Basic information
- Standard SMILES
C1CNCCN1.Cl.Cl- InChIKey
CVVIJWRCGSYCMB-UHFFFAOYSA-N- Molecular formula
- C4H12Cl2N2
- Average molar mass
- 159.05 g/mol
- Monoisotopic mass
- 158.0377538
Names & identifiers
- Preferred name
- Piperazine Dihydrochloride
- IUPAC
- piperazine;dihydrochloride
- English name
- PIPERAZINE DIHYDROCHLORIDE
- Molecular formula
- C4H12Cl2N2
- Molecular weight
- 159.06
Names & synonyms
Show more names
Database identifiers
- CAS
142-64-3、7542-23-6- PubChem CID
- 8893
- DTXSID
DTXSID4047096- ChEMBL
CHEMBL3188015- UNII
- 17VU4Z4W88
- EC Number
- 205-551-2、231-422-5
Properties
Computed structural properties
- Topological polar surface area
- 24.1 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 26
Experimental & physicochemical properties
Color/Form
CREAM COLORED CRYSTALLINE POWDER
WHITE NEEDLES
White to creamy colored needles or powder.
Solubility
41 % (NIOSH, 2024)
SOLUBILITY IN WATER: 35% @ 0 °C, 41% @ 20 °C, 48% @ 50 °C; INSOL IN ORGANIC SOLVENTS
41%
Melting Point
635 °F (NIOSH, 2024)
635 °F
635 °F
Physical Description
Piperazine dihydrochloride appears as white to cream-colored needles or powder. Mp: 318-20 °C (with decomposition).
White to cream-colored needles or powder; [NIOSH]
White to cream-colored needles or powder.
White to cream-colored needles or powder.
Stability/Shelf Life
STABLE @ TEMP TO 270 °C & IN NEUTRAL OR ACID MEDIA
Stability of piperazine can be accomplished by use of its simple salts, /including hydrochloride/, which are more stable than the piperazine base.
Other Experimental Properties
SLIGHTLY HYGROSCOPIC
82-83 °C /Monohydrate/
Physicochemical properties
- Melting point
- 320 °C · 320°C(dec.)(lit.)
- Boiling point
- 262.01 °C · 262.01°C (rough estimate)
- Density
- 1.3011 · 1.3011 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Water
- form
- White crystalline solid
- color
- White to Off-White
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1S/C4H10N2.2ClH/c1-2-6-4-3-5-1;;/h5-6H,1-4H2;2*1H
- InChIKey
- CVVIJWRCGSYCMB-UHFFFAOYSA-N
- SMILES
- C1NCCNC1.Cl.Cl
- LogP
- -1.171 · -1.171 (est)
- CAS DataBase Reference
- 142 · 142-64-3(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- PIPERAZINE DIHYDROCHLORIDE
- FDA UNII
- 17 VU4Z4W88 · 17VU4Z4W88
- EPA Substance Registry System
- Piperazine dihydrochloride (142-64-3)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Danger
- Hazard statements
- 315 · H315-H319-H334-H361fd-H412
- Precautionary statements
- 202 · P202-P261-P273-P302+P352-P305+P351+P338-P308+P313
- Hazard Codes
- Xn
- Risk Statements
- 36 · 36/37/38-42/43
- Safety Statements
- 22 · 22-26-36/37
- OEB
- B
- OEL
- 5 mg/m3 · TWA: 5 mg/m3
- WGK Germany
- 2 · WGK 2
- RTECS
- 4025000 · TL4025000
- F
- 3 · 3-10
- TSCA
- TSCA listed
- HS Code
- 2933599550 · 2933599550
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Irrit. 2Repr. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1
- Hazardous Substances Data
- 142 · 142-64-3(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,intraperitoneal,1970mg/kg (1970mg/kg),LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION,Japanese Journal of Pharmacology. Vol. 17, Pg. 475, 1967.
Safety & regulation
GHS classification
GHS Classification
Danger
H315: Causes skin irritation [Warning Skin corrosion/irritation];H317: May cause an allergic skin reaction [Warning Sensitization, Skin];H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation];H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H361fd: Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity];H412: Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P203, P233, P260, P261, P264, P264+P265, P271, P272, P273, P280, P284, P302+P352, P304+P340, P305+P351+P338, P318, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P405, and P501 (click each P-code to see the statement)
Danger
Hazard information
Regulatory Information
Chemical: Piperazine, dihydrochloride
Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient
Piperazine dihydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Health Hazards
Excerpt from NIOSH Pocket Guide for Piperazine dihydrochloride:;Exposure Routes: Inhalation, skin absorption, ingestion, skin and/or eye contact;Symptoms: Irritation eyes, skin, respiratory system; skin burns, sensitization; asthma; gastrointestinal upset, headache, nausea, vomiting, incoordination, muscle weak;Target Organs: Eyes, skin, respiratory system, central nervous system (NIOSH, 2024)
Hazards Summary
Piperazine dihydrochloride is well tolerated as an oral medication at a dose of 150 mg/kg for several days. Skin burns, allergic contact dermatitis, and asthma have been reported after occupational exposures to piperazine dust. [ACGIH] Piperazine, CAS # 110-85-0, is corrosive to skin. [Quick CPC] Asthma reported in pharmaceutical and chemical production workers; [Malo] Allergic contact dermatitis reported in pharmaceutical, laboratory, healthcare, and veterinary workers; [Kanerva, p. 1827] See Piperazine and salts.
