Compounds > ethyl-3-(n-n-butyl-n-acetyl)aminopropionate
Page last updated: 2024-11-07

ethyl-3-(n-n-butyl-n-acetyl)aminopropionate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

ethyl-3-(N-n-butyl-N-acetyl)aminopropionate: an insect repellent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID104150
CHEMBL ID2230259
CHEBI ID81991
SCHEMBL ID16475
MeSH IDM0435030

Synonyms (64)

Synonym
n-acetyl-n-butyl-.beta.-alanine ethyl ester
insect repellent m 3535
repellent 3535
ethyl butylacetylaminopropionate
52304-36-6
ethyl n-acetyl-n-butyl-|a-alaninate
ethyl 3-[acetyl(butyl)amino]propanoate
ethyl 3-(n-butylacetamido)propionate
C18830
NCGC00255638-01
dtxsid9035753 ,
cas-52304-36-6
tox21_301772
dtxcid7015753
ethyl n-acetyl-n-butyl-beta-alaninate
n-acetyl-n-butyl-beta-alanine ethyl ester
ethyl-3-(n-n-butyl-n-acetyl)aminopropionate
3-(n-n-butyl-n-acetyl)aminopropionic acid ethyl ester
einecs 257-835-0
ir 3535
ebaap
ai 3-70763
baape
eus 26-15
merck 3535
unii-65gqa237eh
hsdb 8318
ir3535
quwenzhi
65gqa237eh ,
n-acetyl-n-butyl-beta-alanine, ethyl ester
beta-alanine, n-acetyl-n-butyl-, ethyl ester
FT-0630653
AKOS015914988
insect repellent 3535
ethyl butylacetylaminopropionate [jan]
ethyl-3-(n-butylacetamido)propionate
ethyl butylacetylaminopropionate [inci]
ethyl butylacetylaminopropionate [mi]
ir-3535
3-(n-butyl-n-acetyl)-aminopropionic acid ethyl ester
SCHEMBL16475
CHEMBL2230259
chebi:81991 ,
3-(n,n-butyl-n-acetyl)aminopropionic acid ethyl ester
Q-201664
3-[n-n-butyl-n-acetyl]aminopropionic acid ethyl ester, aldrichcpr
DTXSID00241810 ,
ethyl 3-(n-butylacetamido)propanoate
ethyl butylacetylaminopropionate, pestanal(r), analytical standard
3-[n-n-butyl-n-acetyl]aminopropionic acid-ethyl ester
ethyl butylacetylaminopropanoate
DS-3340
Q5973365
mfcd00214076
ethyl butylacetylaminopropionate (jan)
D11818
D97457
CS-0152121
ir3535 (ethyl 3-(n-utylacetamido)propanoate)
ethyl 3-
dtxcid30164301
ethyl 3-(n-acetyl-n-butylamino)propionate
aquax repellent

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" EBAAP was toxic to zebrafish, with a lethal concentration 50 (LC50) of 140 mg/L at 72 hours post fertilization (hpf)."( Developmental and cardiac toxicity assessment of Ethyl 3-(N-butylacetamido) propanoate (EBAAP) in zebrafish embryos.
Ai, L; Chen, X; Cheng, B; Lu, H; Luo, Q; Ma, J; Tang, S; Tian, G; Xiao, X; Xiong, C; Zhang, H; Zhong, K, 2023)		0.91

