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(-)-cis-rotenone
dactinol

Supplier Sponsors

Name:(1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
CAS Number: 83-79-4Picture of molecule3D/inchi
Other(deleted CASRN):12679-58-2
ECHA EINECS - REACH Pre-Reg:201-501-9
FDA UNII: 03L9OT429T
Nikkaji Web:J108.000H
Beilstein Number:6773081
MDL:MFCD09025614
XlogP3:4.10 (est)
Molecular Weight:394.42354000
Formula:C23 H22 O6
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Appearance:colorless to brownish crystals (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.2 mg/L @ 20 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Rotenone 98%
BOC Sciences
For experimental / research use only.
Rotenone 98+%
Glentham Life Sciences
Rotenone
Shaanxi Y-Herb Biotechnology
White Derris Root Extract Bio Insecticide Pesticide Rotenone Powder CAS 83-79-4
Sigma-Aldrich
For experimental / research use only.
Rotenone PESTANAL®, analytical standard
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-cat LDLo 650 ug/kg
GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

intravenous-dog LDLo 650 ug/kg
BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

oral-dog LDLo 300 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

oral-duck LD50 > 2000 mg/kg
Down to Earth. Vol. 35, Pg. 25, 1979.

oral-frog LDLo 4 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

intraperitoneal-guinea pig LDLo 10 mg/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.

oral-guinea pig LDLo 100 mg/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.

oral-human LDLo 143 mg/kg
GASTROINTESTINAL: OTHER CHANGES
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.

unreported-man LDLo 294 mg/kg
"Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.

intraperitoneal-mouse LD50 2650 ug/kg
Radiation Research. Vol. 91, Pg. 186, 1982.

oral-mouse LD50 2800 ug/kg
EHP, Environmental Health Perspectives. Vol. 14, Pg. 109, 1976.

intramuscular-rabbit LDLo 5 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

intravenous-rabbit LDLo 350 ug/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.

oral-rabbit LDLo 1600 mg/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

intraperitoneal-rat LD50 1600 ug/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.

intravenous-rat LD50 200 ug/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.

oral-rat LD50 60 mg/kg
Down to Earth. Vol. 35, Pg. 25, 1979.

unreported-rat LD50 132 mg/kg
Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes. Vol. 15, Pg. 929, 1980.

Dermal Toxicity:
skin-rabbit LD50 > 1000 mg/kg
Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 5, 1978.

subcutaneous-rabbit LDLo 20 mg/kg
Journal of Pharmacology and Experimental Therapeutics. Vol. 43, Pg. 193, 1931.

skin-rat LD50 > 940 mg/kg
World Review of Pest Control. Vol. 9, Pg. 119, 1970.

Inhalation Toxicity:
inhalation-rat LCLo 500 mg/m3/30M
Farmaco, Edizione Scientifica. Vol. 20, Pg. 270, 1965.
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (-)-cis-rotenone usage levels up to:
 not for fragrance use.
 
Recommendation for (-)-cis-rotenone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
EPA-Iris:IRIS
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6758
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
Chemidplus:0000083794
EPA/NOAA CAMEO:hazardous materials
RTECS:83-79-4
 
References:
 (1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:83-79-4
Pubchem (cid):6758
Pubchem (cas):83-79-4
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C07593
HMDB (The Human Metabolome Database):HMDB34436
FooDB:FDB012837
Export Tariff Code:2932.90.4100
VCF-Online:VCF Volatile Compounds in Food
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 bean yam bean
Search Trop Picture
 lonchocarpus spp
Search Trop Picture
 
Synonyms:
 barbasco
 cenol garden dust
 chem-fish synergized
 dactinol
(1S,6R,13S)-16,17-dimethoxy-6-prop-1-en-2-yl-2,7,20-trioxapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-3(11),4(8),9,14,16,18-hexaen-12-one
 protax
(-)-rotenone
(2R-(2alpha,6aalpha,12aalpha))-1,2,12,12a-tetrahydro-8,9-dimethoxy-2-(1-methyl ethenyl)(1)benzopyrano(3,4-b)furo(2,3-H)benzopyran-6(6aH)-one
 

Articles:

