Record Information
Version2.0
Creation Date2009-06-19 21:58:29 UTC
Update Date2014-12-24 20:23:28 UTC
Accession NumberT3D1240
Identification
Common NameTrimethyltin chloride
ClassSmall Molecule
DescriptionTributyltin chloride is an organotin compound. Tributyltins are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and are also used in wood preservation, marine paints (as antifouling pesticides), and textiles and industrial water systems (as antifungal agents). They also considered moderately to highly persistent organic pollutants and are especially hazardous to marine ecosystems. The main toxic component of tributyltins is tin. Tin is a chemical element with the symbol Sn and atomic number 50. It is a natural component of the earth's crust and is obtained chiefly from the mineral cassiterite, where it occurs as tin dioxide. (4, 6, 5)
Compound Type
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organometallic
  • Pesticide
  • Pollutant
  • Synthetic Compound
  • Tin Compound
Chemical Structure
Thumb
Synonyms
Synonym
Chloro(trimethyl)stannane
Chlorotrimethylstannane
Chlorotrimethyltin
Rimethyltin monochloride
Stannylium, trimethyl-, chloride
Tin(+), trimethyl-, chloride
Tin(1+), trimethyl-, chloride
Trimethylchlorostannane
Trimethylchlorotin
Trimethylstannyl chloride
Trimethyltin monochloride
Chemical FormulaC3H9ClSn
Average Molecular Mass199.270 g/mol
Monoisotopic Mass199.941 g/mol
CAS Registry Number1066-45-1
IUPAC Namechlorotrimethylstannane
Traditional Nametrimethyltin chloride
SMILESC[Sn](C)(C)Cl
InChI IdentifierInChI=1S/3CH3.ClH.Sn/h3*1H3;1H;/q;;;;+1/p-1
InChI KeyInChIKey=KWTSZCJMWHGPOS-UHFFFAOYSA-M
Chemical Taxonomy
Description belongs to the class of organic compounds known as triorganotin halide salts. These are organic compounds containing a tin atom bonded to three carbon atoms and a halogen atom.
KingdomOrganic compounds
Super ClassOrganic salts
ClassOrganic metal salts
Sub ClassOrganic post-transition metal salts
Direct ParentTriorganotin halide salts
Alternative Parents
Substituents
  • Triorganotin halide salt
  • Trialkyltin
  • Metal alkyl halide
  • Hydrocarbon derivative
  • Organotin compound
  • Organometallic compound
  • Organic post-transition metal moeity
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point38.5°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.9 g/LALOGPS
logP1.44ALOGPS
logP1.01ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.48 m³·mol⁻¹ChemAxon
Polarizability11.73 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-0090000000-021ebf976ad34f4cf3662019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0090000000-9fbc121a90832ec787902019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1090000000-953ac5e75588a58f77ed2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0900000000-4243855f2b089be3d8182019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-33c98296c9e93b99f5082019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-0900000000-0633c8dc50346d34d2572019-02-23View Spectrum
Toxicity Profile
Route of ExposureOral (5) ; inhalation (5) ; dermal (5)
Mechanism of ToxicityOrganotin compounds produce neurotoxic and immunotoxic effects. Organotins may directly activate glial cells contributing to neuronal cell degeneration by local release of pro-inflammatory cytokines, tumor necrosis factor-_, and/or interleukins. They may also induce apoptosis by direct action on neuronal cells. Organotin compounds stimulate the neuronal release of and/or decrease of neuronal cell uptake of neurotransmitters in brain tissue, including aspartate, GABA, glutamate, norepinephrine, and serotonin. This may be either a contributing factor to or result of the neuronal cell loss. The immunotoxic effects of organotins are characterized by thymic atrophy caused by the suppression of proliferation of immature thymocytes and apoptosis of mature thymocytes. Organotin compounds are believed to exert these effects by suppressing DNA and protein synthesis, inducing the expression of genes involved in apoptosis (such as nur77), and disrupting the regulation of intracellular calcium levels, giving rise to the uncontrolled production of reactive oxygen species, release of cytochrome c to the cytosol, and the proteolytic and nucleolytic cascade of apoptosis. The suppression of proliferation of immature thymocytes further results in the suppression of T-cell-mediated immune responses. Organotins are also endocrine disruptors and are believed to contribute to obesity by inappropriate receptor activation, leading to adipocyte differentiation. Inorganic tin triggers eryptosis, contributing to tin-induced anemia. (5, 1, 2)
MetabolismThough tin metal is very poorly absorbed, tin compounds may be absorbed via oral, inhalation, or dermal routes, with organotin compounds being much more readily absorbed than inorganic tin compounds. Tin may enter the bloodstream and bind to hemoglobin, where it is distributed and accumulates mainly in the kidney, liver, lung, and bone. Organotin compounds may undergo dealkylation, hydroxylation, dearylation, and oxidation catalyzed by cytochrome P-450 enzymes in the liver. The alkyl products of dealkylation are conjugated with glutathione and further metabolized to mercapturic acid derivatives. Tin and its metabolites are excreted mainly in the urine and feces. (5)
Toxicity ValuesLD50: 12 600 ug/kg (Oral, Rat) (3) LD50: 7450 ug/kg (Intraperitoneal, Rat) (3) LD50: 1800 ug/kg (Intravenous, Mouse) (3)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTributyltins are the main active ingredients in certain biocides used to control a broad spectrum of organisms, and are also used in wood preservation, marine paints (as antifouling pesticides), and textiles and industrial water systems (as antifungal agents). (4)
Minimum Risk LevelNot Available
Health EffectsBreathing or swallowing, or skin contact with organotins, can interfere with the way the brain and nervous system work, causing death in severe cases. Organic tin compounds may also damage the immune and reproductive system. (4, 5)
SymptomsInorganic or organic tin compounds placed on the skin or in the eyes can produce skin and eye irritation. (5)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID14016
ChEMBL IDNot Available
ChemSpider ID13398
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC040533
Stitch IDTrimethyltin chloride
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1240.pdf
General References
  1. Nguyen TT, Foller M, Lang F: Tin triggers suicidal death of erythrocytes. J Appl Toxicol. 2009 Jan;29(1):79-83. doi: 10.1002/jat.1390. [18937211 ]
  2. Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
  3. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  4. Wikipedia. Tributyltin. Last Updated 31 May 2009. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for tin. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  6. Wikipedia. Tin. Last Updated 28 May 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular Weight:
39858.37 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular Weight:
39854.21 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH1C
Uniprot ID:
P00326
Molecular Weight:
39867.27 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular Weight:
40221.335 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular Weight:
39088.335 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Could function in retinol oxidation for the synthesis of retinoic acid, a hormone important for cellular differentiation. Medium-chain (octanol) and aromatic (m-nitrobenzaldehyde) compounds are the best substrates. Ethanol is not a good substrate but at the high ethanol concentrations reached in the digestive tract, it plays a role in the ethanol oxidation and contributes to the first pass ethanol metabolism.
Gene Name:
ADH7
Uniprot ID:
P40394
Molecular Weight:
41480.985 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
General Function:
Zinc ion binding
Specific Function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular Weight:
39723.945 Da
References
  1. Bychkov PV, Shekhovtsova TN, Milaeva ER: Inhibition of horse liver alcohol dehydrogenase by methyltin compounds. Bioinorg Chem Appl. 2005:191-9. doi: 10.1155/BCA.2005.191. [18365099 ]
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
References
  1. Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
General Function:
Threonine-type endopeptidase activity
Specific Function:
The proteasome is a multicatalytic proteinase complex which is characterized by its ability to cleave peptides with Arg, Phe, Tyr, Leu, and Glu adjacent to the leaving group at neutral or slightly basic pH. The proteasome has an ATP-dependent proteolytic activity. This unit is responsible of the chymotrypsin-like activity of the proteasome and is one of the principal target of the proteasome inhibitor bortezomib. May catalyze basal processing of intracellular antigens. Plays a role in the protection against oxidative damage through the Nrf2-ARE pathway (By similarity).
Gene Name:
PSMB5
Uniprot ID:
P28074
Molecular Weight:
28480.01 Da
References
  1. Shi G, Chen D, Zhai G, Chen MS, Cui QC, Zhou Q, He B, Dou QP, Jiang G: The proteasome is a molecular target of environmental toxic organotins. Environ Health Perspect. 2009 Mar;117(3):379-86. doi: 10.1289/ehp.11865. Epub 2008 Oct 23. [19337512 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone acetylation, chromatin condensation and transcriptional suppression. On ligand binding, the corepressors dissociate from the receptors and associate with the coactivators leading to transcriptional activation. RARA plays an essential role in the regulation of retinoic acid-induced germ cell development during spermatogenesis. Has a role in the survival of early spermatocytes at the beginning prophase of meiosis. In Sertoli cells, may promote the survival and development of early meiotic prophase spermatocytes. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function (By similarity). Regulates expression of target genes in a ligand-dependent manner by recruiting chromatin complexes containing KMT2E/MLL5. Mediates retinoic acid-induced granulopoiesis.
Gene Name:
RARA
Uniprot ID:
P10276
Molecular Weight:
50770.805 Da
References
  1. Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of hormone ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. In concert with RARG, required for skeletal growth, matrix homeostasis and growth plate function.
Gene Name:
RARB
Uniprot ID:
P10826
Molecular Weight:
50488.63 Da
References
  1. Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts mainly as an activator of gene expression due to weak binding to corepressors. Required for limb bud development. In concert with RARA or RARB, required for skeletal growth, matrix homeostasis and growth plate function (By similarity).
Gene Name:
RARG
Uniprot ID:
P13631
Molecular Weight:
50341.405 Da
References
  1. Grun F, Blumberg B: Environmental obesogens: organotins and endocrine disruption via nuclear receptor signaling. Endocrinology. 2006 Jun;147(6 Suppl):S50-5. Epub 2006 May 11. [16690801 ]