Dosage Studied

ExcerptRelevanceReference
" I began with pretrial studies of dosing behavior to compute formula-specific mean dosing rates for the subsequent efficacy trials."( Prolonged efficacy of IR3535 repellents against mosquitoes and blacklegged ticks in North America.
Carroll, SP, 2008)		0.35
" All EOs were repellent, followed a dose-response relationship, and had bioactivity similar to or better than that of commercial compound IR3535."( Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
Caballero-Gallardo, K; Olivero-Verbel, J; Stashenko, EE, 2011)		0.37
"Here, we performed IR3535 dose-response analyses on Drosophila melanogaster, a well-known insect model organism, using electrophysiology and binary food choice assays."( Cellular and molecular basis of IR3535 perception in Drosophila.
Lee, Y; Nath, DK; Nhuchhen Pradhan, R; Shrestha, B, 2022)		0.72
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
tertiary carboxamideA carboxamide resulting from the formal condensation of a carboxylic acid with a secondary amine; formula RC(=O)NHR(1)R(2).
acetamidesCompounds with the general formula RNHC(=O)CH3.
ethyl esterAny carboxylic ester resulting from the formal condensation of the carboxy group of a carboxylic acid with ethanol.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency0.34380.003041.611522,387.1992AID1159552
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency61.64480.001024.504861.6448AID743215
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency54.94100.023723.228263.5986AID743223
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1081894Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 2 hr post compound exposure at 0.0002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081886Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 4 hr post compound exposure at 0.2 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081893Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 2 hr post compound exposure at 0.002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081889Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 4 hr post compound exposure at 0.0002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081887Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 4 hr post compound exposure at 0.02 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081892Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 2 hr post compound exposure at 0.02 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081891Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 2 hr post compound exposure at 0.2 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081895Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 2 hr post compound exposure at 0.00002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081890Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 4 hr post compound exposure at 0.00002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
AID1081888Repellent activity against Tribolium castaneum (red flour beetle) assessed as induction of repellency measured 4 hr post compound exposure at 0.002 uL/cm2 using 15% compound formulation2011Journal of agricultural and food chemistry, Mar-09, Volume: 59, Issue:5
Repellent activity of essential oils and some of their individual constituents against Tribolium castaneum herbst.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (53)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (1.89)18.7374
1990's0 (0.00)18.2507
2000's20 (37.74)29.6817
2010's25 (47.17)24.3611
2020's7 (13.21)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.37