Info:Rotenone
PubMed:Asiatic acid nullified aluminium toxicity in in vitro model of Alzheimer's disease.
PubMed:Isolongifolene attenuates rotenone-induced mitochondrial dysfunction, oxidative stress and apoptosis.
PubMed:In Vitro Evaluation of Mitochondrial Function and Estrogen Signaling in Cell Lines Exposed to the Antiseptic Cetylpyridinium Chloride.
PubMed:Ginsenosides Rd and Re co-treatments improve rotenone-induced oxidative stress and mitochondrial impairment in SH-SY5Y neuroblastoma cells.
PubMed:Agaricus blazei extract abrogates rotenone-induced dopamine depletion and motor deficits by its anti-oxidative and anti-inflammatory properties in Parkinsonic mice.
PubMed:Azilsartan ameliorates apoptosis of dopaminergic neurons and rescues characteristic parkinsonian behaviors in a rat model of Parkinson's disease.
PubMed:Cytoprotective action against oxidative stress in astrocytes and neurons by Bactris guineensis (L.) H.E. Moore (corozo) fruit extracts.
PubMed:Neuroprotective effect of Demethoxycurcumin, a natural derivative of Curcumin on rotenone induced neurotoxicity in SH-SY 5Y Neuroblastoma cells.
PubMed:Cyclodextrin-based miniaturized solid phase extraction for biopesticides analysis in water and vegetable juices samples analyzed by ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry.
PubMed:Lumbee traditional medicine: Neuroprotective activities of medicinal plants used to treat Parkinson's disease-related symptoms.
PubMed:Agaricus blazei extract attenuates rotenone-induced apoptosis through its mitochondrial protective and antioxidant properties in SH-SY5Y neuroblastoma cells.
PubMed:Neuroprotective Effects of Germinated Brown Rice in Rotenone-Induced Parkinson's-Like Disease Rats.
PubMed:AdipoR-increased intracellular ROS promotes cPLA2 and COX-2 expressions via activation of PKC and p300 in adiponectin-stimulated human alveolar type II cells.
PubMed:Acute and subacute toxicity studies of CMICE-013, a novel iodinated rotenone-based myocardial perfusion tracer, in Sprague Dawley rats and Gottingen minipigs.
PubMed:Vanillin Attenuated Behavioural Impairments, Neurochemical Deficts, Oxidative Stress and Apoptosis Against Rotenone Induced Rat Model of Parkinson's Disease.
PubMed:Identification of chemicals that mimic transcriptional changes associated with autism, brain aging and neurodegeneration.
PubMed:Neuroprotective effect of asiatic acid on rotenone-induced mitochondrial dysfunction and oxidative stress-mediated apoptosis in differentiated SH-SYS5Y cells.
PubMed:Evidence of neuroprotective effects of saffron and crocin in a Drosophila model of parkinsonism.
PubMed:Amelioration of apoptotic events in the skeletal muscle of intra-nigrally rotenone-infused Parkinsonian rats by Morinda citrifolia--up-regulation of Bcl-2 and blockage of cytochrome c release.
PubMed:Neurosupportive Role of Vanillin, a Natural Phenolic Compound, on Rotenone Induced Neurotoxicity in SH-SY5Y Neuroblastoma Cells.
PubMed:S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress.
PubMed:Some Operational Characteristics of Glycine Release in Rat Retina: The Role of Reverse Mode Operation of Glycine Transporter Type-1 (GlyT-1) in Ischemic Conditions.
PubMed:Environment-contact administration of rotenone: A new rodent model of Parkinson's disease.
PubMed:Novel Radiolytic Rotenone Derivative, Rotenoisin B with Potent Anti-Carcinogenic Activity in Hepatic Cancer Cells.
PubMed:Microglial HO-1 induction by curcumin provides antioxidant, antineuroinflammatory, and glioprotective effects.
PubMed:Aqueous extract of tomato seeds attenuates rotenone-induced oxidative stress and neurotoxicity in Drosophila melanogaster.
PubMed:Standardized extract of Withania somnifera (Ashwagandha) markedly offsets rotenone-induced locomotor deficits, oxidative impairments and neurotoxicity in Drosophila melanogaster.
PubMed:Combined oral supplementation of fish oil and quercetin enhances neuroprotection in a chronic rotenone rat model: relevance to Parkinson's disease.
PubMed:A new Drosophila model to study the interaction between genetic and environmental factors in Parkinson's disease.
PubMed:Oral supplements of aqueous extract of tomato seeds alleviate motor abnormality, oxidative impairments and neurotoxicity induced by rotenone in mice: relevance to Parkinson's disease.
PubMed:Synthesis of rotenone-O-monosaccharide derivatives and their phloem mobility.
PubMed:Neuroprotective effects of anthocyanin- and proanthocyanidin-rich extracts in cellular models of Parkinson׳s disease.
PubMed:The function of glycine decarboxylase complex is optimized to maintain high photorespiratory flux via buffering of its reaction products.
PubMed:Toxicological evaluation of a rotenone derivative in rodents for clinical myocardial perfusion imaging.
PubMed:Cytotoxic constituents of Pachyrhizus tuberosus from Peruvian amazon.
PubMed:Degradation of rotenone in yam bean seeds ( Pachyrhizus sp.) through food processing.
PubMed:Horizontal transfer of diatomaceous earth and botanical insecticides in the common bed bug, Cimex lectularius L.; hemiptera: cimicidae.
PubMed:[Rapid screening and confirmation of 281 pesticide residues in apples, tomatos and cabbages by liquid chromatography/ quadrupole time-of-flight mass spectrometry].
PubMed:Neuroprotective effect of aqueous extract of Selaginella delicatula as evidenced by abrogation of rotenone-induced motor deficits, oxidative dysfunctions, and neurotoxicity in mice.
PubMed:Dissipation and residue of rotenone in cabbage and soil under field conditions.
PubMed:Deguelin action involves c-Met and EGFR signaling pathways in triple negative breast cancer cells.
PubMed:Polyphenols protect the epithelial barrier function of Caco-2 cells exposed to indomethacin through the modulation of occludin and zonula occludens-1 expression.
PubMed:LC/MS characterization of rotenone induced cardiolipin oxidation in human lymphocytes: implications for mitochondrial dysfunction associated with Parkinson's disease.
PubMed:Valeriana officinalis attenuates the rotenone-induced toxicity in Drosophila melanogaster.
PubMed:Sodium butyrate improves locomotor impairment and early mortality in a rotenone-induced Drosophila model of Parkinson's disease.
PubMed:Consumer and farmer safety evaluation of application of botanical pesticides in black pepper crop protection.
PubMed:Effect of Withania somnifera supplementation on rotenone-induced oxidative damage in cerebellum and striatum of the male mice brain.
PubMed:Highly variable insect control efficacy of Tephrosia vogelii chemotypes.
PubMed:Follicular fluid supplementation during in vitro maturation promotes sperm penetration in bovine oocytes by enhancing cumulus expansion and increasing mitochondrial activity in oocytes.
PubMed:Propensity of Selaginella delicatula aqueous extract to offset rotenone-induced oxidative dysfunctions and neurotoxicity in Drosophila melanogaster: Implications for Parkinson's disease.
PubMed:Oxygen consumption rate of permeabilized cells and isolated mitochondria from pork M. masseter and liver examined fresh and after freeze-thawing at different pH values.
PubMed:Molecular aspects of dopaminergic neurodegeneration: gene-environment interaction in parkin dysfunction.
PubMed:Fish oil prophylaxis attenuates rotenone-induced oxidative impairments and mitochondrial dysfunctions in rat brain.
PubMed:Differential protective effects of quercetin, resveratrol, rutin and epigallocatechin gallate against mitochondrial dysfunction induced by indomethacin in Caco-2 cells.
PubMed:Bacopa monnieri extract offsets rotenone-induced cytotoxicity in dopaminergic cells and oxidative impairments in mice brain.
PubMed:Flavanones and rotenoids from the roots of Amorpha fruticosa L. that inhibit bacterial neuraminidase.
PubMed:Microplate-based kinetic method for assay of mitochondrial NADH-- and succinate--cytochrome c reductase activities.
PubMed:[Separation and preparation of two rotenoids from the roots of Derris by high-speed counter-current chromatography].
PubMed:Detoxified extract of Rhus verniciflua stokes inhibits rotenone-induced apoptosis in human dopaminergic cells, SH-SY5Y.
PubMed:Attenuation of rotenone-induced mitochondrial oxidative damage and neurotoxicty in Drosophila melanogaster supplemented with creatine.
PubMed:Molecular mechanisms of methylmercury-induced cell death in human HepG2 cells.
PubMed:Lipofuscin-bound iron is a major intracellular source of oxidants: role in senescent cells.
PubMed:Development and evaluation of granule and emulsifiable concentrate formulations containing Derris elliptica extract for crop pest control.
PubMed:Triacylglycerol-induced impairment in mitochondrial biogenesis and function in J774.2 and mouse peritoneal macrophage foam cells.
PubMed:Neuroprotective efficacy of Bacopa monnieri against rotenone induced oxidative stress and neurotoxicity in Drosophila melanogaster.
PubMed:Residues of rotenone, azadirachtin, pyrethrins and copper used to control Bactrocera oleae (Gmel.) in organic olives and oil.
PubMed:Rapid analysis of organic farming insecticides in soil and produce using ultra-performance liquid chromatography/tandem mass spectrometry.
PubMed:Delayed gastric emptying and enteric nervous system dysfunction in the rotenone model of Parkinson's disease.
PubMed:Effects of lactate on beef heart mitochondrial oxygen consumption and muscle darkening.
PubMed:Tumor promoting and co-carcinogenic effects in medium-term rat hepatocarcinogenesis are not modified by co-administration of 12 pesticides in mixture at acceptable daily intake.
PubMed:Persistence and effects of rotenone on oil quality in two Italian olive cultivars.
