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{{Chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 430484221 | verifiedrevid = 446675741
| ImageFile = VUAA1_structure.png | ImageFile = VUAA1_structure.svg
| ImageSize = 250px | ImageSize = 200px
| IUPACName = 2-(4-ethyl-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-ylthio)-N-(4-ethylphenyl)acetamide | PIN = ''N''-(4-Ethylphenyl)-2-<nowiki/>{sulfanyl}acetamide
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = | CASNo = 525582-84-7
⚫ | SMILES = CCN1C(C2=CN=CC=C2)=NN=C1SCC(NC3=CC=C(CC)C=C3)=O
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 1319135
| UNII = ZZ52US95LQ
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES = CCN1C(C2=CN=CC=C2)=NN=C1SCC(NC3=CC=C(CC)C=C3)=O
⚫ | PubChem = 1319135
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1105882 | ChemSpiderID = 1105882
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UWCCKVJVOHTHAF-UHFFFAOYSA-N | StdInChIKey = UWCCKVJVOHTHAF-UHFFFAOYSA-N
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI=1S/C19H21N5OS/c1-3-14-7-9-16(10-8-14)21-17(25)13-26-19-23-22-18(24(19)4-2)15-6-5-11-20-12-15/h5-12H,3-4,13H2,1-2H3,(H,21,25) | StdInChI=1S/C19H21N5OS/c1-3-14-7-9-16(10-8-14)21-17(25)13-26-19-23-22-18(24(19)4-2)15-6-5-11-20-12-15/h5-12H,3-4,13H2,1-2H3,(H,21,25)
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=19
| Formula = C<sub>19</sub>H<sub>21</sub>N<sub>5</sub>OS
| H=21
| MolarMass = 367.468
| N=5
| Appearance =
| Density = | O=1
| S=1
⚫ | MeltingPt =
| BoilingPt = | Appearance =
| Solubility = | Density =
⚫ | MeltingPt =
| BoilingPt =
| Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
⚫ | MainHazards =
| GHSSignalWord = Warning
⚫ | FlashPt =
| HPhrases = {{H-phrases|315|319|335}}
| Autoignition =
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
⚫ | MainHazards =
⚫ | FlashPt =
| AutoignitionPt =
}} }}
}} }}


'''VUAA1''' is a chemical compound that works by over activating an insect's ]s causing a ] effect. It was recently discovered at ].<ref>Jones PL, Pask GM, Rinker DC, Zwiebel LJ. Functional agonism of insect odorant receptor ion channels. ''Proceedings of the National Academy of Sciences USA''. 2011 May 9. PMID 21555561</ref> '''VUAA1''' is a chemical compound that works by over activating an insect's ]s causing a ] effect. It is considered to be an Orco allosteric agonist.<ref>{{Cite web|url=https://medschool.vanderbilt.edu/syncore/publication/allosteric-antagonism-insect-odorant-receptor-ion-channels|title=Allosteric antagonism of insect odorant receptor ion channels. {{!}} Chemical Synthesis Core|last=Medicine|first=Vanderbilt University School of|website=medschool.vanderbilt.edu|access-date=2016-06-02}}</ref> It was discovered at ]<ref>{{Cite journal | pmid=21555561| pmc=3102409| year=2011| last1=Jones| first1=P. L.| title=Functional agonism of insect odorant receptor ion channels| journal=Proceedings of the National Academy of Sciences| volume=108| issue=21| pages=8821–5| last2=Pask| first2=G. M.| last3=Rinker| first3=D. C.| last4=Zwiebel| first4=L. J.| doi=10.1073/pnas.1102425108| bibcode=2011PNAS..108.8821J| doi-access=free}}</ref> with research being partially funded by the ].<ref>{{Cite web|url=http://www.cnn.com/2014/05/05/tech/innovation/big-idea-bug-spray/index.html|title=A bug repellent that could save lives - CNN.com|author=Doug Gross|website=CNN|date=5 May 2014|access-date=2016-06-02}}</ref>


