Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H5NS |
Molecular Weight | 99.154 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CCN=C=S
InChI
InChIKey=ZOJBYZNEUISWFT-UHFFFAOYSA-N
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Molecular Formula | C4H5NS |
Molecular Weight | 99.154 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Allyl isothiocyanate (AITC), also known as mustard oil, is one of the most common naturally occurring isothiocyanates, which occurs in many common cruciferous vegetables. Besides antimicrobial activity against a wide spectrum of pathogens, it showed anticancer activity in both cultured cancer cells and animal models, although the underlining mechanisms remain largely undefined. Allyl isothiocyanate is a TRPA1 and TRPV1 agonist and pungency and lachrymatory effects of Allyl isothiocyanate are mediated through the TRPA1 and TRPV1 ion channels. Allyl isothiocyanate irritates the mucous membranes and induces eczematous or vesicular skin reactions.
Approval Year
Doses
Dose | Population | Adverse events |
---|---|---|
0.05 % 1 times / day single, topical Studied dose Dose: 0.05 %, 1 times / day Route: topical Route: single Dose: 0.05 %, 1 times / day Sources: |
healthy, 38 years n = 1 Health Status: healthy Age Group: 38 years Sex: F Population Size: 1 Sources: |
Other AEs: Contact dermatitis... |
0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: |
healthy, 61 years n = 1 Health Status: healthy Age Group: 61 years Sex: M Population Size: 1 Sources: |
Other AEs: Contact dermatitis... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Contact dermatitis | 0.05 % 1 times / day single, topical Studied dose Dose: 0.05 %, 1 times / day Route: topical Route: single Dose: 0.05 %, 1 times / day Sources: |
healthy, 38 years n = 1 Health Status: healthy Age Group: 38 years Sex: F Population Size: 1 Sources: |
|
Contact dermatitis | 0.1 % 1 times / day single, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: single Dose: 0.1 %, 1 times / day Sources: |
healthy, 61 years n = 1 Health Status: healthy Age Group: 61 years Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
Sources: https://cdnsciencepub.com/doi/10.1139/cjpp-2019-0448 Page: 13.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Characterization of antimutagenic mechanism of 3-allyl-5-substituted 2-thiohydantoins against 2-amino-3-methylimidazo[4,5-f]quinoline. | 2005 Apr |
|
Inactivation of Escherichia coli O157:H7 in packaged ground beef by allyl isothiocyanate. | 2005 Apr 1 |
|
Use of mustard flour to inactivate Escherichia coli O157:H7 in ground beef under nitrogen flushed packaging. | 2005 Apr 1 |
|
Nociceptor and hair cell transducer properties of TRPA1, a channel for pain and hearing. | 2005 Apr 20 |
|
How cold is it? TRPM8 and TRPA1 in the molecular logic of cold sensation. | 2005 Apr 22 |
|
Responses of flea beetle Phyllotreta cruciferae to synthetic aggregation pheromone components and host plant volatiles in field trials. | 2005 Aug |
|
Biofumigant compounds released by field pennycress (Thlaspi arvense) seedmeal. | 2005 Jan |
|
Trigeminal sensitization and desensitization in the nasal cavity: a study of cross interactions. | 2005 Jun |
|
Ambient odors influence the amplitude and time course of visual distraction. | 2005 Jun |
|
Differential expression and stability of endogenous nuclear factor E2-related factor 2 (Nrf2) by natural chemopreventive compounds in HepG2 human hepatoma cells. | 2005 Mar 31 |
|
Effects of Brussels sprout juice on the cell cycle and adhesion of human colorectal carcinoma cells (HT29) in vitro. | 2005 May 18 |
|
Pheromonal activity of compounds identified from male Phyllotreta cruciferae: field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate. | 2005 Nov |
|
Biofumigation: environmental impacts on the biological activity of diverse pure and plant-derived isothiocyanates. | 2005 Nov |
|
The role of c-Jun in the AP-1 activation induced by naturally occurring isothiocyanates. | 2005 Sep |
|
Management of root knot nematodes in turfgrass using mustard formulations and biostimulants. | 2006 |
|
Induction of quinone reductase by allylisothiocyanate (AITC) and the N-acetylcysteine conjugate of AITC in Hepa1c1c7 mouse hepatoma cells. | 2006 |
|
Allyl isothiocyanate and its N-acetylcysteine conjugate suppress metastasis via inhibition of invasion, migration, and matrix metalloproteinase-2/-9 activities in SK-Hep 1 human hepatoma cells. | 2006 Apr |
|
Inhibitory effects of microencapsulated allyl isothiocyanate (AIT) against Escherichia coli O157:H7 in refrigerated, nitrogen packed, finely chopped beef. | 2006 Apr 1 |
|
Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils against Lycoriella ingenua (Diptera: Sciaridae). | 2006 Aug |
|
Molecular identification and functional characterization of a temperature-sensitive transient receptor potential channel (TRPM8) from canine. | 2006 Jan 13 |
|
[Studies on chemical components of essential oil of crude semen sinapis and roasted semen sinapis]. | 2006 Jul |
|
Phenethyl isothiocyanate triggers apoptosis in Jurkat cells made resistant by the overexpression of Bcl-2. | 2006 Jul 1 |
|
Impaired nociception and inflammatory pain sensation in mice lacking the prokineticin receptor PKR1: focus on interaction between PKR1 and the capsaicin receptor TRPV1 in pain behavior. | 2006 Jun 21 |
|
