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Chemistry

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Also known as: 584-79-2, Pynamin, Esbiothrin, D-cis,trans-allethrin, 84030-86-4, Allethrine
Molecular Formula
C19H26O3
Molecular Weight
302.4  g/mol
InChI Key
ZCVAOQKBXKSDMS-UHFFFAOYSA-N
FDA UNII
0X03II877M

Allethrin
Synthetic analogs of the naturally occurring insecticides cinerin, jasmolin, and pyrethrin. (From Merck Index, 11th ed)
1 2D Structure

Allethrin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
2.1.2 InChI
InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
2.1.3 InChI Key
ZCVAOQKBXKSDMS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
2.2 Other Identifiers
2.2.1 UNII
0X03II877M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Allethrins

2. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester

2.3.2 Depositor-Supplied Synonyms

1. 584-79-2

2. Pynamin

3. Esbiothrin

4. D-cis,trans-allethrin

5. 84030-86-4

6. Allethrine

7. D-cis-trans-allethrin

8. D-allethrin

9. Alpha-dl-trans-allethrin

10. Pallethrine

11. Allethrins

12. Pyresin

13. Pyresyn

14. Allethrin I

15. Allyl Cinerin I

16. 22431-63-6

17. Necarboxylic Acid

18. D-t-allethrin

19. D-trans-allethrin

20. Wasp Killer Ii

21. (2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

22. Bioaletrina

23. Cinerin I Allyl Homolog

24. 3-allyl-2-methyl-4-oxo-2-cyclopenten-1-yl Chrysanthemate

25. Chebi:34572

26. Trans-chrysanthemummonocarboxylate

27. Allyl Homolog Of Cinerin I

28. D-allethrolone Chrysanthemumate

29. 42534-61-2

30. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester

31. Fmc 249

32. Ncgc00163953-03

33. Nia 249

34. Fda 1446

35. Ru 16121

36. 3972-20-1

37. (+/-)-allerethonyl (+/-)-cis,trans-chrysanthemate

38. (+)-allethronyl (+)-trans-chrysanthemumate

39. 28434-00-6

40. Ai 3-29024

41. (+)-allelrethonyl (+)-cis,trans-chrysanthemate

42. 3-allyl-4-keto-2-methylcyclopentenyl Chrysanthemum Monocarboxylate

43. Mgk Allethrin Concentrate

44. Allethrolone Ester Of Chrysanthemummonocarboxylic Acid

45. Bioallethrin (ban)

46. (+)-trans-allethrin

47. D-trans Allethrin

48. 3-allyl-2-methyl-4-oxocyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate

49. D-trans-(1-methyl-2-allyl-3-oxo-1-cyclopenten-5-yl)chrysanthemumate

50. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1s)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester, (1r,3r)-

51. Bioallathrin

52. 0x03ii877m

53. Allyl Cinerin

54. Allethrin 1

55. S-trans-bioallethrin

56. (+)-trans-bioallethrin

57. Allethrin [hsdb]

58. Allethrin I [mi]

59. Dsstox_cid_15180

60. Dsstox_rid_79245

61. Duocide [veterinary] (tn)

62. Dsstox_gsid_35180

63. Schembl26963

64. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester, (1-alpha(s*),3-beta)-(+-)-

65. Chembl1872535

66. Dtxsid8035180

67. D,l-chrysanthemum Monocarboxylate

68. [(1s)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate

69. Hy-b1559

70. Nsc11782

71. Tox21_400074

72. D-allethrolone D-trans-chrysanthemate

73. Ent 16275

74. Ent 17510

75. Esbiol Concentrate 90% (salt/mix)

76. Mfcd00045443

77. Allethrin 100 Microg/ml In Methanol

78. Akos015900219

79. Allethrin 1000 Microg/ml In N-hexane

80. Ncgc00163953-01

81. Ncgc00163953-02

82. Ncgc00163953-04

83. Ncgc00164471-01

84. (3-allyl-2-methyl-4-oxo-cyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate

85. As-11751

86. Cas-584-79-2

87. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1r)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester. (1s.3s)-rel-

88. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester, [1r-[1.alpha.(s*),3.beta.]]-

89. Db-047389

90. Cs-0013441

91. Ft-0630540

92. Ft-0647652

93. Allethrin, Pestanal(r), Analytical Standard

94. Esbiothrin, Pestanal(r), Analytical Standard

95. D07530

96. Bioallethrin, Pestanal(r), Analytical Standard

97. 584a792

98. J-014709

99. Q1851694

100. W-105386

101. (.+-.)-allelrethonyl (.+-.)-cis,trans-chrysanthemate

102. (+)-trans-chrysanthemumic Acid Ester Of (.+-.)-allethrolone

103. Wln: L5v Butj B2u1 C1 Dov- Bl3tj A1 A1 C1uy1&1

104. 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one Ester Of 2,2-dimethyl-3-(2-methyl Propenyl) Cyclopropane Carboxylic Acid

105. 2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylate

106. 3-allyl-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, (1r-(1.alpha.(s*),3.beta.))-

107. 3-allyl-2-methyl-4-oxocyclopent-2-enyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate

108. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1r)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester, (1s,3s)-rel-

109. Cyclopropanecarboxylic Acid, 2,2-dimethyl-3-(2-methylpropenyl)-, Ester With 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one

110. Cyclopropanecarboxylic Acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester (va

111. Cyclopropanecarboxylic Acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl Ester, D-trans-

112. Cyclopropanecarboxylic Acid,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopentene-1-yl Ester

113. Cyclopropanecarboxylic Acid,2-dimethyl-3-(2-methylpropenyl)-, Ester With 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one

114. Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-,2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl Ester, (1r,3r)-

115. D-trans-allethrin, (s)-3-allyl-2-methyl-4-oxocyclopent-2-enyl-(1r,3r)-2,2-dimethyl-3-(2-methyl-prop-1-enyl)cyclopropancarboxylate

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 302.4 g/mol
Molecular Formula C19H26O3
XLogP34.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Exact Mass302.18819469 g/mol
Monoisotopic Mass302.18819469 g/mol
Topological Polar Surface Area43.4 Ų
Heavy Atom Count22
Formal Charge0
Complexity574
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Pyrethrins with piperonyl butoxide are used for topical treatment of pediculosis (lice infestations). Combinations of pyrethrins with piperonyl butoxide are not effective for treatment of scabies (mite infestations). Although there are no well-controlled comparative studies, many clinicians consider 1% lindane to be pediculicide of choice. However, some clinicians recommend use of pyrethrins with piperonyl butoxide, esp in infants, young children, & pregnant or lactating women ... . If used correctly, 1-3 treatments ... are usually 100% effective ... Oil based (eg, petroleum distillate) combinations ... produce the quickest results. ... For treatment of pediculosis, enough gel, shampoo, or solution ... should be applied to cover affected hair & adjacent areas ... After 10 min, hair is ... washed thoroughly ... treatment should be repeated after 7-10 days to kill any newly hatched lice. /Pyrethrins/

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3203


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)


5.2 Absorption, Distribution and Excretion

WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/

PMID:789062 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1475089 MIYAMOTO J; ENVIRON HEALTH PERSPECT 14: 15-28 (1976)


Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 2000.Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2000 (Plus Supplements)., p. 3203


Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/

U.S. Environmental Protection Agency/Office of Prevention, Pesticides, and Toxic Substances. Reigart, J.R., Roberts, J.R. Recognition and Management of Pesticide Poisonings. 5th ed. 1999. EPA Document No. EPA 735-R-98-003, and available in electronic format at: https://www.epa.gov/pesticides/safety/healthcare, p. 87


