Rotenone

Names

[ CAS No. ]:
83-79-4

[ Name ]:
Rotenone

[Synonym ]:
(-)-rotenone
derris
(2R,6aS,12aS)-8,9-dimethoxy-2-(1-methylethenyl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
protax
(2R,6aS,12aS)-8,9-Dimethoxy-2-(prop-1-en-2-yl)-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Derris root
[2R-(2a,6aa,12aa)]-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
Rotacide E.C.
(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
MFCD09025614
5'-b-Rotenone
TUBATOXIN
(2R,6aS,12aS)-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
Foliafume E.C.
paraderil
Furo[2',3':7,8][1]benzopyrano[2,3-c][1]benzopyran-6(6aH)-one, 1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-, (2R,6aS,12aS)-
Dermostatin A
Rotenone,(2R,6aS,12aS)-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
(-)-cis-rotenone
[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)-
(2R,6aS,12aS)-2-Isopropenyl-8,9-dimethoxy-1,2,12,12a-tetrahydrochromeno[3,4-b]furo[2,3-h]chromen-6(6aH)-one
Noxfire
EINECS 201-501-9
Tubotoxine
Canex

Biological Activity

[Description]:

Rotenone is an mitochondrial electron transport chain complex I inhibitor.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Mitochondrial Metabolism

Research Areas >> Neurological Disease

[In Vitro]

Mitogen Activated Protein Kinase (MAPK), Toll-like receptor, Wnt, and Ras signaling pathways are intensively involved in the effect of rotenone on the ENS[2]. Rotenone-induced cell death is reduced by treatment as measured by decline in the levels of pro-apoptotic proteins. Moreover, treatment significantly augments the levels of anti-apoptotic Bcl2 and blocks the release of cytochrome c, thereby alleviating the rotenone-induced dopaminergic neuronal loss, as evidenced by tyrosine hydroxylase (TH) immunostaining in the striatum[3].

[In Vivo]

Rotenone causes a significant increase in the excitatory amino acid neurotransmitters; glutamate and aspartate together with a significant decrease in the inhibitory amino acids, GABA, glycine and taurine are observed in the cerebellum of rat model of PD[1]. Rotenone (1.5, 2, or 2.5 mg/kg) causes a dose-dependent increase in α-synuclein in the substantia nigra. Furthermore, at 2 and 2.5 mg/kg, rotenone causes a significant decrease in the number of tyrosine hydroxylase-immunoreactive neurons in the substantia nigra, and dopamine in the striatum in rats[4].

[References]

[1]. Khadrawy YA, et al. Cerebellar neurochemical and histopathological changes in rat model of Parkinson's disease induced by intrastriatal injection of rotenone. Gen Physiol Biophys. 2016 Nov 30

[2]. Guan Q, et al. RNA-Seq Expression Analysis of Enteric Neuron Cells with Rotenone Treatment and Prediction of Regulated Pathways. Neurochem Res. 2016 Nov 30

[3]. Kishore Kumar SN, et al. Morinda citrifolia mitigates rotenone-induced striatal neuronal loss in male Sprague-Dawley rats by preventing mitochondrial pathway of intrinsic apoptosis. Redox Rep. 2016 Nov 24:1-12

[4]. Zhang ZN, et al. Subcutaneous rotenone rat model of Parkinson's disease: dose exploration study. Brain Res. 2016 Nov 19. pii: S0006-8993(16)30776-4

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
559.8±50.0 °C at 760 mmHg

[ Melting Point ]:
159-164 °C(lit.)

