PRODUCTS

HEXAHYDROPYRAZINE

Hexahydropyrazine is primarily used as an anthelmintic agent for the treatment of intestinal parasitic worm infections, especially ascariasis (roundworms) and enterobiasis (pinworms) in both humans and animals.
In the chemical industry, Hexahydropyrazine is used to produce epoxy hardeners, polyamide resins, corrosion inhibitors, and as a reagent in CO₂ scrubbing systems (amine gas capture).
Additionally, Hexahydropyrazine serves as a versatile building block in the pharmaceutical industry for the synthesis of various drugs, including antipsychotics, antihistamines, and antidepressants.

CAS Number: 110-85-0
EC Number: 203-808-3
Molecular Formula: C4H10N2
Molecular Weight: 86.14 g/mol

Synonyms: Piperazine, Hexahydropyrazine, Piperazidine, Diethylenediamine, 1,4‑Diazinane, piperazine, 110-85-0, Diethylenediamine, 1,4-Diazacyclohexane, Piperazin, Hexahydropyrazine, Piperazidine, Antiren, 1,4-Piperazine, Diethyleneimine, Pipersol, Eraverm, Dispermine, Lumbrical, Wurmirazin, Uvilon, Piperazine, anhydrous, Worm-A-Ton, 1,4-Diethylenediamine, Pyrazine hexahydride, Hexahydro-1,4-diazine, Pyrazine, hexahydro-, Piperazine (USP), 1RTM4PAL0V, Piperazine [USP], 1,4 Diazacyclohexane, DTXSID1021164, CHEBI:28568, NSC-474, DTXCID701164, FEMA NO. 4250, P02CB01, Vermizine, 1,4 Piperazine, piperazine phosphate (1:1), Ascalix, Ectodyne, Expelix, Wormex, Ins umuline rapide, 203-808-3, Vermex, Asca-Trol No. 3, MFCD00005953, Vermizine (TN), NSC 474, NSC474, Piperazine anhydrous, Eraverm (VAN), Piperazin [German], NCGC00094762-03, Upixon, Piperazin [Germany], CAS-110-85-0, PZE, CCRIS 5950, HSDB 1093, EINECS 203-808-3, UNII-1RTM4PAL0V, UN2579, BRN 0102555, piperizine, piperzine, piprazine, exahydropyrazine, Piperazine-, 7-piperazine, 4-diazacyclohexane, Piperazine,anhydrous, Piperazine, 99%, Tasnon (Salt/Mix), PIPERAZINUM, Exelmin (Salt/Mix), Vermidol (Salt/Mix), Piperazine - anhydrous, Vermizine (Salt/Mix), Spectrum_001113, PIPERAZINE [II], PIPERAZINE [MI], Spectrum5_001817, PIPERAZINE [FHFI], PIPERAZINE [HSDB], SCHEMBL238, WLN: T6M DMTJ, PIPERAZINE [VANDF], PIPERAZINUM [HPUS], EC 203-808-3, PIPERAZINE [MART.], SCHEMBL1640, SCHEMBL8372, Piperazine, p.a., 98%, Trimetazidine EP Impurity G, CHEMBL1412, NCIOpen2_000984, NCIOpen2_000988, NCIOpen2_001024, NCIOpen2_001031, NCIOpen2_001033, NCIOpen2_001071, NCIOpen2_001073, NCIOpen2_001111, NCIOpen2_001151, NCIOpen2_001231, NCIOpen2_001262, NCIOpen2_001269, NCIOpen2_004830, NCIOpen2_004834, NCIOpen2_004862, NCIOpen2_004874, NCIOpen2_004904, NCIOpen2_004910, NCIOpen2_004914, NCIOpen2_004942, NCIOpen2_004952, NCIOpen2_004954, NCIOpen2_004982, NCIOpen2_004992, NCIOpen2_004994, NCIOpen2_005022, NCIOpen2_005032, NCIOpen2_005034, NCIOpen2_005062, NCIOpen2_005072, NCIOpen2_005102, NCIOpen2_005108, NCIOpen2_005145, NCIOpen2_005182, NCIOpen2_005185, NCIOpen2_005187, NCIOpen2_005200, NCIOpen2_005575, NCIOpen2_005980, NCIOpen2_009422, PIPERAZINE [USP-RS], PIPERAZINE [WHO-DD], SCHEMBL77543, KBioSS_001593, 5-23-01-00030 (Beilstein Handbook Reference), BIDD:GT0273, DivK1c_000038, SCHEMBL215254, SCHEMBL524620, SCHEMBL524861, SCHEMBL908308, SPECTRUM1500490, Piperazine, analytical standard, orb1182253, orb2893579, SCHEMBL1663725, SCHEMBL6239923, SCHEMBL6575336, SCHEMBL8010246, PIPERAZINE [GREEN BOOK], HMS500B20, KBio1_000038, KBio2_001593, KBio2_004161, KBio2_006729, MSK7186, NINDS_000038, HMS1920H20, HMS2092A03, HMS3885L08, Pharmakon1600-01500490, PIPERAZINE [USP MONOGRAPH], BCP24060, HY-B0912, Piperazine, ReagentPlus(R), 99%, STR00051, Tox21_113564, Tox21_202242, Tox21_300104, NSC757283, s4574, STL169348, Piperazine [UN2579] [Corrosive], AKOS000269028, CCG-212753, CS-4381, DB00592, FP31694, LF-0561, NSC-757283, UN 2579, IDI1_000038, NCGC00094762-01, NCGC00094762-02, NCGC00094762-04, NCGC00094762-05, NCGC00094762-08, NCGC00254077-01, NCGC00259791-01, Piperazine, anhydrous, >=99.0% (T), BP-31252, SBI-0051485.P003, NS00008207, P0446, P0447, EN300-33920, C07973, D00807, AB00052073_03, Piperazine, BioUltra, anhydrous, >=99.0% (T), Q409292, SR-05000001700, SR-05000001700-1, BRD-K13249881-001-02-3, F0001-0226, Z1245537944, InChI=1/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H, Piperazine, United States Pharmacopeia (USP) Reference Standard, TRIMETAZIDINE DIHYDROCHLORIDE IMPURITY G [EP IMPURITY], 31977-51-2, 1,4-Diazacyclohexane, Hexahydropyrazine, Piperazidine, Diethylenediamine, 1,4-Diazinane, Hexahydropyrazine, Antiren, Diethylenediamine, Diethyleneimine, Dispermine, Eraverm, Lumbrical, Piperazidine, Pipersol, Pyrazine hexahydride, Pyrazine, hexahydro-, Uvilon, Worm-A-Ton, Wurmirazin, 1,4-Diazacyclohexane, 1,4-Piperazine, 1,4-Diethylenediamine, Hexahydro-1,4-diazine, Piperazine, anhydrous, Asca-Trol No. 3, Piperazin, UN 2579, Vermex, Upixon, NSC 474, Diethylenediamine, Diethyleneimine, Dispermine, Antiren, Hexahydropyrazine, Piperazidine, Pipersol, Pyrazine hexahydride, Uvilon, 1,4-
Diazacyclohexane, 1,4-Piperazine, 1,4-Diethylenediamine, Piperazin (German), N,NDiethylenediamine, Hexahydro-1,4-diazine, Piperazidine, Pyrazine hexahydrate, Piperazin, (German), Piperazina (Spanish), Pipérazine (French), Other RN: 8017-90-1, 8027-81-4, 81546-15-8, 854880-15-2, 861800-35-3

Hexahydropyrazine is used to produce epoxy hardeners, polyamide resins, corrosion inhibitors, and as a reagent in CO2 scrubbing (amine gas capture) systems.
Hexahydropyrazine is historically used as an antiparasitic agent in veterinary medicine; a human-use drug is no longer marketed in many regions.
Hexahydropyrazine is included in coatings, adhesives, and flooring materials; sometimes used as flavoring agent internationally.

Hexahydropyrazine is an organic compound with the formula (CH2CH2NH)2.
In term of its structure, Hexahydropyrazine can be described as cyclohexane with the 1- and 4-CH2 groups replaced by NH.

