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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PYRETHRIN I

SMILES

CC(C)=C[C@@H]1[C@@H](C(=O)O[C@H]2CC(=O)C(C\C=C/C=C)=C2C)C1(C)C

InChI

InChIKey=ROVGZAWFACYCSP-VUMXUWRFSA-N
InChI=1S/C21H28O3/c1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-/t16-,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H28O3
Molecular Weight 328.4452
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Pyrethrins are natural insecticides derived from chrysanthemum flowers containing a mixture of six components: pyrethrin I, cinerin I, jasmolin I, pyrethrin II, cinerin II, and jasmolin II. Pyrethrin I is one of the two pyrethrins, natural organic compounds with potent insecticidal activity. It is an ester of (+)-trans-chrysanthemic acid with (S)-(Z)-pyrethrolone. Pyrethrins induce a toxic effect in insects when they penetrate the cuticle and reach the nervous system. Pyrethrins bind to sodium channels that occur along the length of nerve cells. Sodium channels are responsible for nerve signal transmission along the length of the nerve cell by permitting the flux of sodium ions. When pyrethrins bind to sodium channels, normal function of the channels is obstructed thereby resulting in hyperexcitation of the nerve cell and, consequently, a loss of function of the nerve cell. The shutdown of the insect nervous system and death are most often the consequences of insect exposure to pyrethrins.

Originator

Sources: Journal of the Association of Official Agricultural Chemists (1937), 20, 388-92

Approval Year

PubMed

PubMed

TitleDatePubMed
Antiplasmodial and antitrypanosomal activity of pyrethrins and pyrethroids.
2011 Sep 14
Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination.
2016 Sep 28
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: also used topically http://reference.medscape.com/drug/rid-klout-shampoo-pyrethrins-piperonyl-butoxide-topical-343499
Humans: oral intake of 0.3mg
Route of Administration: Oral
Pyrethrin I showed an IC50 of 6.9 uM against Trypanosoma brucei rhodesiense.
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:42 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:42 GMT 2023
Record UNII
T018I9EQOL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRETHRIN I
HSDB   ISO   MI   WHO-DD  
Common Name English
PYRETHRIN I [HSDB]
Common Name English
Pyrethrin i [WHO-DD]
Common Name English
(Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL (+)-TRANS-CHRYSANTHEMATE
Common Name English
(Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL (1R,3R)-2,2-DIMETHYL-3-(2-METHYLPROP-1-ENYL)CYCLOPROPANECARBOXYLATE
Systematic Name English
PYRETHRIN I [ISO]
Common Name English
PYRETHRIN I [MI]
Common Name English
(1S)-2-METHYL-4-OXO-3-(2Z)-2,4-PENTADIENYLCYCLOPENTEN-1-YL (1R,3R)-2,2-DIMETHYL-3-(2-METHYL-1-PROPENYL)CYCLOPROPANECARBOXYLATE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 69008
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
Code System Code Type Description
EVMPD
SUB15056MIG
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
CAS
121-21-1
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
CHEBI
27815
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
HSDB
6302
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID4034499
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
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ECHA (EC/EINECS)
204-455-8
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
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MESH
C009119
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
WIKIPEDIA
PYRETHRIN I
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
SMS_ID
100000078891
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
MERCK INDEX
m9345
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY Merck Index
FDA UNII
T018I9EQOL
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
ALANWOOD
pyrethrin I
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
PUBCHEM
5281045
Created by admin on Fri Dec 15 14:58:42 GMT 2023 , Edited by admin on Fri Dec 15 14:58:42 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE -> PARENT
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