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Piperazine
Last updated: 04/03/2020
(Also known as: hexahydropyrazine; piperazidine; diethylenediamine; dispermine; 1,4-piperazine)

GENERAL INFORMATION
Description
Medicinal drug used in the treatment of intestinal roundworm infections
Availability status
-
Introduction & key dates
1953, first use as an anthelmintic
Examples of species treated
Cats, Dogs, Poultry, Horses, Pigs
Chemical structure
Isomerism
-
Chemical formula
C₄H₁₀N₂
Canonical SMILES
C1CNCCN1
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
GLUUGHFHXGJENI-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
piperazine -
General status
Veterinary substance type
Anthelmintic, Medicinal drug, Antiparastic
Substance group
Hetrocyclic
Minimum active substance purity
99.9
Known relevant impurities
None declared
Substance origin
Synthetic
Mode of action
Acts by paralysing the parasite. Acts as a weak GABA-mimetic and causes a flaccid, reversible paralysis of body wall muscle
Molecular targets
[Gamma-aminobutyric-acid (GABA) receptor subunit beta-3, agonist]
CAS RN
110-85-0
EC number
203-808-3
CIPAC number
-
US EPA chemical code
-
PubChem CID
-
ATCvet Code
QP52AH01
Therapeutic Class
Antiparasitic products, insecticides & repellents: Anthelmintics
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: Porcine, Chicken)
Molecular mass
86.14
PIN (Preferred Identification Name)
-
IUPAC name
1,4-diethylenediamine
CAS name
hexahydro-1,4-diazine
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Off-white or colourless deliquescent crystals
Formulations
Property
Product
Manufacturer
Authorisation Route
UK Legal Class
Example products using this active
Beaphar Worming Syrup Beaphar UK Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Dual Action Worming Tablets for Cats Battle, Hayward & Bower Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Johnson's Twin-Wormer for Cats Johnsons Veterinary Products Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Piperazine Citrate Worm Tablets Ayrton Saunders Ltd UK National authorisation Authorised veterinary medicine for general sale (AVM - GSL)
Formulation and application details
Usually supplied in tablet form for oral administration
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
150000
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
at pH 12
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
107
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Boiling point (°C)
148
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Degradation point (°C)
- - -
Flashpoint (°C)
65
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Octanol-water partition coefficient at pH 7, 20 °C
P
7.59 X 10-02 Calculated -
Log P
-1.12
R4 R = Peer reviewed scientific publications
4 = Verified data
Low
Bulk density (g ml⁻¹)
1.1
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Dissociation constant pKa) at 25 °C
4.19
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Strong base
Vapour pressure at 20 °C (mPa)
21280
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
Does not absorb at wavelengths >290 nm
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
-
Surface tension (mN m⁻¹)
- - -
Refractive Index
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
Note
-
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
CA2 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
2 = Unverified data of unknown source
Very mobile
Koc
3.1
Notes and range
Estimated
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
- - -
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
N -mononitrosopiperazine MNPz Human (Liver) - -
N-nitroso-3-hydroxypyrrolidine
Note: Secondary metabolite
NHPYR Human (Liver) - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
3.9
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Cyprinus carpio
Low potential
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 5000
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
Low
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)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 100
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
Unknown species
Low
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
> 21.0
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
> 12.5
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Low
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 - Acute 7 day EC₅₀, biomass (mg l⁻¹)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻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)
- - -
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 pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
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)
> 5000
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
4000
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 5.4
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat 2 hr
-
Other Mammal toxicity endpoints
Subcutaneous LD₅₀ = 3700 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
Intravenous LD₅₀ = 1340 mg kg⁻¹
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
Rat
-
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
-
Elimination route and rate
Urinary excretion is the primary route of elimination in humans
CA3 CA = Medical and toxicological databases and information systems e.g. TOXNET (click here )
3 = Unverified data of known source
-
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
No data found No data found
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
?Possibly, status not identified
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
May induce chronic bronchitis and cause breathing difficulties
Handling issues
Property
Value and interpretation
General
Corrosive
Hygroscopic
Flammable
IMDG Transport Code is 8
Explosion limits in air: 4-14 % vol
CLP classification 2013
-
EC Risk Classification
Xn - Harmful: R52, R42, R43
Xi - Irritant: R36, R37, R38
H - Handling risks: R10, R34
Harmful for the environment: R53
EC Safety Classification
S22, S26, S36, S37, S39, S45, S61
WHO Classification
None - not a ppp
UN Number
2579
Waste disposal & packaging
Packaging Group III (minor danger)
TRANSLATIONS
Language
Name
English
piperazine
French
-
German
Piperazin
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-

Record last updated: 04/03/2020
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