Hexahydropyrazine exists as deliquescent solid with a saline taste.
Hexahydropyrazine is freely soluble in water and ethylene glycol, but poorly soluble in diethyl ether.

Hexahydropyrazine is commonly available industrially is as the hexahydrate, (CH2CH2NH)2·6H2O, which melts at 44 °C and boils at 125–130 °C.
Substituted derivatives of Hexahydropyrazine are a broad class of chemical compounds.

Many Hexahydropyrazines have useful pharmacological properties, prominent examples include viagra, ciprofloxacin, and ziprasidone.
Hexahydropyrazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms.
First used as a solvent for uric acid, the use of Hexahydropyrazine as an anthelmintic agent was first introduced in 1953.

Upon entry into the systemic circulation, the drug is partly oxidized and partly eliminated as an unchanged compound.
Outside the body, Hexahydropyrazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful.

Hexahydropyrazine was first introduced as an anthelmintic in 1953.
Hexahydropyrazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism.

Hexahydropyrazine is needle-like white or colorless crystals.
Hexahydropyrazine is shipped as a solid or suspended in a liquid medium.

Flash point of Hexahydropyrazine is 190 °F.
Hexahydropyrazine is used as a corrosion inhibitor and as an insecticide.

Hexahydropyrazine is an azacycloalkane that consists of a six-membered ring containing two nitrogen atoms at opposite positions.
Hexahydropyrazine has a role as an anthelminthic drug.

Hexahydropyrazine is a saturated organic heteromonocyclic parent, an azacycloalkane and a member of Hexahydropyrazines.
Hexahydropyrazine is a conjugate base of a piperazinium(2+).

Hexahydropyrazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms.
First used as a solvent for uric acid, the use of Hexahydropyrazine as an anthelmintic agent was first introduced in 1953.
Upon entry into the systemic circulation, the drug is partly oxidized and partly eliminated as an unchanged compound.

Outside the body, Hexahydropyrazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful.
Hexahydropyrazine was first introduced as an anthelmintic in 1953.

Hexahydropyrazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism.
Hexahydropyrazine is a cyclic organic compound possessing two nitrogen atoms in opposite positions within a 6-member heterocyclic ring that serves as a backbone for Hexahydropyrazine derivatives and acts as a gamma-amino-butyric acid (GABA) receptor agonist in nematodes, with potential anti-helminthic activity.

Upon administration, Hexahydropyrazine binds to the GABA inhibitory receptors in susceptible nematodes, thereby inducing chloride channel opening and hyperpolarization.
This results in paralysis of the worm musculature and allows normal peristalsis to dislodge the worm from the intestinal lumen, which causes the worm to be expelled from the body.

Unlike vertebrates where GABA is restricted to the central nervous system (CNS), the GABA receptors in helminths are also expressed in the peripheral nervous system.
Hexahydropyrazine belongs to the family of medicines called anthelmintics.

Anthelmintics are used in the treatment of worm infections.
Hexahydropyrazine is used to treat common roundworms (ascariasis) and pinworms (enterobiasis; oxyuriasis).

Hexahydropyrazine works by paralyzing the worms.
They are then passed in the stool.

Hexahydropyrazine is available only with your doctor's prescription.
Hexahydropyrazine is no longer available in the United States.

Hexahydropyrazine is only effective against the adult large roundworm.
Hexahydropyrazine has no effect on any other species of worms, including tapeworms.

Hexahydropyrazine is used to treat different parasitic infections (worm infections) in adults and children.
Parasitic infections are diseases caused by parasites (micro-organisms) that live in or on another host/organism.

Hexahydropyrazine is mainly used in treating infections of the roundworms and pinworms caused by parasites.
Hexahydropyrazine contains it as an active ingredient, which belongs to the class of GABA receptor agonist drugs.

Hexahydropyrazine works by binding to the GABA receptors and causing paralysis of susceptible parasites.
Thus, Hexahydropyrazine treats the infection.