Contractile mechanisms coupled to TRPA1 receptor activation in rat urinary bladder. | 2006 Jun 28 |
|
ERK and JNK signaling pathways are involved in the regulation of activator protein 1 and cell death elicited by three isothiocyanates in human prostate cancer PC-3 cells. | 2006 Mar |
|
Modest induction of phase 2 enzyme activity in the F-344 rat prostate. | 2006 Mar 15 |
|
Radioprotective activity of naturally occurring organosulfur compounds. | 2006 Mar-Apr |
|
Invasive plant suppresses the growth of native tree seedlings by disrupting belowground mutualisms. | 2006 May |
|
Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. | 2006 May |
|
Sensitivity to allyl isothiocyanate, dimethyl trisulfide, sinigrin, and cooked cauliflower consumption. | 2006 May |
|
Protective effects of isothiocyanates towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay. | 2006 Nov-Dec |
|
Active packaging of cheese with allyl isothiocyanate, an alternative to modified atmosphere packaging. | 2006 Oct |
|
Changes in glucosinolate concentrations, myrosinase activity, and production of metabolites of glucosinolates in cabbage (Brassica oleracea Var. capitata) cooked for different durations. | 2006 Oct 4 |
|
Protective effects of isothiocyanates towards N-nitrosamine-induced DNA damage in the single-cell gel electrophoresis (SCGE)/HepG2 assay. | 2006 Sep-Oct |
|
Influence of local treatments with capsaicin or allyl isothiocyanate in the sensitization phase of a fluorescein-isothiocyanate-induced contact sensitivity model. | 2007 |
|
Activation of TRPA1 channel facilitates excitatory synaptic transmission in substantia gelatinosa neurons of the adult rat spinal cord. | 2007 Apr 18 |
|
Effects of allyl isothiocyanate from horseradish on several experimental gastric lesions in rats. | 2007 Apr 30 |
|
Characterization of spinal alpha-adrenergic modulation of nociceptive transmission and hyperalgesia throughout postnatal development in rats. | 2007 Aug |
|
Influence of cabbage processing methods and prebiotic manipulation of colonic microflora on glucosinolate breakdown in man. | 2007 Aug |
|
Noxious compounds activate TRPA1 ion channels through covalent modification of cysteines. | 2007 Feb 1 |
|
Active spice-derived components can inhibit inflammatory responses of adipose tissue in obesity by suppressing inflammatory actions of macrophages and release of monocyte chemoattractant protein-1 from adipocytes. | 2007 Feb 13 |
|
Combined effect of volatile antimicrobial agents on the growth of Penicillium notatum. | 2007 Feb 15 |
|
MAK-4 and -5 supplemented diet inhibits liver carcinogenesis in mice. | 2007 Jun 8 |
|
TRP channels as target sites for insecticides: physiology, pharmacology and toxicology. | 2007 Mar |
|
Allyl isothiocyanate (AITC) and phenyl isothiocyanate (PITC) inhibit tumour-specific angiogenesis by downregulating nitric oxide (NO) and tumour necrosis factor-alpha (TNF-alpha) production. | 2007 Mar |
|
Primary and secondary hyperalgesia can be differentiated by postnatal age and ERK activation in the spinal dorsal horn of the rat pup. | 2007 Mar |
|
TRPA1 is differentially modulated by the amphipathic molecules trinitrophenol and chlorpromazine. | 2007 Mar 9 |
|
Methyl p-hydroxybenzoate causes pain sensation through activation of TRPA1 channels. | 2007 May |
|
Activation of TRPA1 channels by the fatty acid amide hydrolase inhibitor 3'-carbamoylbiphenyl-3-yl cyclohexylcarbamate (URB597). | 2007 May |
|
Novel agonistic action of mustard oil on recombinant and endogenous porcine transient receptor potential V1 (pTRPV1) channels. | 2007 May 15 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:00:50 GMT 2023
by
admin
on
Fri Dec 15 15:00:50 GMT 2023
|
Record UNII |
BN34FX42G3
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
JECFA EVALUATION |
ALLYL ISOTHIOCYANATE
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
||
|
CFR |
21 CFR 172.515
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
||
|
IARC | Allyl isothiocyanate | ||
|
EPA PESTICIDE CODE |
4901
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
||
|
NCI_THESAURUS |
C45711
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
ALLYL ISOTHIOCYANATE
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
5572
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
617
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
BN34FX42G3
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
73224
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
C004471
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
CHEMBL233248
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
5971
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
m1556
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | Merck Index | ||
|
300000001589
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
180
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
DTXSID3020047
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
1551
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
200-309-2
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
C68556
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
allyl isothiocyanate
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY | |||
|
57-06-7
Created by
admin on Fri Dec 15 15:00:50 GMT 2023 , Edited by admin on Fri Dec 15 15:00:50 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> AGONIST |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |