00818a048|title=Structural Characterization of Tris(pyrrolidyldithiocarbamato)iron(IV) Perchlorate. Iron Sulfide (FeS<sub>6</sub>) Complex of Unusually High Oxidation State |year=1974 |last1=Martin |first1=R. L. |last2=Rohde |first2=N. M. |last3=Robertson |first3=G. B. |last4=Taylor |first4=D. |journal=Journal of the American Chemical Society |volume=96 |issue=11 |pages=3647–3649 }}</ref>

==See also==
* [[ionophore]]


==References==
==References==
{{reflist}}
{{reflist}}


[[Category:Pyrrolidines]]
[[Category:1-Pyrrolidinyl compounds]]
[[Category:Dithiocarbamates]]
[[Category:Dithiocarbamates]]
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