Hexahydropyrazine is a six-sided organic ring compound containing two opposing nitrogen atoms (see image).
The Hexahydropyrazines are a broad class of chemical compounds, all of which contain a Hexahydropyrazine functional group.

Hexahydropyrazines were originally named because of their chemical similarity with piperidine, a constiuent of piperine in the black pepper plant (Piper nigrum).
This has led to the erroneous belief that Hexahydropyrazines are naturally derived from black pepper.

In reality, no Hexahydropyrazines occur naturally; they are usually artificially synthesized by reacting alcoholic ammonia with 1,2-dichloroethane.
Many Hexahydropyrazines are successful drugs

Uses of Hexahydropyrazine:
Hexahydropyrazine is primarily used as an anthelmintic agent for the treatment of intestinal parasitic worm infections, especially ascariasis (roundworms) and enterobiasis (pinworms) in both humans and animals.
In the pharmaceutical industry, Hexahydropyrazine serves as a building block for synthesizing various drugs, including antipsychotics, antihistamines, and antidepressants.

Additionally, Hexahydropyrazine is widely used in the chemical industry as an intermediate in the production of polymers, resins, corrosion inhibitors, and plasticizers.
Hexahydropyrazine also plays a role in carbon capture technologies, where Hexahydropyrazine-based solvents are used to absorb CO₂ from industrial emissions.

Hexahydropyrazine is a cyclic diamine widely employed in multiple industrial and pharmaceutical contexts:

Chemical intermediate:
Hexahydropyrazine is used to produce epoxy hardeners, polyamide resins, corrosion inhibitors, and as a reagent in CO2 scrubbing (amine gas capture) systems.

Pharmaceutical role:
Hexahydropyrazine is historically used as an antiparasitic agent in veterinary medicine; a human-use drug is no longer marketed in many regions.

Other applications:
Hexahydropyrazine is included in coatings, adhesives, and flooring materials; sometimes used as flavoring agent internationally.
Hexahydropyrazine is a small molecule drug with a maximum clinical trial phase of IV and is indicated for helminthiasis.

Hexahydropyrazine was withdrawn in at least one region.
Hexahydropyrazine is an anti-nematodal agent effective against the intestinal nematodes ASCARIS LUMBRICOIDES (roundworm) and ENTEROBIUS VERMICULARIS (pinworm, threadworm).
Hexahydropyrazine produces a neuromuscular block leading to flaccid muscle paralysis in susceptible worms, which are then dislodged from the gut and expelled in feces.

Hexahydropyrazine is used as an anthelmintic:
Hexahydropyrazine was marketed by Bayer as an anthelmintic in the early 20th century, and was featured in print ads alongside other popular Bayer products at the time, including heroin.

In fact, a large number of Hexahydropyrazine compounds have an anthelmintic action.
Their mode of action is generally by paralysing parasites, which allows the host body to easily expel the invasive organism.

The neuromuscular effects are thought to be caused by blocking acetylcholine at the myoneural junction.
This action is mediated by Hexahydropyrazine's agonist effects upon the inhibitory GABA (γ-aminobutyric acid) receptor.

Hexahydropyrazine's selectivity for helminths is because vertebrates use GABA only in the CNS, and the GABA receptor of helminths is of a different isoform from that of vertebrates.
Hexahydropyrazine hydrate, Hexahydropyrazine adipate and Hexahydropyrazine citrate (used to treat ascariasis and enterobiasis) are the most common anthelmintic Hexahydropyrazine compounds.

These drugs are often referred to simply as "Hexahydropyrazine" which may cause confusion between the specific anthelmintic drugs, the entire class of Hexahydropyrazine-containing compounds, and the compound itself.
Two common salts in the form of which Hexahydropyrazine is usually prepared for pharmaceutical or veterinary purposes are the citrate, 3C4H10N2·2C6H8O7 (i.e. containing 3 molecules of Hexahydropyrazine to 2 molecules of citric acid), and the adipate, C4H10N2·C6H10O4 (containing 1 molecule each of Hexahydropyrazine and adipic acid)

Hexahydropyrazine Uses in Medicine Field:
Hexahydropyrazine belongs to the anthelmintics medicine family.
These anthelmintics medicines are mainly used for the treatment of worm infections.

