Bromoacetone
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Basic Info
Common Name | Bromoacetone(F04344) |
2D Structure | |
Description | Bromoacetone is an organobromide compound. It is a lachrymatory agent and was used in World War I as a chemical weapon (called BA by British and B-Stoff by Germans) and later as a riot control agent. Today it is considered obsolete (due to its toxicity) and is no longer in use for riot control purposes, but is a useful reagent in organic synthesis. Bromoacetone is prepared by combining bromine and acetone with a catalytic acid such as sulfuric acid. Bromoacetone has been shown to be a by-product of drinking water treatment using chlorine dioxide and chloramines in water high in bromide concentrations. Bromoacetone is found in the essential oil of a seaweed species (Asparagopsis taxiformis) that grows in the ocean around the Hawaiian Islands. Bromoacetone is structurally similar to chloroacetone. Both chemicals are irritants however, data suggest that bromoacetone is more toxic than chloroacetone. As a chemical warfare or riot control agent, bromoacetone is/was considered to be a rapid acting casualty producing agent capable of causing casualties within minutes of dissemination. Eye exposure to as little as 1 mg can cause pain and irritation. Inhalation of as little as 2-5 mg can cause coughing, nose and throat irritation and congestion. Inhalation of higher concentrations may lead to severe sore throat, nasal congestion and serious discomfort. Skin contact with as little as 2-30 mg can produce irritation, itching, swelling and general discomfort. Skin exposure to 50-100mg may lead to blisters. |
FRCD ID | F04344 |
CAS Number | 598-31-2 |
PubChem CID | 11715 |
Formula | C3H5BrO |
IUPAC Name | 1-bromopropan-2-one |
InChI Key | VQFAIAKCILWQPZ-UHFFFAOYSA-N |
InChI | InChI=1S/C3H5BrO/c1-3(5)2-4/h2H2,1H3 |
Canonical SMILES | CC(=O)CBr |
Isomeric SMILES | CC(=O)CBr |
Synonyms | BROMOACETONE Bromo-2-propanone 1-Bromo-2-propanone 598-31-2 Monobromoacetone Acetonyl bromide Martonite 1-bromopropan-2-one 2-Propanone, 1-bromo- 1-Bromoacetone |
Classifies | Plant Toxin |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic oxygen compounds |
Class | Organooxygen compounds |
Subclass | Carbonyl compounds |
Intermediate Tree Nodes | Ketones |
Direct Parent | Alpha-haloketones |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Alpha-haloketone - Organic oxide - Hydrocarbon derivative - Organobromide - Organohalogen compound - Alkyl halide - Alkyl bromide - Aliphatic acyclic compound |
Description | This compound belongs to the class of organic compounds known as alpha-haloketones. These are organic compounds contaning a halogen atom attached to the alpha carbon atom relative to C=O group. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 136.976 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 1 |
Rotatable Bond Count | 1 |
Complexity | 42.2 |
Monoisotopic Mass | 135.952 |
Exact Mass | 135.952 |
XLogP | 0.7 |
Formal Charge | 0 |
Heavy Atom Count | 5 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9894 |
Human Intestinal Absorption | HIA+ | 1.0000 |
Caco-2 Permeability | Caco2+ | 0.7386 |
P-glycoprotein Substrate | Non-substrate | 0.8263 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9197 |
Non-inhibitor | 0.9286 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8718 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6569 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8099 |
CYP450 2D6 Substrate | Non-substrate | 0.8509 |
CYP450 3A4 Substrate | Non-substrate | 0.6921 |
CYP450 1A2 Inhibitor | Inhibitor | 0.5120 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9295 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9407 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.8610 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9407 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9126 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9296 |
Non-inhibitor | 0.9436 | |
AMES Toxicity | AMES toxic | 0.7915 |
Carcinogens | Carcinogens | 0.7698 |
Fish Toxicity | Low FHMT | 0.7591 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9402 |
Honey Bee Toxicity | High HBT | 0.7670 |
Biodegradation | Ready biodegradable | 0.5859 |
Acute Oral Toxicity | II | 0.5434 |
Carcinogenicity (Three-class) | Non-required | 0.5529 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.1006 | LogS |
Caco-2 Permeability | 1.4854 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 3.1016 | LD50, mol/kg |
Fish Toxicity | 1.3890 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.8772 | pIGC50, ug/L |
Targets
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Garner CE, Sumner SC, Davis JG, Burgess JP, Yueh Y, Demeter J, Zhan Q, Valentine J, Jeffcoat AR, Burka LT, Mathews JM: Metabolism and disposition of 1-bromopropane in rats and mice following inhalation or intravenous administration. Toxicol Appl Pharmacol. 2006 Aug 15;215(1):23-36. Epub 2006 Mar 2. [16513153 ]