PubMed:Degradation and persistence of rotenone in soils and influence of temperature variations.
PubMed:Backbone cyclised peptides from plants show molluscicidal activity against the rice pest Pomacea canaliculata (golden apple snail).
PubMed:Photodegradation of rotenone in soils under environmental conditions.
PubMed:Acute and sublethal toxicities of rotenone in juvenile rainbow trout (Oncorhynchus mykiss): swimming performance and oxygen consumption.
PubMed:Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world.
PubMed:Fast and versatile multiresidue method for the analysis of botanical insecticides on fruits and vegetables by HPLC/DAD/MS.
PubMed:Fat intake reverses the beneficial effects of low caloric intake on skeletal muscle mitochondrial H(2)O(2) production.
PubMed:Triacylglycerol-mediated oxidative stress inhibits nitric oxide production in rat isolated hepatocytes.
PubMed:Larvicidal and adulticidal activity of alkylphthalide derivatives from rhizome of Cnidium officinale against Drosophila melanogaster.
PubMed:Mitochondrial reduction of metmyoglobin: dependence on the electron transport chain.
PubMed:Comment on cubé resin insecticide: identification and biological activity of 29 rotenoid constituents.
PubMed:Mechanism underlying oxidative stress-mediated lipotoxicity: exposure of J774.2 macrophages to triacylglycerols facilitates mitochondrial reactive oxygen species production and cellular necrosis.
PubMed:Rotenone, a mitochondrial electron transport inhibitor, ameliorates ischemia-reperfusion-induced intestinal mucosal damage in rats.
PubMed:Pesticides and organic agriculture.
PubMed:Evaluation of calcium-alginate gel as an artificial diet medium for bioassays on common cutworms.
PubMed:Insecticidal effect of phthalides and furanocoumarins from Angelica acutiloba against Drosophila melanogaster.
PubMed:Effect of the epicuticular waxes of fruits and vegetables on the photodegradation of rotenone.
PubMed:Rotenone and rotenoids in cubè resins, formulations, and residues on olives.
PubMed:Redox signaling in the growth and development of colonial hydroids.
PubMed:Alpha-lipoic acid inhibits glycogen synthesis in rat soleus muscle via its oxidative activity and the uncoupling of mitochondria.
PubMed:Rotenone residues on olives and in olive oil.
PubMed:Mitochondrial control of inducible nitric oxide production in stimulated RAW 264.7 macrophages.
PubMed:Rats and risk.
PubMed:Determination of whole-body rotenone residues in the brown tree snake (Boiga irregularis).
PubMed:Cubé resin insecticide: identification and biological activity of 29 rotenoid constituents.
PubMed:Isolation of a novel NAD(P)H-quinone oxidoreductase from the cyanobacterium Synechocystis PCC6803.
PubMed:Mechanism of p-hydroxybenzoate ester-induced mitochondrial dysfunction and cytotoxicity in isolated rat hepatocytes.
PubMed:Properties of the respiratory NAD(P)H dehydrogenase isolated from the cyanobacterium Synechocystis PCC6803.
PubMed:Rates of mitochondrial and peroxisomal beta-oxidation of palmitate change during postnatal development and food deprivation in liver, kidney and heart of pigs.
PubMed:Mitochondrial NADH dehydrogenase activity and ability to tolerate acetaldehyde determine faster ethanol production in Saccharomyces cerevisiae.
PubMed:An investigation of dye reduction by food-borne bacteria.
PubMed:Effects of 2(3)-tert-butyl-4-hydroxyanisole (BHA) on in situ mitochondria of Trypanosoma cruzi.
PubMed:Decrease of phosphorylating oxidation and increase of heat producing NADH oxidation in rat liver mitochondria during life-span prolongation of rats by calorie-restricted diet.
PubMed:Respiratory activity in Listeria monocytogenes.
PubMed:Partial purification and properties of the assimilatory nitrate reductase of the food yeast Candida utilis.
PubMed:The contribution of hepatic metabolism to diet-induced thermogenesis.
PubMed:Carcinogenesis with the insecticide rotenone.
PubMed:Residues of rotenone and rotenolone on lettuce and tomato fruit after treatment in the field with rotenone formulations.
PubMed:Modification of mitochondrial respiration by aging and dietary restriction.
PubMed:A specific method for the assay of select chlorinated pesticides.
PubMed:Distribution of rotenone and deguelin in Tephrosia vogelii and separation of rotenoid-rich fractions.
PubMed:[Round table discussion on mycotoxins].
PubMed:The detection of acute toxicity with Daphnia magna.
 
Notes:
Widely distrib. in the Leguminosae (Papilionoideae) e.g. Pachyrrhizus erosus (yam bean) Rotenone is an odorless chemical that is used as a broad-spectrum insecticide, piscicide, and pesticide. It occurs naturally in the roots and stems of several plants such as the jicama vine plant. In mammals, including humans, it is linked to the development of Parkinson's disease. (Wikipedia)
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