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Hazard Classes and Categories
Skin Irrit. 2 (100%);Skin Sens. 1 (97.6%);Eye Irrit. 2 (100%);Resp. Sens. 1 (97.6%);Repr. 2 (92.9%);Aquatic Chronic 3 (95.2%)
Eye irritation - category 2A;Skin irritation - category 2;Specific target organ toxicity (single exposure) - category 1;Specific target organ toxicity (repeated exposure) - category 2;Respiratory sensitisation - category 1;Skin sensitisation - category 1;Hazardous to the aquatic environment (chronic) - category 3;Reproductive toxicity - category 2
Acute toxicity (Oral) - Category 5;Skin corrosion/irritation - Category 2;Serious eye damage/eye irritation - Category 2A-2B
Repr. 2;Skin Irrit. 2;Eye Irrit. 2;Resp. Sens. 1;Skin Sens. 1;Aquatic Chronic 3
Hazardous Reactivities and Incompatibilities
Water [Note: Slightly hygroscopic (i.e., absorbs moisture from the air)].
Water [Note: Slightly hygroscopic (i.e., absorbs moisture from the air).]
Safety & protection
First Aid
Excerpt from NIOSH Pocket Guide for Piperazine dihydrochloride:;Eye: IRRIGATE IMMEDIATELY - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: WATER FLUSH IMMEDIATELY - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.;Breathing: RESPIRATORY SUPPORT - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.;Swallow: MEDICAL ATTENTION IMMEDIATELY - If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2024)
(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Water flush immediately - If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
If material not on fire and not involved in fire: Keep sparks, flames, and othersources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. /Piperazine/
Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. If contact with the material anticipated, wear appropriate chemical protective clothing. /Piperazine/
The worker should immediately wash the skin when it becomes contaminated.
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
Threshold Limit Values (TLV)
8 hr Time Weighted Avg (TWA): 5 mg/cu m.
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.
0.03 ppm (inhalable fraction and vapor) [2011]
Recommended Exposure Limit (REL)
5 mg/m³
TWA 5 mg/m3
Personal Protective Equipment (PPE)
Excerpt from NIOSH Pocket Guide for Piperazine dihydrochloride:;Skin: PREVENT SKIN CONTACT - Wear appropriate personal protective clothing to prevent skin contact.;Eyes: PREVENT EYE CONTACT - Wear appropriate eye protection to prevent eye contact.;Wash skin: WHEN CONTAMINATED - The worker should immediately wash the skin when it becomes contaminated.;Remove: WHEN WET OR CONTAMINATED - Work clothing that becomes wet or significantly contaminated should be removed and replaced.;Change: DAILY - Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.;Provide:;⢠EYEWASH - Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substances; this is irrespective of the recommendation involving the wearing of eye protection.;⢠QUICK DRENCH - Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2024)
Wear appropriate personal protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.
Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.]
Toxicology
Interactions
IN ISOLATED FROG & RABBIT HEARTS PIPERAZINE PRODUCED BIPHASIC EFFECT WITH INITIAL NEG INOTROPIC ACTION FOLLOWED BY POS INOTROPIC ACTION. FORMER PHASE WAS ANTAGONIZED BY ATROPINE, HEXAMETHONIUM & DIGOXIN. DIRECT ACTION ON THE HEART IS SUGGESTED. /PIPERAZINE HYDROGEN CHLORIDE/
Human Toxicity Excerpts
... SIDE EFFECTS ... INCL HEADACHES, NAUSEA, VOMITING, DIARRHEA, LETHARGY, TREMOR, INCOORDINATION, MUSCULAR WEAKNESS ... & VAGUE OCULAR DISTURBANCES. /PIPERAZINE SALTS/
LOSS OF CONSCIOUSNESS, DYSARTHRIA, APRAXIA, CLONIC SPASMS, TREMOR, MUSCULAR WEAKNESS, DROPPING OF OBJECTS, INABILITY TO THINK CLEARLY &/OR HALLUCINATIONS SEEN IN 35 YR OLD PT WITH TERMINAL RENAL FAILURE TAKING 30 MG PIPERAZINE HEXAHYDRATE/KG BODY WT/DAY FOR 10 DAYS. /PIPERAZINE HEXAHYDRATE/
SEVERE ILLNESS OCCURRED IN A 25 YR OLD WOMAN AFTER ADMIN OF PIPERAZINE ON 2 SEPARATE OCCASIONS. EVIDENCE FAVORS A HYPERSENSITIVITY MECHANISM RATHER THAN A DIRECT TOXIC EFFECT OF DRUG OR ITS METABOLITES. /PIPERAZINE/
ACUTE HUMAN EXPOSURES HAVE RESULTED IN MILD TO MODERATE SKIN BURNS & SENSITIZATION. MILD TO MODERATE ASTHMA HAS BEEN ASSOCIATED WITH INHALATION OF DUST.