There were no major /metabolic/ differences between sexes, between low and high dose groups, nor between single-dose groups and repeated dose groups. The majority of radioactivity was eliminated within 3 days. Urinary elimination ranged from approximately 25 - 50% and fecal elimination ranged from 50 - 70%. There was no bioaccumulation of residue in tissues. ... /d-trans-Allethrin/

USEPA/OPPTS; Allethrins: Revised HED Chapter of Reregistration Eligibility Decision Document (RED). p.14 EPA -HQ-OPP-2006-0986-0012 (June 2007). Available from, as of June 9, 2008: https://www.regulations.gov/search/Regs/home.html#home


When allethrin labelled with (14)C in the acid moiety or with (3)H in the alcohol moiety was administered orally to male Sprague Dawley rats at levels ranging from 1 to 5 mg/kg body weight, the radiocarbon and tritium from the acid- and alcohol-labellings were eliminated in the urine (30% and 20.7%, respectively) and feces (29% and 27%, respectively) in 48 hr. ... Most of the metabolites excreted in the urine were ester-form metabolites together with two hydrolyzed products, chrysanthemum dicarboxylic acid (CDCA) and allethrolone. ...

WHO; Environ Health Criteria 87: ALLETHRINS - Allethrin - d-Allethrin - Bioallethrin - S-Bioallethrin (1989). Available from, as of June 10, 2008: https://www.inchem.org/documents/ehc/ehc/ehc87.htm


5.3 Metabolism/Metabolites

AFTER ADMINISTRATION OF LABELED ALLETHRIN TO MALE RATS, THE MAJOR METABOLITES FOUND WERE ALCOHOL-ACIDS. FROM NMR AND MASS SPECTRA A THIRD METABOLITE WAS IDENTIFIED AS ALLETHRIN WITH ONE CYCLOPROPANE METHYL HYDROXYLATED AND OXIDATION OF THE TRANSMETHYL TO A CARBOXYL GROUP. ...

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 307


/IN STUDYING THE METABOLISM OF ALLETHRIN IN HOUSEFLIES, IT WAS FOUND THAT IN/ ALLETHRIN LABELED IN THE KETOCYCLOPENTENYL PORTION OF THE MOLECULE, A METABOLITE THAT BEHAVED AS KETOCYCLOPENTENOL WAS ISOLATED BY PAPER CHROMATOGRAPHY. ... INVESTIGATORS USING ALLETHRIN LABELED IN CHRYSANTHEMUMIC ACID PORTION OF MOLECULE WERE ABLE TO DETECT ONLY TRACES OF ACID IN HOUSEFLY HOMOGENATES OR EXCRETA. ... ONLY TRACES OF UNCHANGED ALLETHRIN WERE RECOVERABLE AND THE BULK OF THE RECOVERED MATERIAL MUST BE A DERIVATIVE OF THE INTACT ESTER OR OF THE ACID.

White-Stevens, R. (ed.). Pesticides in the Environment: Volume 1, Part 1, Part 2. New York: Marcel Dekker, Inc., 1971., p. 218


Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone.

Aizawa, H. Metabolic Maps of Pesticides. New York, NY: Academic Press, 1982., p. 184


When allethrin was applied topically to houseflies, chromatography indicated the presence of allethrone and chrysanthemic acid in addition to allethrin and three unidentified compounds.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 470


For more Metabolism/Metabolites (Complete) data for ALLETHRINS (10 total), please visit the HSDB record page.


5.4 Mechanism of Action

Mode of Action: The allethrins are a type I pyrethroid (i.e., lacking a cyano group at the alpha carbon position of the alcohol moiety). The allethrins are axonic poisons that block the closing of the sodium gates in the nerves, and, thus, prolong the return of the membrane potential to its resting state leading to hyperactivity of the nervous system which can result in paralysis and/or death.

USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision for Allethrins p.5 EPA 738-R-07-001 (June 2007). Available from, as of June 7, 2008: https://www.epa.gov/pesticides/reregistration/status.htm


The mechanisms by which pyrethroids alone are toxic are complex and become more complicated when they are co-formulated with either piperonyl butoxide or an organophosphorus insecticide, or both, as these compounds inhibit pyrethroid metabolism. The main effects of pyrethroids are on sodium and chloride channels. Pyrethroids modify the gating characteristics of voltage-sensitive sodium channels to delay their closure. A protracted sodium influx (referred to as a sodium 'tail current') ensues which, if it is sufficiently large and/or long, lowers the action potential threshold and causes repetitive firing; this may be the mechanism causing paraesthesiae. At high pyrethroid concentrations, the sodium tail current may be sufficiently great to prevent further action potential generation and 'conduction block' ensues. Only low pyrethroid concentrations are necessary to modify sensory neurone function.

PMID:16180929 Bradberry SM et al; Toxicol Rev 24 (2): 93-106 (2005)


The interactions of natural pyrethrins and 9 pyrethroids with the nicotinic acetylcholine (ACh) receptor/channel complex of Torpedo electronic organ membranes were studied. None reduced (3)H-ACh binding to the receptor sites, but all inhibited (3)H-labeled perhydrohistrionicotoxin binding to the channel sites in presence of carbamylcholine. Allethrin inhibited binding noncompetitively, but (3)H-labeled imipramine binding competitively, suggesting that allethrin binds to the receptor's channel sites that bind imipramine. The pyrethroids were divided into 2 types according to their action: type A, which included allethrin, was more potent in inhibiting (3)H-H12-HTX binding and acted more rapidly. Type B, which included permethrin, was less potent and their potency increased slowly with time. The high affinities that several pyrethroids have for this nicotinic ACh receptor suggest that pyrethroids may have a synaptic site of action in addition to their well known effects on the axonal channels.

Abbassy MA et al; Pestic Biochem Physiol 19 (3): 299-308 (1983)


Phosphoinositide breakdown in guinea pig cerebral cortical synaptoneurosomes induced by the Type I pyrethroids allethrin, resmethrin, and permethrin and the Type II pyrethroid deltamethrin and fenvalerate were investigated with various receptor agonists as well as sodium channel blockers and agents. Phosphoinositide breakdown was determined from inositol-phosphate formation by tritiated inositol labeled synaptoneurosomes. All five pyrethroids dose dependently induced phosphoinositide breakdown. Type II pyrethroids exhibited higher potency and deltamethrin was more efficacious than the Type I pyrethroids. Five micromolar tetrodotoxin, a blocker of voltage dependent sodium channels, partially inhibited deltamethrin (85%) and fenvalerate (60%) responses but not allethrin or resmethrin. Fenvalerate induced stimulation of phosphoinositide breakdown was additive with stimulation elicited by the receptor agonists carbamylcholine (1 mM) and norepinephrine (1000 uM) but less than additive with the sodium channel agents batrachotoxin, pumiliotoxin-B, and scorpion venom. Allethrin (100 uM) was less than additive with receptor agonists or sodium channel agents and actually significantly inhibited response to scorpion venom. Effects for 100 uM allethrin with either fenvalerate or deltamethrin were not different from allethrin alone. Ten micromolar allethrin slightly decreased response to 10 to 100 uM deltamethrin. The local anesthetic dibucaine, a sodium channel activation inhibitor, completely blocked deltamethrin induced phosphoinositide breakdown but was much less effective in inhibiting allethrin response. It appears likely that Type-I pyrethroids induce phosphoinositide breakdown through a mechanism other than sodium channel activation while Type-II pyrethroids act in a manner analogous to other sodium channel agents.

PMID:2546657 Gusovsky F et al; Brain Research 492 (1/2): 72-8 (1989)


For more Mechanism of Action (Complete) data for ALLETHRINS (13 total), please visit the HSDB record page.


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