Trimethylthiazoline

Trimethylthiazoline
Names
Preferred IUPAC name
2,4,5-Trimethyl-2,5-dihydro-1,3-thiazole
Other names
  • 2,4,5-Trimethyl-3-thiazoline
  • Fox odor
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C6H11NS/c1-4-5(2)8-6(3)7-4/h5-6H,1-3H3
    Key: AIVVNNYXOSPRCW-UHFFFAOYSA-N
  • N1=C(C)C(SC1C)C
Properties
C6H11NS
Molar mass 129.22 g·mol−1
Appearance Light yellow liquid
Odor Meaty, nutty, onion-like
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trimethylthiazoline (TMT; sometimes called fox odor; systematic name 2,4,5-trimethyl-2,5-dihydro-1,3-thiazole), is a constituent of fox feces that may be an innately aversive odor to rodents. The chemical is liquid at room temperature and has a very light yellow color that darkens on exposure to oxygen over time.

Sources

TMT was first isolated from cooked beef in 1977, and has been identified also in non-animal material such as wheat flour extrudates. It was identified in fox feces by Vernet-Maury in 1980.

Effects

Vernet-Maury reported that TMT is effective at inducing antipredator behavior in rats.

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.

Not all research has come to the same conclusions, however; with some questioning the role of TMT in the aversive effects of fox feces, or reporting that TMT was only rarely present in fox feces. One study, for example, found that cat odor, but not TMT, elicits specific defensive behaviors in rats.

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.

Notes

  1. ↑ Some sources instead describe the odor of TMT as "powerfully acrid" or "extremely repugnant ... potentially capable of inducing nausea".
  2. ↑ Some sources instead identify TMT with the isomer 4145-93-1 2,4,5-trimethyl-4,5-dihydro-1,3-thiazole, or claim that 2,4,5-trimethyl-2,5-dihydro-1,3-thiazole and 2,4,5-trimethyl-4,5-dihydro-1,3-thiazole are alternate names for the same chemical.

References

  1. 1 2 Mussinan CJ, Wilson RA, Katz I, Hruza A, Vock MH (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. Vol. 26. pp. 133–145. doi:10.1021/bk-1976-0026.ch009. ISBN 0-8412-0330-X.
  2. 1 2 3 4 5 6 Fendt M, Endres T, Lowry CA, Apfelbach R, McGregor IS (2005). "TMT-induced autonomic and behavioral changes and the neural basis of its processing" (PDF). Neuroscience and Biobehavioral Reviews. 29 (8): 1145–56. doi:10.1016/j.neubiorev.2005.04.018. PMID 16099043. S2CID 28347024.
  3. 1 2 Vernet-Maury E, Polak EH, Demael A (July 1984). "Structure-activity relationship of stress-inducing odorants in the rat". Journal of Chemical Ecology. 10 (7): 1007–18. Bibcode:1984JCEco..10.1007V. doi:10.1007/BF00987509. PMID 24318845. S2CID 21326349.
  4. ↑ Rosen JB, Asok A, Chakraborty T (2015). "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. doi:10.3389/fnins.2015.00292. PMC 4548190. PMID 26379483.
  5. ↑ Bredie WL, Mottram DS, Guy RC (February 2002). "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. doi:10.1021/jf0111662. PMID 11853492.
  6. ↑ Goswami S, Rodríguez-Sierra O, Cascardi M, Paré D (2013). "Animal models of post-traumatic stress disorder: face validity". Frontiers in Neuroscience. 7: 89. doi:10.3389/fnins.2013.00089. PMC 3668155. PMID 23754973.
  7. ↑ Blanchard DC, Markham C, Yang M, Hubbard D, Madarang E, Blanchard RJ (April 2003). "Failure to produce conditioning with low-dose trimethylthiazoline or cat feces as unconditioned stimuli". Behavioral Neuroscience. 117 (2): 360–8. doi:10.1037/0735-7044.117.2.360. PMID 12708532.
  8. ↑ Rampin O, Jerôme N, Saint-Albin A, Ouali C, Boué F, Meunier N, Nielsen BL (February 2018). "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. doi:10.1093/chemse/bjx075. PMID 29228118.
  9. ↑ McGregor IS, Schrama L, Ambermoon P, Dielenberg RA (February 2002). "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. doi:10.1016/S0166-4328(01)00324-2. PMID 11809490. S2CID 25158077.
  10. ↑ Jiang Y, Gong NN, Hu XS, Ni MJ, Pasi R, Matsunami H (October 2015). "Molecular profiling of activated olfactory neurons identifies odorant receptors for odors in vivo". Nature Neuroscience. 18 (10): 1446–54. doi:10.1038/nn.4104. PMC 4583814. PMID 26322927.