General
Preferred name
DIETHYLTOLUAMIDE
Synonyms
DEET ()
Delphene ()
N,N-Diethyl-meta-toluamide ()
N,N-Diethyl-m-toluamide ()
N,N-Diethyl-meta-toluamide, diethyltoluamide ()
Diethyl toluamide ()
Diethyltoluamidum ()
ENT-22542 ()
NSC-33840 ()
ENT-20218 ()
Oristar deet ()
Deet n,n-diethyl-meta-toluamide ()
N,n-diethyl 3-methyl benzamide ()
P&D ID
PD000446
CAS
134-62-3
Tags
natural product
drug
available
Approved by
FDA
Drug Status
approved
Max Phase
Phase 4
Drug indication
Repellant, Arthropod
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION Most diethyltoluamide (DEET) formulations employ the agent as a liquid to be applied onto human skin in an effort to repel mosquitoes from feeding on the skin. Topical application and absorption is consequently the most common route of absorption. When used appropriately, DEET formulations are generally not indicated for too many other routes of absorption or administration, like parenterally or orally.; ; DEET is absorbed quickly through intact skin; 48% of the applied dose is totally absorbed within 6 hours [L2775]. Topical absorption is the usual route of entry as DEET is normally applied to the skin as a mosquito repellent [L2775]. DEET applied to the skin has also been shown to accumulate in the dermis [L2775]. DEET is rapidly absorbed after oral ingestion [L2775]. Additionally, animal experiments demonstrate that DEET can cross the placenta [L2775].; ; DEET is efficiently absorbed across the skin and by the gut [L2779]. Blood concentrations of about 3 mg/L have been reported several hours after dermal application in the prescribed fashion [L2779].; ; Between 9% and 56% of dermally applied DEET is absorbed through the skin with peak blood levels being attained within 1 hour [L2775]. Absorption through the skin varies according to the site exposed to the DEET [L2775]. In animal model surfaces corresponding to the human palmar surface (an area that is typically heavily exposed during the application of liquid DEET), 68% of administered topical DEET was absorbed [L2775]. As a consequence, small children are at increased risk of excessive absorption of DEET applied to the skin because of their relatively higher surface to volume ratio compared to adults [L2775].
MOA The exact mechanism(s) of action by which both (a) insects are repelled by diethyltoluamide (DEET), and (b) humans can be affected deleteriously by exposure to toxic amounts of DEET have not yet been formally elucidated [L2774, L2775, L2777].; ; Research is ongoing regarding the exact mechanism of action by which DEET is capable of repelling insects. However, the most longstanding mechanism proposes that the DEET chemical blocks the olfactory receptors of insects for the volatile 1-octen-3-ol compound that is an element in human sweat and breath [A33052]. As a consequence, this proposed mechanism suggests that the blockade of insects' senses for this 1-octen-3-ol blinds and prevents the triggering of their biting and/or feeding instinct on humans and other animals that produce that compound [A33052]. Nevertheless, this theory has not yet been fully elucidated.; ; Furthermore, recent studies have demonstrated that DEET binds to certain molecular targets like the Anopheles gambiae odorant binding protein 1 (AgamOBP1) with high shape complementarity [A33053] and the antennae-specific odorant receptor CquiOR136 of the southern house mosquito, Culex quinquefasciatus [L2778]. In southern house mosquitos with reduced CquiOR136 transcript levels, behavioral tests demonstrated that this phenotype showed demonstrably lower responses/repulsion to DEET [L2778]. Again, however, such findings require continued research and do not formally elucidate the mechanism of action by which DEET can repel insects.; ; And finally, the mechanism of toxicity in which DEET is capable of eliciting effects of neurotoxicity in humans who have been exposed to toxic levels of the agent is also poorly understood [L2775, A33054]. A recent study proposes that DEET is capable of blocking Na+ and K+ channels in the rat animal model [A33054]. This ion channel blocking activity of DEET in neurons may subsequently contribute to the kind of neuro-sensory adverse effects like numbness experienced after inadvertent application to the lips or mouth of humans [A33054].
Compound Sets
14
ChEMBL Approved Drugs
CHEMBL1453317
ChEMBL Drugs
CHEMBL1453317
Drug Repurposing Hub
DrugBank
DB11282
DrugBank Approved Drugs
DB11282
DrugCentral
4418
DrugCentral Approved Drugs
4418
Enamine BioReference Compounds
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1453317
MedChem Express Bioactive Compound Library
HY-B0978
NPC Screening Collection
Selleckchem Bioactive Compound Library
deet
TargetMol Bioactive Compound Library
T0731
The Spectrum Collection
External IDs
31
Properties
(calculated by RDKit )
Molecular Weight
191.13
Hydrogen Bond Acceptors
1
Hydrogen Bond Donors
0
Rotatable Bonds
3
Ring Count
1
Aromatic Ring Count
1
cLogP
2.48
TPSA
20.31
Fraction CSP3
0.42
Chiral centers
0.0
Largest ring
6.0
QED
0.72
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Neuroscience
Anti-infection
Target
AChE
Parasite
Indication
sunscreen lotion
MOA
ionotropic receptor IR40a activator
Source data