These include the infections caused by common roundworms like ascariasis and pinworms like enterobiasis and oxyuriasis.
When the Hexahydropyrazine enters the human body, it starts work to paralyze the worms and it will dispose of in the stool.

The dosage of Hexahydropyrazine should be determined by the physician.
Hexahydropyrazine is a medication used to treat worm infections caused by roundworms or pinworms.

Hexahydropyrazine is available in lozenges, powder, and syrup forms, available without a prescription.
Hexahydropyrazine belongs to the class of anthelmintic medications.

This medication works by paralyzing worms in the digestive tract.
This prevents the worms from multiplying in the intestines and is excreted in the stool.

Hexahydropyrazine is a large class of chemical compounds which all have a common Hexahydropyrazine function group in their structure.
Hexahydropyrazine is also an anthelmintic; anthelmintics are used in the treatment of worm infections.
Although Hexahydropyrazine for human use has been discontinued, they may still be used for worm treatment in animals.

Benefits of Hexahydropyrazine:

Medicinal Benefits:
Hexahydropyrazine contains it as an active ingredient, which belongs to the class of GABA receptor agonist drugs.
Hexahydropyrazine works by binding to the muscle membrane of GABA receptors.
This causes paralyzing of the worms and eventually leads to the death of susceptible helminths and thus prevents the growth of parasitic infections.

Action Mechanism of Hexahydropyrazine:
Hexahydropyrazine is a medication that has garnered significant attention due to its usage in treating parasitic worm infections.
The mechanism of action of Hexahydropyrazine primarily revolves around its ability to paralyze parasites, facilitating their expulsion from the host's body.

To delve deeper into the specifics, Hexahydropyrazine is essential to understand the pharmacodynamics and pharmacokinetics of this compound.
Primarily, Hexahydropyrazine targets the neuromuscular system of parasitic worms, particularly nematodes.

The drug exerts Hexahydropyrazine's effect by mimicking the action of gamma-aminobutyric acid (GABA), a neurotransmitter that inhibits neuronal activity in these parasites.
GABA usually acts on GABA receptors, which are chloride ion channels, leading to hyperpolarization and subsequent relaxation of the muscle.

Hexahydropyrazine enhances the effect of GABA at these sites, causing an increased influx of chloride ions into the muscle cells.
As a result, the muscle cells become hyperpolarized, leading to muscle relaxation and paralysis of the worm.

Once paralyzed, the worms lose their grip on the intestinal wall and are expelled from the body through peristalsis, the natural movement of the digestive tract.
This expulsion is assisted by the normal bowel movements of the host, effectively clearing the infection without causing significant harm to the intestinal lining or inciting severe inflammatory responses.

Pharmacokinetically, Hexahydropyrazine is absorbed rapidly when taken orally and distributed throughout the body's tissues.
Hexahydropyrazine is metabolized primarily in the liver, where it undergoes various biochemical transformations.
The metabolites, along with a fraction of unchanged Hexahydropyrazine, are then excreted through the kidneys.

Due to this excretion route, caution is advised in patients with renal impairment, as accumulation of the drug could potentially lead to toxicity.
One of the notable advantages of Hexahydropyrazine is its relatively low toxicity to humans.

However, Hexahydropyrazine is essential to adhere to prescribed dosages and duration of treatment to avoid potential side effects, which may include nausea, vomiting, diarrhea, and, in rare cases, neurological symptoms such as dizziness and tremors.

These side effects are generally mild and transient, resolving upon discontinuation of the drug.
Hexahydropyrazine's effectiveness against a variety of parasitic worms, coupled with its relatively benign side effect profile, has made it a valuable tool in the fight against parasitic infections.

Hexahydropyrazine's mechanism of action, focusing on the neuromuscular paralysis of worms, sets it apart from other antiparasitic agents, offering a unique approach to managing and eliminating these infections.
Understanding the pharmacodynamics and pharmacokinetics of Hexahydropyrazine not only highlights its therapeutic potential but also underscores the importance of proper usage to maximize benefits and minimize risks.