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.37 (24.57)
Research Supply Index4.08 (2.92)
Research Growth Index4.44 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.37)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (7.41%)5.53%
Reviews3 (5.56%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other47 (87.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
beta-alanine
[no description available]		6.46131amino acid zwitterion;
beta-amino acid		agonist;
fundamental metabolite;
human metabolite;
inhibitor;
neurotransmitter
menthol
Menthol: A monoterpene cyclohexanol produced from mint oils.		2.9940p-menthane monoterpenoid;
secondary alcohol		volatile oil component
benzyl benzoate
benzyl benzoate: structure; acarosan, a moist powder composed of wetted cellulose and benzyl benzoate, is used on carpets as an acaricide. benzyl benzoate : A benzoate ester obtained by the formal condensation of benzoic acid with benzyl alcohol. It has been isolated from the plant species of the genus Polyalthia.		2.0610benzoate ester;
benzyl ester		acaricide;
plant metabolite;
scabicide
lauric acid
dodecanoic acid : A straight-chain, twelve-carbon medium-chain saturated fatty acid with strong bactericidal properties; the main fatty acid in coconut oil and palm kernel oil.		2.0310medium-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
antibacterial agent;
plant metabolite
deet
N,N-diethyl-m-toluamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of m-toluic acid with the nitrogen of diethylamine. First developed by the U.S. Army in 1946 for use by military personnel in insect-infested areas, it is the most widely used insect repellent worldwide.		8.84343benzamides;
monocarboxylic acid amide		environmental contaminant;
insect repellent;
xenobiotic
niclosamide
Niclosamide: An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48). niclosamide : A secondary carboxamide resulting from the formal condensation of the carboxy group of 5-chlorosalicylic acid with the amino group of 2-chloro-4-nitroaniline. It is an oral anthelmintic drug approved for use against tapeworm infections.		2.0310benzamides;
C-nitro compound;
monochlorobenzenes;
salicylanilides;
secondary carboxamide		anthelminthic drug;
anticoronaviral agent;
antiparasitic agent;
apoptosis inducer;
molluscicide;
piscicide;
STAT3 inhibitor
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		1.9710alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
terpin
terpene : A hydrocarbon of biological origin having carbon skeleton formally derived from isoprene [CH2=C(CH3)CH=CH2].		2.9940p-menthane monoterpenoid
4-cymene
4-cymene: structure. p-cymene : A monoterpene that is toluene substituted by an isopropyl group at position 4.		2.0610monoterpene;
toluenes		human urinary metabolite;
plant metabolite;
volatile oil component
benzyl salicylate
benzyl salicylate: structure given in Merck		2.0610benzoate ester;
phenols
citronellol
citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.		2.0610monoterpenoidplant metabolite
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.110cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
carvacrol
carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).		2.0610botanical anti-fungal agent;
p-menthane monoterpenoid;
phenols		agrochemical;
antimicrobial agent;
flavouring agent;
TRPA1 channel agonist;
volatile oil component
carvone, (s)-isomer
(+)-carvone : A carvone having (S) configuration.		2.0610carvone
hexamethyldisiloxane
dimethicone: a linear silicone; an ingredient of SIMETHICONE; lotion of dimeticone in a volatile silicone base has been used to treat LICE		2.0310organosiloxane
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.110benzenes;
phenyl acetates
myrcene
myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.		2.0610monoterpeneanabolic agent;
anti-inflammatory agent;
flavouring agent;
fragrance;
plant metabolite;
volatile oil component
nonanal
nonanal : A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism.		2.110medium-chain fatty aldehyde;
n-alkanal;
saturated fatty aldehyde		human metabolite;
plant metabolite
permethrin
hemoglobin Atlanta-Coventry: Leu replaced by Pro at beta75 and Leu deleted at beta141		3.8530cyclopropanecarboxylate ester;
cyclopropanes		agrochemical;
ectoparasiticide;
pyrethroid ester acaricide;
pyrethroid ester insecticide;
scabicide
decamethrin
decamethrin: pyrethroid insecticide; RN given refers to cpd without isomeric designation; structure		2.5420aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organobromine compound		agrochemical;
antifeedant;
calcium channel agonist;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
pyrethroid ester insecticide
picaridin
picaridin: picaridin is the (R,S)-isomer; an insect repellent		7.81211carboxylic acid;
piperidines
geraniol
[no description available]		2.06103,7-dimethylocta-2,6-dien-1-ol;
monoterpenoid;
primary alcohol		allergen;
fragrance;
plant metabolite;
volatile oil component
citral
citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.		2.0610enal;
monoterpenoid;
polyprenal		plant metabolite;
volatile oil component
nerol
nerol : The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass.		2.06103,7-dimethylocta-2,6-dien-1-olfragrance;
plant metabolite;
volatile oil component
geranyl acetate
geranyl acetate: constituted about 90% of the palmarosa oil. geranyl acetate : A monoterpenoid that is the acetate ester derivative of geraniol.		2.0610acetate ester;
monoterpenoid		plant metabolite
cyhalothrin
cyhalothrin: acaricidal & insecticidal synthetic pyrethroid; structure given in first source. cyhalothrin : A carboxylic ester obtained by formal condensation between 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol.		2.1110aromatic ether;
cyclopropanecarboxylate ester;
nitrile;
organochlorine compound;
organofluorine compound		agrochemical;
pyrethroid ester acaricide;
pyrethroid ester insecticide
methyl jasmonate
[no description available]		2.110
piperidines
Piperidines: A family of hexahydropyridines.		7.81211
pyrethrins
[no description available]		3.8630
ConditionIndicatedRelationship StrengthStudiesTrials
Cardiac Toxicity
[description not available]		02.610
Cardiotoxicity
Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.		02.610
Tick Bites
The effects, both local and systemic, caused by the bites of TICKS.		03.4220
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.4320
Insect Bites
[description not available]		06.5101
Insect Bites and Stings
Bites and stings inflicted by insects.		06.5101
Infections, Tick-Borne
[description not available]		04.7521
Congenital Zika Syndrome
[description not available]		02.4110
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.4110
Mosquito Borne Diseases
[description not available]		02.4110
Bites
[description not available]		02.1110
Encephalitis, West Nile Fever
[description not available]		02.0410
West Nile Fever
A mosquito-borne viral illness caused by the WEST NILE VIRUS, a FLAVIVIRUS and endemic to regions of Africa, Asia, and Europe. Common clinical features include HEADACHE; FEVER; maculopapular rash; gastrointestinal symptoms; and lymphadenopathy. MENINGITIS; ENCEPHALITIS; and MYELITIS may also occur. The disease may occasionally be fatal or leave survivors with residual neurologic deficits. (From Joynt, Clinical Neurology, 1996, Ch26, p13; Lancet 1998 Sep 5;352(9130):767-71)		02.0410
Infections, Plasmodium
[description not available]		02.4420
Malaria
A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia.		02.4420
Bilharziasis
[description not available]		02.0110
Parasitic Skin Diseases
[description not available]		02.0110
Dermatitis
Any inflammation of the skin.		02.4320
Schistosomiasis
Infection with flukes (trematodes) of the genus SCHISTOSOMA. Three species produce the most frequent clinical diseases: SCHISTOSOMA HAEMATOBIUM (endemic in Africa and the Middle East), SCHISTOSOMA MANSONI (in Egypt, northern and southern Africa, some West Indies islands, northern 2/3 of South America), and SCHISTOSOMA JAPONICUM (in Japan, China, the Philippines, Celebes, Thailand, Laos). S. mansoni is often seen in Puerto Ricans living in the United States.		02.0110
Fasciolopsiasis
[description not available]		02.0310