Non-Human Toxicity Excerpts
EYE CONTACT, MARKED PAIN AND MODERATE EYE IRRITATION WHICH HEALS IN 2 DAYS WITH NO CORNEAL INJURY. SKIN CONTACT VERY SLIGHT IRRITATION.
VOMITING & DIARRHEA IS OCCASIONALLY REPORTED IN CATS & DOGS ESPECIALLY IF OVERDOSED. /ORAL ADMIN/
IN ISOLATED FROG & RABBIT HEARTS PIPERAZINE PRODUCED BIPHASIC EFFECT WITH INITIAL NEG INOTROPIC ACTION FOLLOWED BY POS INOTROPIC ACTION. FORMER PHASE WAS ANTAGONIZED BY ATROPINE, HEXAMETHONIUM & DIGOXIN. DIRECT ACTION ON HEART IS SUGGESTED. /PIPERAZINE/
Regulatory information
Regulatory Information
Chemical: Piperazine, dihydrochloride
Hazard Traits - Respiratory Toxicity;Authoritative List - EC Annex VI Resp. Sens. - Cat. 1;Report - if used as a fragrance or flavor ingredient
Piperazine dihydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Safety data
- F
- 3-10
- OEB
- B
- OEL
- TWA: 5 mg/m3
- wgk
- WGK 2
- tsca
- TSCA listed
- rtecs
- TL4025000
- hs_code
- 2933599550
- Toxicity
- mouse,LD50,intraperitoneal,1970mg/kg (1970mg/kg),LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION,Japanese Journal of Pharmacology. Vol. 17, Pg. 475, 1967.
- risk_code
- 36/37/38-42/43
- Signal word
- Danger
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-26-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H334-H361fd-H412
- Hazard Classifications
- Aquatic Chronic 3Eye Irrit. 2Repr. 2Resp. Sens. 1Skin Irrit. 2Skin Sens. 1
- Precautionary statements
- P202-P261-P273-P302+P352-P305+P351+P338-P308+P313
- Hazardous Substances Data
- 142-64-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used to manufacture fibers, pharmaceuticals, and insecticides; [ACGIH] Used as a veterinary anthelmintic medication and a curing agent for polychloroprene; [HSDB]
Plastic Composites Manufacturing [Category: Industry]
MEDICATION (VET)
MEDICATION
CHEM INT FOR ANTIHISTAMINES
USED IN MAKING INSECTICIDES & FIBERS
U.S. Production
(1972) 8.3X10+8 GRAMS
(1975) 7.14X10+8 GRAMS
Formulations/Preparations
PIPERAZINE DIHYDROCHLORIDE 53% BASE /IS/ POPULAR IN DRY FEED OR DRINKING WATER /ANTHELMINTIC/ MEDICATION.
PIPERTAB 2: COMPOSITION: EACH TABLET CONTAINS: PIPERAZINE DIHYDROCHLORIDE EQUIVALENT TO 50 MG PIPERAZINE BASE. ... AVAILABLE IN 500 TABLET BOTTLES. PIPERTAB 10: COMPOSITION: EACH TABLET CONTAINS: PIPERAZINE DIHYDROCHLORIDE EQUIVALENT TO 250 MG PIPERAZINE BASE.
52% piperazine base grades
General Manufacturing Information
Piperazine, hydrochloride (1:2): ACTIVE
INTRODUCED IN 1956 BY THE DOW CHEMICAL COMPANY AS A LIVESTOCK AND POULTRY ANTHELMINTIC.
Applications
UsesIt is used as a one day wormer, either in water or feed, for the control of Round worms in poultry, swine, and horses. It also controls nodular worms in swine, and small strongyles in horses.
UsesIn the manufacture of fibers, pharmarceuticals, and insecticides.
UsesPiperazine Dihydrochloride is an anthelmintic agent used in the treatment of parasitic worms in animals.
General DescriptionWhite to cream-colored needles or powder. Mp: 318-20°C (with decomposition).
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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