Origin of Hexahydropyrazine:
Hexahydropyrazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (Piper nigrum).
The -az- infix added to "Hexahydropyrazine" refers to the extra nitrogen atom, compared to piperidine.
Hexahydropyrazine is important to note, however, that Hexahydropyrazines are not derived from plants in the Piper genus.

Synthesis and Structure of Hexahydropyrazine:
Hexahydropyrazine is formed by the ammoniation of 1,2-dichloroethane or ethanolamine.
This reaction is mainly used for production of ethylene diamine, but Hexahydropyrazine is a side product.

The Hexahydropyrazine is separated from the product stream, which, in addition to ethylenediamine, also contains various derivatives containing CH2CH2NH subunits, e.g. diethylenetriamine, aminoethylHexahydropyrazine, and other related linear and cyclic chemicals of this type.
Hexahydropyrazine can also be synthesized by reduction of pyrazine with sodium in ethanol.

As confirmed by X-ray crystallography, piperidine is a centrosymmetric molecule.
The ring adopts a chair conformation and the two N-H groups are equatorial.

Reactions of Hexahydropyrazine:
Hexahydropyrazine's basicity is that of a typical amine.
The pH of a 10% aqueous solution of Hexahydropyrazine is 10.8–11.8.
The two pKb's are 5.35 and 9.73 at 25 °C.

Hexahydropyrazine readily absorbs water and carbon dioxide from the air.
Carbon dioxide produce a series of carbamates.

Some of the relevant equilibria are:
HN(CH2CH2)2NH + CO2 ⇌ H2N+(CH2CH2)2NCO−2

2 HN(CH2CH2)2NH + CO2 ⇌ HN(CH2CH2)2NCO−2 + HN(CH2CH2)2NH+2
H2N+(CH2CH2)2NCO−2 + CO2 ⇌ HO2CN(CH2CH2)2NCO2H

As a basic amine, Hexahydropyrazine forms a variety of coordination complexes, usually binding to metals as a unidentate ligand (bidentate binding would require the boat conformation).

One example is the polymer [CoCl2(Hexahydropyrazine)]n, which features tetrahedral cobalt centers linked by bridging Hexahydropyrazine ligands.
Hexahydropyrazine is easily N-alkylated.
Depending on conditions mono- or dialkyl derivatives are obtained

Chemical Structure and Biological Applications of Hexahydropyrazine:
The chemical structure of Hexahydropyrazine is C₄H₁₀N₂.
Hexahydropyrazine is the organic compound, which is consist of six membrane ring with the presence of two opposite nitrogen atom.

Hexahydropyrazine is an anthelmintic drug and they are mainly used for the treatment of intestinal roundworm infections in domestic animals and human beings and also can treat pinworm infections in human beings.

The physician usually suggests Hexahydropyrazine citrate for treating disease.
The intake of Hexahydropyrazine will act on the worms and they are paralyzed and eliminated through the stool.

Chemical Structure of Hexahydropyrazine:
Hexahydropyrazine can be freely soluble in ethylene glycol and water.
But they remain insoluble in diethyl ether.
Hexahydropyrazine is a weak base component, which has two pKbs of 5.35 and 9.73 at 25 °C.

The 10% of Hexahydropyrazine present in the aqueous solution will have a pH between 10.8–11.8.
Hexahydropyrazine can absorb carbon dioxide and water from the air.

Many Hexahydropyrazines are occurring in nature in various forms.
Also, Hexahydropyrazine can synthesize by reacting alcoholic ammonia with 1,2-dichloroethane or by the action of ethylene glycol and sodium on ethylene diamine hydrochloride or by reducing pyrazine with the presence of sodium in ethanol.

A form of Hexahydropyrazine is commonly available in industries in the form of hexahydrate C₄H₁₀N₂·6H₂O.
The Hexahydropyrazine used in industries has a melting point of 44 °C and it can boil at 125–130 °C.
Usually, Hexahydropyrazine is available in the form of two common salts.

