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Substance Name: Rotenone [BSI:ISO]
RN: 83-79-4
UNII: 03L9OT429T
InChIKey: JUVIOZPCNVVQFO-HBGVWJBISA-N

Note

  • A botanical insecticide that is an inhibitor of mitochondrial electron transport.

Molecular Formula

  • C23-H22-O6

Molecular Weight

  • 394.4208
 

Classification Codes

Classification Codes

  • Acaricide
  • Agricultural Chemical
  • Enzyme Inhibitors
  • Human Data
  • Insecticide
  • Insecticides
  • Mutation Data
  • Natural Product
  • Pesticides
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data
  • Uncoupling Agents

Superlist Classification Codes

  • TWA 5 mg/m3
  • TWA 5 mg/m3; Not classifiable as a human carcinogen

Names and Synonyms

Results Name

  • Rotenone [BSI:ISO]

Name of Substance

  • Rotenone
  • Rotenone [BSI:ISO]

MeSH Heading

  • Rotenone

Synonyms

  • (-)-cis-Rotenone
  • (-)-Rotenone
  • (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-2-alpha-isopropenyl-8,9-dimethoxy-
  • (2R-(2alpha,6aalpha,12aalpha))-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)(1)benzopyrano(3,4-b)furo(2,3-h)benzopyran-6(6aH)-one
  • (2R-(6aalpha,12aalpha)-1,2-Dihydro-2-isopropenyl-8,9-dimethoxychromano(3,4-b)furo(2,3-h)chroman-6-on
  • 1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one
  • 1,2,12,12aalpha-Tetrahydro-2a-isopropenyl-8,9-dimethoxy(1)benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one
  • 5'-beta-Rotenone
  • AI3-00133
  • Barbasco
  • Canex
  • Caswell No. 725
  • CCRIS 895
  • Cenol garden dust
  • Chem fish
  • Chem-Fish Synergized
  • Chem-Mite
  • Cube extract
  • Cube root
  • Cube-Pulver
  • Cubor
  • Curex flea duster
  • Dactinol
  • Deril
  • Derrin
  • Derris
  • Derris (insecticide)
  • Derris root
  • Dri-Kil
  • EINECS 201-501-9
  • ENT 133
  • EPA Pesticide Chemical Code 071003
  • Extrax
  • Fish-Tox
  • Foliafume E.C.
  • Gerane
  • Green cross warble powder
  • Haiari
  • HSDB 1762
  • Liquid derris
  • Mexide
  • NCI-C55210
  • Nekoe
  • Nicouline
  • Noxfire
  • Noxfish
  • NSC 26258
  • Nusyn-noxfish
  • Paraderil
  • Pb-Nox
  • Powder and root
  • Prenfish
  • Prentox
  • Prentox Synpren-Fish
  • Pro-Nox fish
  • Ro-KO
  • Ronone
  • Rotacide E.C.
  • Rotefive
  • Rotefour
  • Rotenon
  • Rotenona
  • Rotenona [Spanish]
  • Rotenone
  • Rotenox
  • Rotenox 5EC
  • Rotessenol
  • Rotocide
  • Synpren
  • Tubatoxin
  • UNII-03L9OT429T

Systematic Names

  • (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-
  • (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R-(2alpha,6aalpha,12aalpha))-
  • (2R,6aS,12aS)-1,2,6,6a,12,12a-hexahydro-2-isopropenyl-8,9-dimethoxychromeno(3,4-b)furo(2,3-h)chromen-6-one
  • Rotenone

Superlist Names

  • (1)Benzopyrano(3,4-b)furo(2,3-h)(1)benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R-(2alpha,6aalpha,12aalpha))-
  • Barbasco
  • Rotenone
  • Rotenone, commercial

Registry Numbers

CAS Registry Number

  • 83-79-4

FDA UNII

  • 03L9OT429T

Other Registry Number

  • 12679-58-2

System Generated Number

  • 0000083794

Structure Descriptors

InChI

1S/C23H22O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,16,20-21H,1,8,10H2,2-4H3/t16-,20-,21+/m1/s1

InChIKey

JUVIOZPCNVVQFO-HBGVWJBISA-N

Smiles

c12c3c(O[C@H](C3)C(=C)C)ccc1C(=O)[C@@H]1[C@H](O2)COc2c1cc(c(c2)OC)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 650ug/kg (0.65mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog LDLo intravenous 650ug/kg (0.65mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
dog LDLo oral 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
duck LD50 oral > 2gm/kg (2000mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
frog LDLo oral 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
guinea pig LDLo intraperitoneal 10mg/kg (10mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
guinea pig LDLo oral 100mg/kg (100mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH

LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA
Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 135, 1936.
human LDLo oral 143mg/kg (143mg/kg) GASTROINTESTINAL: OTHER CHANGES "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.
man LDLo unreported 294mg/kg (294mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 2650ug/kg (2.65mg/kg)   Radiation Research. Vol. 91, Pg. 186, 1982.
mouse LD50 oral 2800ug/kg (2.8mg/kg)   EHP, Environmental Health Perspectives. Vol. 14, Pg. 109, 1976.
pig LDLo oral 3700ug/kg (3.7mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of the American Veterinary Medical Association. Vol. 130, Pg. 410, 1957.
pigeon LDLo intravenous 1mg/kg (1mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LD50 skin > 1gm/kg (1000mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 5, 1978.
rabbit LDLo intramuscular 5mg/kg (5mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo intravenous 350ug/kg (0.35mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo oral 1600mg/kg (1600mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.
rat LCLo inhalation 500mg/m3/30M (500mg/m3)   Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 intraperitoneal 1600ug/kg (1.6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 intravenous 200ug/kg (0.2mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
rat LD50 oral 60mg/kg (60mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
rat LD50 skin > 940mg/kg (940mg/kg)   World Review of Pest Control. Vol. 9, Pg. 119, 1970.
rat LD50 unreported 132mg/kg (132mg/kg)   Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 15, Pg. 929, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 176 deg C   EXP
log P (octanol-water) 4.1 (none)   EXP
Water Solubility 0.2 mg/L 20 EXP
Henry's Law Constant 1.12E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.29E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.