Nitenpyram (Ref: CGA 246916)

Nitenpyram (Ref: CGA 246916)	Last updated: 15/09/2025
(Also known as: (E)-nitenpyram ; TI 204; niterndipoine)

GENERAL INFORMATION

Description

A systemic insecticide used mainly to kill external parasites in livestock and domestic pets

Examples of veterinary uses

Mainly used to treat adult flea infestations in mammals and maggot infestations on reptiles as off-label

Examples of species treated

Cats; Dogs; Reptiles

Approval status

VMR 2013/2033 approval status (GB/UK)

Approved - usually available as an authorised veterinary medicine for general sale (AVM-GSL)

EU Regulatory approval status

Approved

Chemical structure

Isomerism

Nitenpyram exhibits geometrical (E/Z) isomerism, which arises from the presence of a C=C double bond in its nitroethene moiety. Specifically, the molecule contains a 2-nitroethene-1,1-diamine structure where the substituents around the double bond can adopt different spatial arrangements. The commercially active form is the (E)-isomer, meaning the bulky groups on either side of the double bond are positioned opposite each other, which contributes to its biological activity and stability.

Chemical formula

C₁₁H₁₅ClN₄O₂

Canonical SMILES

CCN(CC1=CN=C(C=C1)Cl)C(=C[N+](=O)[O-])NC

Isomeric SMILES

CCN(CC1=CN=C(C=C1)Cl)/C(=C/[N+](=O)[O-])/NC

International Chemical Identifier key (InChIKey)

CFRPSFYHXJZSBI-DHZHZOJOSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H15ClN4O2/c1-3-15(11(13-2)8-16(17)18)7-9-4-5-10(12)14-6-9/h4-6,8,13H,3,7H2,1-2H3/b11-8+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
nitenpyram	-

General status

Veterinary substance type

Insecticide, Antiparasitic

Substance groups

Neonicotinoid insecticide

Minimum active substance purity

>98%

Known relevant impurities

Substance origin

Semi-synthetic

Mode of action

Systemic with translaminar activity, stomach and contact action affecting insects nervous system. No long term activity. Nicotinic acetylcholine receptor (nAChR) channel blocker.

Molecular targets

[Nicotinic acetylcholine receptors, Binder]

CAS RN

150824-47-8

EC number

634-900-5

CIPAC number

None allocated

US EPA chemical code

PubChem CID

3034287

CLP index number

No data found

Therapeutic Class

Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents

ATCvet Code

QP53BX02

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

270.72

PIN (Preferred Identification Name)

(1E)-N-[(6-chloropyridin-3-yl)methyl]-N-ethyl-N'-methyl-2-nitroethene-1,1-diamine

IUPAC name

(E)-N-(6-chloro-3-pyridylmethyl)-N-ethyl-N'-methyl-2-nitrovinylidenediamine

CAS name

(1E)-N-[(6-chloro-3-pyridinyl)methyl]-N-ethyl-N'-methyl-2-nitro-1,1-ethenediamine

Forever chemical

Other status information

PAN listed Highly Hazardous Chemical

Relevant Environmental Water Quality Standards

Physical state

Pale yellow to orange crystalline solid

Commercial

Property

Value

Availability status

Current

Introduction & key dates

1989, discovered, 1995, launched

Example manufacturers & suppliers of products using this active now or historically

Sumitomo
Novartis Animal Health
BOC Sciences
Elanco Europe Ltd

Example products using this active

BestGuard
Capstar
Bob Martin Flea Tablets
Capstar Tablets
Johnsons 4Fleas Tablets

Formulation and application details

Usually supplied as a dusting powder, granules, drops and impregnated collars for topical use and as tablets for oral treatments.

Commercial production

The commercial synthesis of nitenpyram involves a streamlined multi-step process that begins with the preparation of two key intermediates: 1,1,1-trichloro-2-nitroethane, synthesised via elimination and catalytic nitration of 1,1,1,2-trichloroethane, and N-ethyl-2-chloro-5-pyridylmethylamine, obtained through N-alkylation of 2-chloro-5-nitropyridine using phase-transfer catalysis in aqueous media. These intermediates are then combined in a single reaction vessel using dichloromethane as a solvent, where condensation and methylamination reactions occur to form the final nitenpyram molecule. The product is subsequently extracted, desolventised, and crystallised.

Impact on climate of production and use

Data for the amount of life cycle GHGs produced by nitenpyram are not available in the public domain. However, whilst estimates vary, more general data suggests that between 14 and 19 kilograms of CO₂e is emitted per kilogram of insecticide produced.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

570000

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

1000000

Methanol

700000

Chloroform

290000

Acetone

4500

Xylene

Melting point (°C)

Boiling point (°C)

417.2

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

2.19 X 10^-01

Calculated

Log P

-0.66

at 25 °C

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.254

Dissociation constant pKa) at 25 °C

3.1

Vapour pressure at 20 °C (mPa)

0.0011

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.54 X 10^-13

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

General literature states DT₅₀ 1-15 days

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Stable

Note

Stable pH 3-7 at 25 °C; pH9 DT₅₀ = 2.9 days

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Mobile

K_oc (mL g⁻¹)

Notes and range

Estimated

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.01

Calculated

Transition state

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl-N-methylformamidine

3-CPMF

Plant

2-(N-(6-chloro-3-pyridylmethyl)-N-ethyl)amino-2-methyliminoacetic acid

2-CPMA

Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1575

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

1124

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹ dw soil)

32.2

Moderate

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹ dw soil)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Vegetative vigour ER₅₀ (g ha⁻¹)

Seedling emergence ER₅₀ (g ha⁻¹)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

0.138

High

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings) as Mortality, Contact LC₅₀ ppm

> 0.33

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

10000

Daphnia magna

Low

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic Plants (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)

Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)

Algae - Acute (growth rate, fresh; mg l⁻¹) (EC₅₀)

26.0

Raphidocelis subcapitata

Low

Algae - Chronic (growth rate, fresh; mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1575

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

5.8

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

In mammals it is excreted mostly unchanged in the urine

Health issues

Specific human health issues (hazard-based)

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Corrosive

CLP classification 2013

Health: H302, H315, H319, H335
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Limited shelf-life. Store at -20 DegC

TRANSLATIONS

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English

nitenpyram

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Record last updated:	15/09/2025
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242