The Hexahydropyrazine citrate uses are predominant for pharmaceutical and veterinary purposes.
The chemical structure of citrate of Hexahydropyrazine is 3C₄H₁₀N₂·2C₆H₈O₇.

Citrate contains 3 molecules of Hexahydropyrazine to 2 molecules of citric acid.
The chemical structure of adipate is C₄H₁₀N₂·C₆H₁₀O₄.

Adipate contains 1 molecule of Hexahydropyrazine and adipic acid.
Hexahydropyrazine can synthesize with the co-product of the ammoniation of 1,2-dichloroethane or ethanolamine.

These are the only routes for the using in commercial industries.
The Hexahydropyrazine are usually separated from the product stream, which contains, ethylenediamine, diethylenetriamine, and other related cyclic and linear chemicals.

Hexahydropyrazine Derivatives as Drugs:
Many notable drugs contain a Hexahydropyrazine ring as part of their molecular structure.
They may be used as antiparasitic drugs.

Other examples include:
Diethylcarbamazine, a derivative of Hexahydropyrazine, is used to treat some types of filariasis.
Most of these agents can be classified as either phenylHexahydropyrazines, benzylHexahydropyrazines, diphenylmethylHexahydropyrazines (benzhydrylHexahydropyrazines), pyridinylHexahydropyrazines, pyrimidinylHexahydropyrazines, or tricyclics (with the Hexahydropyrazine ring attached to the heterocyclic moiety via a side chain).

Hexahydropyrazine is also a fluid used for CO2 and H2S scrubbing in association with methyl diethanolamine (MDEA).
Hexahydropyrazine belongs to the family of medicines called anthelmintics.
Anthelmintics are used in the treatment of worm infections.

Hexahydropyrazine is used to treat:
common roundworms (ascariasis) and pinworms (enterobiasis; oxyuriasis).

Hexahydropyrazine works by paralyzing the worms.
They are then passed in the stool.

Hexahydropyrazine is available only with your doctor's prescription.
Hexahydropyrazine, anthelmintic drug used in the treatment of intestinal roundworm infection in humans and domestic animals (including poultry) and against pinworm infection in humans.

Hexahydropyrazine is administered orally, in repeated doses, usually as the citrate salt.
Hexahydropyrazine's action causes worms to be paralyzed and then eliminated in the stool.
Hexahydropyrazine app. 68% is an aqueous solution of a cyclic amine with various applications.

Hexahydropyrazine Chips:
Hexahydropyrazine chips are used mainly as a building block for medical drugs and in the synthesis of polyamides and urethane systems.
In addition, Hexahydropyrazine chips serve as an intermediate for epoxy systems.

Hexahydropyrazine is an anthelmintic with activity against nematodes.
Hexahydropyrazine induces a reversible flaccid paralysis in the nematode parasites.

This is provoked by hyperpolarisation of the cell membrane followed by suppression of spontaneous spike potentials.
The paralysed nematodes are subsequently expelled from the gut lumen by normal peristaltic actions.

Indications:
Nematode infections in horses, cattle, swine and poultry.

Horses:
Strongylosis spp., Oxyurosis spp., Trichonema spp. and Ascaris spp.

Cattle:
Ascaris spp., Nematodirus spp., Ostertagia spp., Cooperia spp. and Oesophagostomum spp.

Swine:
Oesophagostomum spp. and Ascaris spp.

Poultry:
Ascaris spp. and Capillaria spp.

Hexahydropyrazines have been described as ‘failed pharmaceuticals’, as some had been evaluated as potential therapeutic agents by pharmaceutical companies but never brought to the market.

One Hexahydropyrazine that has been commonly used as NPS is 1-benzylHexahydropyrazine (BZP) though other Hexahydropyrazine derivatives have also been reported.
These include among others 1-(3-chlorophenyl) Hexahydropyrazine (mCPP), 1-(3-trifluoromethylphenyl) Hexahydropyrazines (TFMPP), 1-benzyl-4-methylHexahydropyrazine (MBZP), 1-(4-fluorophenyl) Hexahydropyrazines (pFPP) and 1-cyclohexyl-4-(1,2-diphenylethyl) Hexahydropyrazine (MT-45).

