Methylcyclopentadienyl manganese tricarbonyl (CHEM000970)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-06-19 21:58:21 UTC
Update Date2026-04-03 06:50:28 UTC
Accession NumberCHEM000970
Identification
Common NameMethylcyclopentadienyl manganese tricarbonyl
ClassSmall Molecule
DescriptionMethylcyclopentadienyl manganese tricarbonyl (MMT) is a chemical compound of manganese. It was initially used as a supplement to the gasoline additive tetraethyl lead to increase a fuel's octane rating, then later also used in unleaded gasoline. It has been banned in various countries in the past due to its toxicity, but is available in most places today, despite controvery over its safety. Manganese is a naturally occurring metal with the symbol Mn and the atomic number 25. It does not occur naturally in its pure form, but is found in many types of rocks in combination with other substances such as oxygen, sulfur, or chlorine. Manganese occurs naturally in most foods and small amounts are needed to stay healthy, as manganese ions act as cofactors for a number of enzymes. (3, 4, 5)
Contaminant Sources
  • Clean Air Act Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Food Toxin
  • Household Toxin
  • Manganese Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC9H7MnO3
Average Molecular Mass218.088 g/mol
Monoisotopic Mass217.978 g/mol
CAS Registry Number12108-13-3
IUPAC Name2-methylcyclopenta-2,4-dien-1-yl tris(methanidylidyneoxidanium) manganese
Traditional Name2-methylcyclopenta-2,4-dien-1-yl tris(carbon monoxide) manganese
SMILES[Mn].[C-]#[O+].[C-]#[O+].[C-]#[O+].CC1=CC=C[CH]1
InChI IdentifierInChI=1S/C6H7.3CO.Mn/c1-6-4-2-3-5-6;3*1-2;/h2-5H,1H3;;;;
InChI KeyLYHJNAIHGFWRKM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cycloalkenes. These are unsaturated monocyclic hydrocarbons having one endocyclic double bond.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassOlefins
Direct ParentCycloalkenes
Alternative Parents
Substituents
  • Organic transition metal salt
  • Cycloalkene
  • Organic oxygen compound
  • Unsaturated aliphatic hydrocarbon
  • Hydrocarbon derivative
  • Organic salt
  • Aliphatic homomonocyclic compound
Molecular FrameworkNot Available
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
StateLiquid
AppearanceYellow to dark orange liquid.
Experimental Properties
PropertyValue
Melting Point1.5°C
Boiling PointNot Available
Solubility0.029 mg/mL at 25°C [GARRISON,AW et al. (1995)]
Predicted Properties
PropertyValueSource
Water Solubility8.04 g/LALOGPS
logP2.21ALOGPS
logP1.55ChemAxon
logS-1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.31 m³·mol⁻¹ChemAxon
Polarizability9.47 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-618af413accb30414c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-618af413accb30414c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0090000000-618af413accb30414c94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-f9b84666ff8e388846d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-f9b84666ff8e388846d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-0090000000-f9b84666ff8e388846d9Spectrum
Toxicity Profile
Route of ExposureOral (3) ; inhalation (3)
Mechanism of ToxicityManganese is a cellular toxicant that can impair transport systems, enzyme activities, and receptor functions. It primarily targets the central nervous system, particularily the globus pallidus of the basal ganglia. It is believed that the manganese ion, Mn(II), enhances the autoxidation or turnover of various intracellular catecholamines, leading to increased production of free radicals, reactive oxygen species, and other cytotoxic metabolites, along with a depletion of cellular antioxidant defense mechanisms, leading to oxidative damage and selective destruction of dopaminergic neurons. In addition to dopamine, manganese is thought to perturbations other neurotransmitters, such as GABA and glutamate. In order to produce oxidative damage, manganese must first overwhelm the antioxidant enzyme manganese superoxide dismutase. The neurotoxicity of Mn(II) has also been linked to its ability to substitute for Ca(II) under physiological conditions. It can enter mitochondria via the calcium uniporter and inhibit mitochondrial oxidative phosphorylation. It may also inhibit the efflux of Ca(II), which can result in a loss of mitochondrial membrane integrity. Mn(II) has been shown to inhibit mitochondrial aconitase activity to a significant level, altering amino acid metabolism and cellular iron homeostasis. (3)
MetabolismManganese is absorbed mainly via ingestion, but can also be inhaled. It binds to alpha-2-macroglobulin, albumin, or transferrin in the plasma and is distributed to the brain and all other mammalian tissues, though it tends to accumulate more in the liver, pancreas, and kidney. MMT is metabolized by cytochrome P-450 enzymes into hydroxylmethylcyclopentadienyl manganese tricarbonyl and carboxycyclopentadienyl manganese tricarbonyl. These metabolites are excreted in the urine and faeces. (3)
Toxicity ValuesLD50: 140-795 mg/kg (Dermal, Rabbit) (6) LD50: 58 mg/kg (Oral, Rat) (1) LC50: 247 mg/m3 over 1 hour (Inhalation, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMethylcyclopentadienyl manganese tricarbonyl (MMT) is a chemical compound of manganese. It was initially used as a supplement to the gasoline additive tetraethyl lead to increase a fuel's octane rating, then later also used in unleaded gasoline. It has been banned in various countries in the past due to its toxicity, but is available in most places today, despite controvery over its safety. (5)
Minimum Risk LevelChronic Inhalation: 0.0003 mg/m3 (2)
Health EffectsManganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (3)
SymptomsManganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (3)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMethylcyclopentadienyl manganese tricarbonyl
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID10921955
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available