Chemistry:Trimethylthiazoline
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| Names | |
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| Preferred IUPAC name
2,4,5-Trimethyl-4,5-dihydro-1,3-thiazole | |
| Other names
Fox odor
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H11NS | |
| Molar mass | 129.22 g·mol−1 |
| Appearance | Light yellow liquid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 (what is   ?)
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| Infobox references | |
Trimethylthiazoline (TMT; sometimes called fox odor) is a constituent of fox urine and feces that may be an innately aversive odor to rodents.[1] The chemical is liquid at room temperature and has a very light yellow color which darkens on oxygen exposure over time.
Sources
TMT was first isolated from cooked beef in 1977,[2] and has been identified also in non-animal material such as wheat flour extrudates.[3] It was identified in fox feces by Vernet-Maury in 1980.[4]
Effects
Vernet-Maury reported that TMT is effective at inducing antipredator behavior in rats.[5]
TMT has been called an "innate threat stimulus" because of how it "induces a number of fear and defensive behaviors" in naive mice and rats.[6]
Not all research has come to the same conclusions, however; with some questioning the role of TMT in the aversive effects of fox feces.[7][8] One study, for example, found that cat odor, but not TMT, elicits specific defensive behaviors in rats.[9]
Immunoprecipitation of RNA transcripts of murine olfactory cells have identified an enriched pool of odorant receptors activated by TMT, including five receptors (Olfr20, Olfr30, Olfr57, Olfr376, Olfr491) that localize to the dorsal portion of the olfactory epithelium which can mediate fear behaviour.[10]
References
- ↑ "The smell of fear: innate threat of 2,5-dihydro-2,4,5-trimethylthiazoline, a single molecule component of a predator odor". Frontiers in Neuroscience 9: 292. 2015. doi:10.3389/fnins.2015.00292. PMID 26379483.
- ↑ Mussinan, Cynthia J; Wilson, Richard A; Katz, IRA; Hruza, Anne; Vock, Manfred H (1976). "Identification and Flavor Properties of Some 3-Oxazolines and 3-Thiazolines Isolated from Cooked Beef". Phenolic, Sulfur, and Nitrogen Compounds in Food Flavors. ACS Symposium Series. 26. pp. 133–145. doi:10.1021/bk-1976-0026.ch009. ISBN 0-8412-0330-X. https://archive.org/details/phenolicsulfurni00char_0/page/133.
- ↑ "Effect of temperature and pH on the generation of flavor volatiles in extrusion cooking of wheat flour". Journal of Agricultural and Food Chemistry 50 (5): 1118–25. February 2002. doi:10.1021/jf0111662. PMID 11853492.
- ↑ "Structure-activity relationship of stress-inducing odorants in the rat". Journal of Chemical Ecology 10 (7): 1007–18. July 1984. doi:10.1007/BF00987509. PMID 24318845.
- ↑ "TMT-induced autonomic and behavioral changes and the neural basis of its processing". Neuroscience and Biobehavioral Reviews 29 (8): 1145–56. 2005. doi:10.1016/j.neubiorev.2005.04.018. PMID 16099043.
- ↑ "Animal models of post-traumatic stress disorder: face validity". Frontiers in Neuroscience 7: 89. 2013. doi:10.3389/fnins.2013.00089. PMID 23754973.
- ↑ "Where is the TMT? GC-MS analyses of fox feces and behavioral responses of rats to fear-inducing odors". Chemical Senses 43 (2): 105–115. February 2018. doi:10.1093/chemse/bjx075. PMID 29228118.
- ↑ "Failure to produce conditioning with low-dose trimethylthiazoline or cat feces as unconditioned stimuli". Behavioral Neuroscience 117 (2): 360–8. April 2003. doi:10.1037/0735-7044.117.2.360. PMID 12708532.
- ↑ "Not all 'predator odours' are equal: cat odour but not 2,4,5 trimethylthiazoline (TMT; fox odour) elicits specific defensive behaviours in rats". Behavioural Brain Research 129 (1–2): 1–16. February 2002. doi:10.1016/S0166-4328(01)00324-2. PMID 11809490.
- ↑ "Molecular profiling of activated olfactory neurons identifies odorant receptors for odors in vivo". Nature Neuroscience 18 (10): 1446–54. October 2015. doi:10.1038/nn.4104. PMID 26322927.
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