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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H28O5
Molecular Weight 372.4547
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PYRETHRIN II

SMILES

COC(=O)C(\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=VJFUPGQZSXIULQ-XIGJTORUSA-N
InChI=1S/C22H28O5/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8-,13-11+/t16-,18+,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H28O5
Molecular Weight 372.4547
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 2
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. 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. Pyrethrin II has strong activity against Plasmodium falciparum.

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
Patents

Patents

Sample Use Guides

Apply to completelly wet infested areas, leave on 10 min & wash with large amount of warm water Use fine toothed comb to remove lice and egg from hair Do not exceed 2 consecutive applications within 24 hr Retreat in 7-10 days
Route of Administration: Topical
Pyrethrin II showed an IC50 of 4.0 uM against Plasmodium falciparum
Substance Class Chemical
Created
by admin
on Fri Dec 15 14:58:43 GMT 2023
Edited
by admin
on Fri Dec 15 14:58:43 GMT 2023
Record UNII
5N9245585U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRETHRIN II
HSDB   ISO   MI   WHO-DD  
Common Name English
PYRETHRIN II [ISO]
Common Name English
Pyrethrin ii [WHO-DD]
Common Name English
(Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL (E)-(1R,3R)-3-(2-METHOXYCARBONYLPROP-1-ENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
Systematic Name English
PYRETHRIN II [HSDB]
Common Name English
(1S)-2-METHYL-4-OXO-3-(2Z)-2,4-PENTADIENYL-2-CYCLOPENTEN-1-YL (1R,3R)-3-((1E)-3-METHOXY-2-METHYL-3-OXO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
Systematic Name English
PYRETHRIN II [MI]
Common Name English
(Z)-(S)-2-METHYL-4-OXO-3-(PENTA-2,4-DIENYL)CYCLOPENT-2-ENYL PYRETHRATE
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 69006
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
204-462-6
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
EVMPD
SUB15057MIG
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
PUBCHEM
5281555
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
MERCK INDEX
m9345
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY Merck Index
ALANWOOD
pyrethrin II
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
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WIKIPEDIA
PYRETHRIN II
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
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CAS
121-29-9
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
SMS_ID
100000078911
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
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FDA UNII
5N9245585U
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
CHEBI
27474
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
MESH
C009119
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
HSDB
6303
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID2042353
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY