Record Information
Version2.0
Creation Date2009-06-19 21:58:49 UTC
Update Date2014-12-24 20:23:57 UTC
Accession NumberT3D1465
Identification
Common NameZinc dimethyldithiocarbamate
ClassSmall Molecule
DescriptionZinc dimethyldithiocarbamate is a chemical compound of zinc. Zinc is a metallic element with the atomic number 30. It is found in nature most often as the mineral sphalerite. Though excess zinc in harmful, in smaller amounts it is an essential element for life, as it is a cofactor for over 300 enzymes and is found in just as many transcription factors. (4, 5)
Compound Type
  • Amine
  • Carbamate
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Pesticide
  • Synthetic Compound
  • Zinc Compound
Chemical Structure
Thumb
Synonyms
Synonym
(SP-4-1)-bis(dimethylcarbamodithioato-S,S')-zinc
(T-4)-bis (dimethyldithiocarbamate-S,S )zinc
(T-4)-bis(dimethylcarbamodithioato-S ,S')-zinc
(T-4)-bis(dimethylcarbamodithioato-S,S')-zinc
(T-4)-Bis(dimethyldithiocarbamato-S,S')zinc
(T-4)-Bis(dimethyldithiocarbamato-S,S')zinc (9CI)
Aaprotect
Aaprotent
Aavolex
Aazira
Accelerator l
Accelerator MZ powder
Aceto zded
Aceto ZDMD
Alcobam ZM
Amyl zimate
Ancazate me
Antene
Bis(dimethylcarbamodithiato-s,s')-zinc
Bis(dimethylcarbamodithioato-s,s')zinc
Bis(dimethyldithiocarbama to)zinc
Bis(dimethyldithiocarbamat)zinc
Bis(dimethyldithiocarbamato)zinc
Bis(n,n-dimetil-ditiocarbammato)di zinco
Bis-dimethyldithiocarbamate de zinc
Carbamic acid, dimethyldithio-, Z inc salt (2:1)
Carbamic acid, dimethyldithio-, zinc salt (2:1)
Carbamodithioic acid, dimethyl-, zinc salt
Carbazinc
Caswell No. 931
Ciram
Corona corozate
Corozate
Crittam
Crittan
Crorzate
Cuman
Cuman l
Cymate
Dimethylcarbamodithioic acid, zinc complex
Dimethylcarbamodithioic acid, zinc salt
Dimethyldithiocarbamate zinc salt
Dimethyldithiocarbamic acid zinc salt
Dimethyldithiocarbamic acid, zinc salt
Drupina 90
Eptac 1
Fuclasin
Fuclasin ultra
Fuclasin-ultra
Fuklasin
Fungostop
Hermat ZDM
Hexazir
Karbam white
Methasan
Methazate
Methyl cymate
Methyl zimate
Methyl zineb
Methyl ziram
Mexene
Mezene
Micosin F30
Milam
Milbam
Milban
Molurame
MYCR onil
Mycronil
Nocceler PZ
Octocure ZDM-50
Orchard brand ziram
Perkacit ZDMC
Pomarsol z forte
Pomarsol z-forte
Pomarsolz
Pomarzol z-forte
Prodaram
Ramedit
RCRA waste no. P205
Rhodiacid
Rodisan
Sabceler PZ
Soxinal PZ
Soxinol PZ
Thiuram e
Tricarbamix z
Trikagol
Triscabol
Tsimat
Tsiram
Tsiram(russian)
Ultra zinc DMC
USAF p-2
Vancide
Vancide MA-96
Vancide mz-96
Vulcacure
Vulcacure ZM
Vulkacit l
Vulkacite l
Weisstaub
Z-c spray
Z-c-spray
Zarlate
Zarlate;carbamodithioic acid
ZC
Zeralte
Zerlate
Zimate
Zimate, methyl
Zinc bis dimethyldithiocarbamate
Zinc bis(dimethyldithiocarbamate)
Zinc bis(dimethyldithiocarbamoyl) disulfide
Zinc bis(dimethyldithiocarbamoyl)disulfide
Zinc bis(dimethyldithiocarbamoyl)disulphide
Zinc bis(dimethylthiocarbamoyl) disulfide
Zinc bis(dimethylthiocarbamoyl)disulfide
Zinc dimethyl dithiocarbamate
Zinc dimethyldithiocarbamic acid
Zinc n,n-dimethyldithiocarbamate
Zincmate
Zink dimethyldithiocarbamate
Zink-bis(n,n-dimethyl-dithiocarbamaat)
Zink-bis(n,n-dimethyl-dithiocarbamat)
Zinkcarbamate
Ziradin
Ziram
Ziram F4
Ziram granuflo
Ziram technical
Ziram W7 6
Ziram W76
Zirame
Ziramvis
Zirasan
Zirasan 90
Zirberk
Zirberk thynylestradiol ram
Ziretec
Zirex 90
Zirex fungicide
Ziride
Zirthane
Zitox
Chemical FormulaC6H12N2S4Zn
Average Molecular Mass305.842 g/mol
Monoisotopic Mass303.917 g/mol
CAS Registry Number137-30-4
IUPAC Namebis[(dimethylcarbamothioyl)sulfanyl]zinc
Traditional Nameziram
SMILESCN(C)C(=S)S[Zn]SC(=S)N(C)C
InChI IdentifierInChI=1S/2C3H7NS2.Zn/c2*1-4(2)3(5)6;/h2*1-2H3,(H,5,6);/q;;+2/p-2
InChI KeyInChIKey=DUBNHZYBDBBJHD-UHFFFAOYSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic transition metal salts. These are organic salt compounds containing a transition metal atom in its ionic form.
KingdomOrganic compounds
Super ClassOrganic salts
ClassOrganic metal salts
Sub ClassOrganic transition metal salts
Direct ParentOrganic transition metal salts
Alternative Parents
Substituents
  • Organic transition metal salt
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite crystals.
Experimental Properties
PropertyValue
Melting Point250°C
Boiling PointNot Available
Solubility0.065 mg/mL at 25°C [GUNTHER,FA et al. (1968)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP1.86ALOGPS
logP1.74ChemAxon
logS-3.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.24 m³·mol⁻¹ChemAxon
Polarizability26.56 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139000000-e6dfbc43c92ba0245ebe2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9100000000-c9631804bff9f34036cb2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9750000000-18a89bf261bf4687dd262019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3119000000-93b3e9f8d240e91db6962019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uy0-9625000000-08c5f6307170a4d62ca72019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-7971000000-d0912a64c40ba4d2c93a2019-02-23View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0k9i-6539000000-4cf7031e44557fbc7ee32014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityAnaemia results from the excessive absorption of zinc suppressing copper and iron absorption, most likely through competitive binding of intestinal mucosal cells. Unbalanced levels of copper and zinc binding to Cu,Zn-superoxide dismutase has been linked to amyotrophic lateral sclerosis (ALS). Stomach acid dissolves metallic zinc to give corrosive zinc chloride, which can cause damage to the stomach lining. Metal fume fever is thought to be an immune response to inhaled zinc. (4, 5, 1)
MetabolismZinc can enter the body through the lungs, skin, and gastrointestinal tract. Intestinal absorption of zinc is controlled by zinc carrier protein CRIP. Zinc also binds to metallothioneins, which help prevent absorption of excess zinc. Zinc is widely distributed and found in all tissues and tissues fluids, concentrating in the liver, gastrointestinal tract, kidney, skin, lung, brain, heart, and pancreas. In the bloodstream zinc is found bound to carbonic anhydrase in erythrocytes, as well as bound to albumin, _2-macroglobulin, and amino acids in the the plasma. Albumin and amino acid bound zinc can diffuse across tissue membranes. Zinc is excreted in the urine and faeces. (5)
Toxicity ValuesLD50: 18 mg/kg (Intravenous, Mouse) (2) LD50: 23 mg/kg (Intraperitoneal, Rat) (2) LD50: 320 mg/kg (Oral, Rat) (3) LC50: 81 mg/m3 over 4 hours (Inhalation, Rat) (2)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (8)
Uses/SourcesThis is a man-made compound that is used as a pesticide.
Minimum Risk LevelIntermediate Oral: 0.3 mg/kg/day (7) Chronic Oral: 0.3 mg/kg/day (7)
Health EffectsChronic exposure to zinc causes anemia, atazia, lethargy, and decreases the level of good cholesterol in the body. It is also believed to cause pancreatic and reproductive damage. (5)
SymptomsIngestion of large doses of zinc causes stomach cramps, nausea, and vomiting. Acute inhalation of large amounts of zinc causes metal fume fever, which is characterized by chills, fever, headache, weakness, dryness of the nose and throat, chest pain, and coughing. Dermal contact with zinc results in skin irritation. (5)
TreatmentZinc poisoning is treated symptomatically, often by administering fluids such as water or milk, or with gastric lavage. (5)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID8722
ChEMBL IDCHEMBL1519327
ChemSpider ID8397
KEGG IDC15229
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD0-1710
CTD IDD015039
Stitch IDZinc dimethyldithiocarbamate
PDB IDNot Available
ACToR ID1496
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1465.pdf
General References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]
  2. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  3. Tomlin CDS (ed) (1994). The Pesticide Manual - World Compendium. 10th ed. Surrey, UK: The British Crop Protection Council.
  4. Wikipedia. Zinc. Last Updated 24 March 2009. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for zinc. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. Wikipedia. Metallothionein. Last Updated 20 December 2008. [Link]
  7. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  8. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name:
SOD1
Uniprot ID:
P00441
Molecular Weight:
15935.685 Da
References
  1. Vonk WI, Klomp LW: Role of transition metals in the pathogenesis of amyotrophic lateral sclerosis. Biochem Soc Trans. 2008 Dec;36(Pt 6):1322-8. doi: 10.1042/BST0361322. [19021549 ]
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.04 uMTox21_Aromatase_InhibitionTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Not Available
Specific Function:
Not Available
Gene Name:
TP53
Uniprot ID:
P04637
Molecular Weight:
43652.79 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.96 uMAPR_p53Act_24h_upApredica
AC500.20 uMAPR_p53Act_72h_upApredica
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EIF2AK3/PERK. May play an important role in CKII- and p60c-src-induced signal transduction cascades. May regulate the EFNA5-EPHA3 signaling pathway which modulates cell reorganization and cell-cell repulsion. May also regulate the hepatocyte growth factor receptor signaling pathway through dephosphorylation of MET.
Gene Name:
PTPN1
Uniprot ID:
P18031
Molecular Weight:
49966.44 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.53 uMNVS_ENZ_hPTPN1Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth. Involved in chromatin remodeling. May play a negative role in adipogenesis through the regulation of lipolytic and antilipogenic genes expression.
Gene Name:
NR3C1
Uniprot ID:
P04150
Molecular Weight:
85658.57 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC500.87 uMNVS_NR_hGRNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Receptor signaling protein tyrosine kinase activity
Specific Function:
Receptor tyrosine kinase which mediates the pleiotropic actions of insulin. Binding of insulin leads to phosphorylation of several intracellular substrates, including, insulin receptor substrates (IRS1, 2, 3, 4), SHC, GAB1, CBL and other signaling intermediates. Each of these phosphorylated proteins serve as docking proteins for other signaling proteins that contain Src-homology-2 domains (SH2 domain) that specifically recognize different phosphotyrosines residues, including the p85 regulatory subunit of PI3K and SHP2. Phosphorylation of IRSs proteins lead to the activation of two main signaling pathways: the PI3K-AKT/PKB pathway, which is responsible for most of the metabolic actions of insulin, and the Ras-MAPK pathway, which regulates expression of some genes and cooperates with the PI3K pathway to control cell growth and differentiation. Binding of the SH2 domains of PI3K to phosphotyrosines on IRS1 leads to the activation of PI3K and the generation of phosphatidylinositol-(3, 4, 5)-triphosphate (PIP3), a lipid second messenger, which activates several PIP3-dependent serine/threonine kinases, such as PDPK1 and subsequently AKT/PKB. The net effect of this pathway is to produce a translocation of the glucose transporter SLC2A4/GLUT4 from cytoplasmic vesicles to the cell membrane to facilitate glucose transport. Moreover, upon insulin stimulation, activated AKT/PKB is responsible for: anti-apoptotic effect of insulin by inducing phosphorylation of BAD; regulates the expression of gluconeogenic and lipogenic enzymes by controlling the activity of the winged helix or forkhead (FOX) class of transcription factors. Another pathway regulated by PI3K-AKT/PKB activation is mTORC1 signaling pathway which regulates cell growth and metabolism and integrates signals from insulin. AKT mediates insulin-stimulated protein synthesis by phosphorylating TSC2 thereby activating mTORC1 pathway. The Ras/RAF/MAP2K/MAPK pathway is mainly involved in mediating cell growth, survival and cellular differentiation of insulin. Phosphorylated IRS1 recruits GRB2/SOS complex, which triggers the activation of the Ras/RAF/MAP2K/MAPK pathway. In addition to binding insulin, the insulin receptor can bind insulin-like growth factors (IGFI and IGFII). Isoform Short has a higher affinity for IGFII binding. When present in a hybrid receptor with IGF1R, binds IGF1. PubMed:12138094 shows that hybrid receptors composed of IGF1R and INSR isoform Long are activated with a high affinity by IGF1, with low affinity by IGF2 and not significantly activated by insulin, and that hybrid receptors composed of IGF1R and INSR isoform Short are activated by IGF1, IGF2 and insulin. In contrast, PubMed:16831875 shows that hybrid receptors composed of IGF1R and INSR isoform Long and hybrid receptors composed of IGF1R and INSR isoform Short have similar binding characteristics, both bind IGF1 and have a low affinity for insulin.
Gene Name:
INSR
Uniprot ID:
P06213
Molecular Weight:
156331.465 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC501.18 uMNVS_ENZ_hInsR_ActivatorNovascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Atp binding
Specific Function:
Involved in DNA damage response. Involved in a RAD9A-related damage checkpoint, a pathway that is important in determining whether DNA damage is compatible with cell survival or whether it requires cell elimination by apoptosis. Modulates the RAD9A interaction with BCL2 and thereby induces DNA damages-induced apoptosis.
Gene Name:
ATAD5
Uniprot ID:
Q96QE3
Molecular Weight:
207568.185 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC505.56 uMTox21_ELG1_LUC_AgonistTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated proinflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of ARNTL/BMAL1 in the blood vessels (By similarity).
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC507.70 uMTox21_PPARg_BLA_Agonist_ratioTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]