Trimethylthiazoline

Trimethylthiazoline
Names
	IUPAC name 2,4,5-Trimethyl-4,5-dihydro-1,3-thiazole
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	231591;
PubChem CID	263626;
CompTox Dashboard (EPA)	DTXSID20294803 DTXSID50945917, DTXSID20294803 ;
	InChI InChI=1S/C6H11NS/c1-4-5(2)8-6(3)7-4/h4-5H,1-3H3 Key: CIEKNJJOENYFQL-UHFFFAOYSA-N;
	SMILES CC1C(SC(=N1)C)C;
Properties
Chemical formula	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 ?) Infobox references

Trimethylthiazoline (TMT or 2,5-dihydro-2,4,5-trimethylthiazoline) is a constituent of fox urine that is an innately aversive odor to rodents. The chemical is liquid at room temperature and has a very light yellow color which darkens on oxygen exposure over time.

Discovered by Vernet-Maury in 1980 as the major compound for inducing antipredator behavior in rats.^[1] However, 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]

Research

Researchers at SRQBio were able to synthesize TMT and use it with a combination of other stressors such as foot shocks/loud noises as a natural predator psychogenic stress to study posttraumatic stress disorder in rodents.^[4] 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.^[5]

References

^ Fendt, Markus; Endres, Thomas; Lowry, Catherine A.; Apfelbach, Raimund; McGregor, Iain S. (2005-01-01). "TMT-induced autonomic and behavioral changes and the neural basis of its processing". Neuroscience & Biobehavioral Reviews. Defensive Behavior. 29 (8): 1145–1156. doi:10.1016/j.neubiorev.2005.04.018.
^ MUSSINAN, CYNTHIA J.; WILSON, RICHARD A.; KATZ, IRA; HRUZA, ANNE; VOCK, MANFRED H. (1976-06-01). Phenolic, Sulfur, and Nitrogen Compounds in Food Flavors. ACS Symposium Series. Vol. 26. AMERICAN CHEMICAL SOCIETY. pp. 133–145. doi:10.1021/bk-1976-0026.ch009. ISBN 084120330X.
^ Bredie, Wender L. P.; Mottram, Donald S.; Guy, Robin C. E. (2002-02-27). "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): 1118–1125. ISSN 0021-8561. PMID 11853492.
^ "Trimethylthiazoline (TMT - a component of fox feces/urine)".
^ Goswami, S; Rodríguez-Sierra, O (2013). "Animal models of post-traumatic stress disorder: face validity". Frontiers in Neuroscience. doi:10.3389/fnins.2013.00089.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1] Fendt, Markus; Endres, Thomas; Lowry, Catherine A.; Apfelbach, Raimund; McGregor, Iain S. (2005-01-01). "TMT-induced autonomic and behavioral changes and the neural basis of its processing". Neuroscience & Biobehavioral Reviews. Defensive Behavior. 29 (8): 1145–1156. doi:10.1016/j.neubiorev.2005.04.018.

[2] MUSSINAN, CYNTHIA J.; WILSON, RICHARD A.; KATZ, IRA; HRUZA, ANNE; VOCK, MANFRED H. (1976-06-01). Phenolic, Sulfur, and Nitrogen Compounds in Food Flavors. ACS Symposium Series. Vol. 26. AMERICAN CHEMICAL SOCIETY. pp. 133–145. doi:10.1021/bk-1976-0026.ch009. ISBN 084120330X.

[3] Bredie, Wender L. P.; Mottram, Donald S.; Guy, Robin C. E. (2002-02-27). "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): 1118–1125. ISSN 0021-8561. PMID 11853492.

[4] "Trimethylthiazoline (TMT - a component of fox feces/urine)".

[5] Goswami, S; Rodríguez-Sierra, O (2013). "Animal models of post-traumatic stress disorder: face validity". Frontiers in Neuroscience. doi:10.3389/fnins.2013.00089.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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