[ Molecular Formula ]:
C₂₃H₂₂O₆

[ Molecular Weight ]:
394.417

[ Flash Point ]:
244.6±30.2 °C

[ Exact Mass ]:
394.141632

[ PSA ]:
63.22000

[ LogP ]:
4.65

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.591

[ Stability ]:
Stable, but light and air sensitive. Combustible. Incompatible with oxidizing agents, especially in the presence of alkalies.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DJ2800000

CHEMICAL NAME :: (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-

CAS REGISTRY NUMBER :: 83-79-4

LAST UPDATED :: 199803

DATA ITEMS CITED :: 71

MOLECULAR FORMULA :: C23-H22-O6

MOLECULAR WEIGHT :: 394.45

WISWESSER LINE NOTATION :: T G5 D6 B666 CV HO MO POT&TT&J IY1&U1 SO1 TO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration into the eye

SPECIES OBSERVED :: Rodent - rabbit

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 143 mg/kg

TOXIC EFFECTS :: Gastrointestinal - other changes

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 294 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LCLo - Lowest published lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 500 mg/m3/30M

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >940 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - coma Cardiac - pulse rate increase, without fall in BP

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 200 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - coma Cardiac - pulse rate increase, without fall in BP

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 132 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2650 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 650 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 650 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from stomach Gastrointestinal - hypermotility, diarrhea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 350 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Behavioral - muscle contraction or spasticity Lungs, Thorax, or Respiration - respiratory stimulation

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - pig

DOSE/DURATION :: 3700 ug/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Gastrointestinal - ulceration or bleeding from stomach

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Bird - pigeon

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - duck

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1505 mg/kg/14D-C

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5460 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in bone marrow (not otherwise specified) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 54600 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 180 mg/kg/9D-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - chronic pulmonary edema Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3245 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 71 mg/kg/42D-I

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 68 mg/kg/40D-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3285 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - thyroid tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 50 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2960 ug/kg

SEX/DURATION :: female 6-9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 98 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth)

MUTATION DATA

TYPE OF TEST :: Sex chromosome loss and nondisjunction

TEST SYSTEM :: Rodent - hamster Lung

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 263,173,1991 *** REVIEWS *** ACGIH TLV-Not classifiable as a human carcinogen DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-TWA 5 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 TOXICOLOGY REVIEW CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,1171,1976 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 MSHA STANDARD-air:TWA 5 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: 3,224,1971 OSHA PEL (Gen Indu):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1910.1000,1994 OSHA PEL (Construc):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1926.55,1994 OSHA PEL (Shipyard):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 29,1915.1000,1993 OSHA PEL (Fed Cont):8H TWA 5 mg/m3 CFRGBR Code of Federal Regulations. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) Volume(issue)/page/year: 41,50-204.50,1994 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 5 mg/m3 JAN 1993 OEL-BELGIUM:TWA 5 mg/m3 JAN 1993 OEL-DENMARK:TWA 5 mg/m3 JAN 1993 OEL-FINLAND:TWA 5 mg/m3;STEL 10 mg/m3 JAN 1993 OEL-GERMANY:TWA 5 mg/m3 JAN 1993 OEL-THE NETHERLANDS:TWA 5 mg/m3 JAN 1993 OEL-THE PHILIPPINES:TWA 5 mg/m3 JAN 1993 OEL-SWITZERLAND:TWA 5 mg/m3 JAN 1993 OEL-TURKEY:TWA 5 mg/m3 JAN 1993 OEL-UNITED KINGDOM:TWA 5 mg/m3;STEL 10 mg/m3 JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO ROTENONE-air:10H TWA 5 mg/m3 REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992 NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 67530 No. of Facilities: 70 (estimated) No. of Industries: 3 No. of Occupations: 4 No. of Employees: 2937 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 67530 No. of Facilities: 913 (estimated) No. of Industries: 3 No. of Occupations: 3 No. of Employees: 8100 (estimated) No. of Female Employees: 2470 (estimated)

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H315-H319-H335-H410

[ Precautionary Statements ]:
P273-P280-P301 + P310 + P330-P337 + P313-P391-P501

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R25;R36/37/38;R50/53

[ Safety Phrases ]:
22-24/25-36-45-60-61

[ RIDADR ]:
UN 2811 6.1/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
DJ2800000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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Related Compounds

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