VUAA1 is first-in-class agonist believed to work by overloading an insect's ]s. This new class of chemicals is said to be 1000 times stronger than ]<ref name="physorg05">{{cite press release | title = New type of insect repellent may be thousands of times stronger than DEET | date= May 9, 2011 | publisher = physorg.com | url = http://www.physorg.com/news/2011-05-biologists-class-insect-repellent.html}}</ref> and may lead to, "a powerful new family of compounds that can be used to disrupt the destructive behaviors of nuisance insects, agricultural pests, and ]s alike."<ref>{{cite press release | title = Functional agonism of insect odorant receptor ion channel | date= April 4, 2011 | url=http://www.pnas.org/content/early/2011/05/04/1102425108.full.pdf+html}}</ref> VUAA1 is an ] believed to work by overloading an insect's ]s. It may be 1000 times stronger than ]<ref name="physorg05">{{cite press release | title = New type of insect repellent may be thousands of times stronger than DEET | date= May 9, 2011 | publisher = physorg.com | url = http://www.physorg.com/news/2011-05-biologists-class-insect-repellent.html}}</ref> and may lead to, "a powerful new family of compounds that can be used to disrupt the destructive behaviors of nuisance insects, agricultural pests, and ]s alike."<ref>{{cite press release | title = Functional agonism of insect odorant receptor ion channel | date= April 4, 2011 | url=http://www.pnas.org/content/early/2011/05/04/1102425108.full.pdf+html}}</ref>

VUAA1 has also been shown to stimulate mosquito sperm motility, thus showing a link between a mosquito's sense of smell and reproduction.<ref>{{Cite web|url=http://www.vanderbilt.edu/vicb/DiscoveriesArchives/linking_sense_smell.html|title=VICB Article: Sulfilimine Cross-Links A Key to Tissue Evolution|website=www.vanderbilt.edu|access-date=2016-06-02}}</ref>


== References == == References ==
<!--- See ] on how to create references using <ref></ref> tags which will then appear here automatically -->
{{Reflist}} {{Reflist}}


== External links == == External links ==
* *


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Latest revision as of 16:48, 7 November 2022

VUAA1
Names
Preferred IUPAC name N-(4-Ethylphenyl)-2-{sulfanyl}acetamide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H21N5OS/c1-3-14-7-9-16(10-8-14)21-17(25)13-26-19-23-22-18(24(19)4-2)15-6-5-11-20-12-15/h5-12H,3-4,13H2,1-2H3,(H,21,25)Key: UWCCKVJVOHTHAF-UHFFFAOYSA-N
SMILES
  • CCN1C(C2=CN=CC=C2)=NN=C1SCC(NC3=CC=C(CC)C=C3)=O
Properties
Chemical formula C19H21N5OS
Molar mass 367.47 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

VUAA1 is a chemical compound that works by over activating an insect's olfactory senses causing a repellent effect. It is considered to be an Orco allosteric agonist. It was discovered at Vanderbilt University with research being partially funded by the Bill and Melinda Gates Foundation.

VUAA1 is an agonist believed to work by overloading an insect's odorant receptors. It may be 1000 times stronger than DEET and may lead to, "a powerful new family of compounds that can be used to disrupt the destructive behaviors of nuisance insects, agricultural pests, and disease vectors alike."

VUAA1 has also been shown to stimulate mosquito sperm motility, thus showing a link between a mosquito's sense of smell and reproduction.

References

  1. Medicine, Vanderbilt University School of. "Allosteric antagonism of insect odorant receptor ion channels. | Chemical Synthesis Core". medschool.vanderbilt.edu. Retrieved 2016-06-02.
  2. Jones, P. L.; Pask, G. M.; Rinker, D. C.; Zwiebel, L. J. (2011). "Functional agonism of insect odorant receptor ion channels". Proceedings of the National Academy of Sciences. 108 (21): 8821–5. Bibcode:2011PNAS..108.8821J. doi:10.1073/pnas.1102425108. PMC 3102409. PMID 21555561.
  3. Doug Gross (5 May 2014). "A bug repellent that could save lives - CNN.com". CNN. Retrieved 2016-06-02.
  4. "New type of insect repellent may be thousands of times stronger than DEET" (Press release). physorg.com. May 9, 2011.
  5. "Functional agonism of insect odorant receptor ion channel" (Press release). April 4, 2011.
  6. "VICB Article: Sulfilimine Cross-Links A Key to Tissue Evolution". www.vanderbilt.edu. Retrieved 2016-06-02.

External links

Categories: