Cannabis Compound Database: Showing Compound Card for Permethrin (CDB006194)

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Record Information

Version

1.0

Created at

2020-07-28 20:15:00 UTC

Updated at

2020-12-07 19:12:20 UTC

CannabisDB ID

CDB006194

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Permethrin

Description

Permethrin, also known as elimite or ambush, belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group. Based on a literature review a significant number of articles have been published on Permethrin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate	ChEBI
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylic acid, (3-phenoxyphenyl) methyl ester	ChEBI
Elimite	Kegg
(3-Phenoxyphenyl)methyl (+-)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid	Generator
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropane carboxylate, (3-phenoxyphenyl) methyl ester	Generator
(m-Phenoxybenzyl)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
3-Phenoxybenzyl-(+-)-cis,trans-2,2-dichlorovinyl-2,2-dimethyl-cyclopropylcarboxylic acid, ester	MeSH
3-Phenoxybenzyl-cis,trans-(1Rs)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate	MeSH
Ambush	MeSH
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester	MeSH
NRDC 143	MeSH
NRDC 147	MeSH
NRDC-143	MeSH
NRDC-147	MeSH
NRDC143	MeSH
NRDC147	MeSH
Nittifor	MeSH
Permethrin, (1R-cis)-isomer	MeSH
Permethrin, (1R-trans)-isomer	MeSH
Permethrin, (1S-cis)-isomer	MeSH
Permethrin, (1S-trans)-isomer	MeSH
Permethrin, (cis)-isomer	MeSH
Permethrin, (cis-(+-))-isomer	MeSH
Permethrin, (trans)-isomer	MeSH
Permethrin, (trans-(+-))-isomer	MeSH
Permethrin, trans-(1Rs)-isomer	MeSH
cis Permethrin	MeSH
cis-(1Rs)-Permethrin	MeSH
cis-Permethrin	MeSH
Permethrin, cis-(1Rs)-isomer	MeSH
trans Permethrin	MeSH
trans-(1Rs)-Permethrin	MeSH
trans-Permethrin	MeSH

Chemical Formula

C₂₁H₂₀Cl₂O₃

Average Molecular Weight

391.288

Monoisotopic Molecular Weight

390.07894992

IUPAC Name

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Traditional Name

permethrin

CAS Registry Number

Not Available

SMILES

CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC(OC2=CC=CC=C2)=CC=C1

InChI Identifier

InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

InChI Key

RLLPVAHGXHCWKJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Pyrethroids

Alternative Parents

Substituents

Pyrethroid skeleton
Diphenylether
Diaryl ether
Benzyloxycarbonyl
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Cyclopropanecarboxylic acid or derivatives
Benzenoid
Carboxylic acid ester
Ketene acetal or derivatives
Carboxylic acid derivative
Chloroalkene
Haloalkene
Ether
Vinyl halide
Monocarboxylic acid or derivatives
Vinyl chloride
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organohalogen compound
Organochloride
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cyclopropanes (CHEBI:34911 )
cyclopropanecarboxylate ester (CHEBI:34911 )
a monoterpenoid (CPD-13115 )

Ontology

Coma

Vascular disorders:

Hypotension

General disorders and administration site conditions:

Pain

Respiratory, thoracic and mediastinal disorders:

Cough

Gastrointestinal disorders:

Nervous system disorders:

Tremor

Ingestion

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Household products:

Pesticide:

Insecticide

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.24	ALOGPS
logP	5.7	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	114.28 m³·mol⁻¹	ChemAxon
Polarizability	39.43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-3900000000-469dc103f8f391a6bb7f	Spectrum
Predicted GC-MS	Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Permethrin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-956860faa94e3dea2ee2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-ce2901f0a3049806d95f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-b5846ca870454df7f44f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-0900000000-474995c2ccb155f0975c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-1900000000-261c3708f1e50c4a8418	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-006t-2900000000-4915b2e2cee108c117a2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0002-0900000000-a73154cdccdc124955c0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0002-1900000000-2f9800db80661116530a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0002-1900000000-bf65bfc29edf7e8f72d6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0002-1900000000-91cb4c87ae286d88f203	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-0002-1900000000-2546d86434c241ad989e	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0519000000-0f6eb9a687fe3c0d66c4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-1923000000-a400c6833ac566d7a622	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-2900000000-7758be41aece58f5d5d1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0109000000-fdac422c546f05b83ceb	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1709000000-f755eb7d0bee859d0bb8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9500000000-97e9860533a91746241d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0536-0429000000-98939aa3532b9312d6ac	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2923000000-0cd57653df5af5d7ac42	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001l-8911000000-9f85adb3775c89af21a5	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0119000000-eda907ff628cd2b35844	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ki-1902000000-84bc834f9310543ce7d7	2021-10-11	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9211000000-bcaffb823cfb3efededa	2021-10-11	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0250296

DrugBank ID

DB04930

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

36845

KEGG Compound ID

C14388

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Permethrin

METLIN ID

Not Available

PubChem Compound

40326

PDB ID

Not Available

ChEBI ID

34911

References

General References

Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]

Showing Compound Card for Permethrin (CDB006194)

Structure for CDB006194 (Permethrin)