Handling and Storage of Hexahydropyrazine:

Handling:
Use in a well-ventilated area or fume hood.
Avoid contact with skin, eyes, and clothing.

Prevent inhalation of dust or vapor.
Wash hands thoroughly after handling.
Do not eat, drink, or smoke while using this product.

Storage:
Store in a tightly closed container.
Keep in a cool, dry, well-ventilated place.

Keep away from oxidizing agents, acids, and moisture.
Recommended storage temperature: 2–8°C.

Stability and Reactivity of Hexahydropyrazine:

Chemical Stability:
Stable under recommended storage conditions.

Incompatible Materials:
Strong oxidizers (e.g., hydrogen peroxide).
Acids and acid chlorides.
Carbon dioxide and carbon disulfide (may react vigorously).

Hazardous Decomposition Products:
Nitrogen oxides (NOₓ), carbon monoxide (CO), carbon dioxide (CO₂), and ammonia.

Conditions to Avoid:
Excessive heat, sparks, open flames.
Moisture and exposure to air (may lead to degradation).

First Aid Measures of Hexahydropyrazine:

Inhalation:
Move person to fresh air.
If breathing is difficult, give oxygen.
Seek medical attention if symptoms persist.

Skin Contact:
Immediately wash with plenty of water and soap.
Remove contaminated clothing.
Seek medical attention for persistent irritation.

Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Lift eyelids to ensure thorough rinsing.
Seek immediate medical attention.

Ingestion:
Do not induce vomiting.
Rinse mouth with water.
Seek medical attention immediately.

Firefighting Measures of Hexahydropyrazine:

Suitable Extinguishing Media:
Dry chemical, carbon dioxide, water spray, or alcohol-resistant foam.

Specific Hazards:
May release toxic fumes (e.g., NOₓ, CO, CO₂) when burned.

Protective Equipment for Firefighters:
Full protective clothing and self-contained breathing apparatus (SCBA).

Accidental Release Measures of Hexahydropyrazine:

Personal Precautions:
Wear appropriate PPE (gloves, goggles, mask).
Avoid dust formation and inhalation.

Environmental Precautions:
Prevent further leakage or spillage if safe.
Do not allow to enter drains or watercourses.

Cleanup Methods:
Sweep up or vacuum material and place in a suitable container for disposal.
Ventilate area and wash spill site after cleanup.

Exposure Controls / Personal Protection of Hexahydropyrazine:

Engineering Controls:
Use local exhaust ventilation to minimize exposure.
Ensure eye wash stations and safety showers are accessible.

Personal Protective Equipment (PPE):

Eye/Face Protection:
Chemical safety goggles.

Skin Protection:
Nitrile or neoprene gloves, lab coat.

Respiratory Protection:
Use NIOSH-approved respirator if dust/vapor is present.

Body Protection:
Wear suitable protective clothing.

Occupational Exposure Limits:
TLV (ACGIH): 10 ppm (skin)

MAK (Germany): 1 ppm

Identifiers of Hexahydropyrazine:
Molecular Formula: C₄H₁₀N₂
Molecular Weight: 86.14 g/mol
CAS Number: 110-85-0
EC Number (EINECS): 203-808-3
UN Number: 2579 (for transportation of Hexahydropyrazine solid)
PubChem CID: 31252
ChEBI ID: CHEBI:18153
ChemSpider ID: 28994
InChI: InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
InChI Key: JLAZFGKZLGGHSS-UHFFFAOYSA-N
SMILES: N1CCNCC1
RTECS Number: TK7875000

CAS Number: 110-85-0
EC Number: 203-808-3
UN Number: 2579
PubChem CID: 31252
ChEMBL ID: CHEMBL511
ChEBI ID: CHEBI:18153
ChemSpider ID: 28994
RTECS Number: TK7875000
UNII (FDA): 63X7MBT2RV
NSC Number: 1018
KEGG Compound ID: C06590
Beilstein Registry: 1716564

SMILES: N1CCNCC1
InChI: InChI=1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
InChIKey: JLAZFGKZLGGHSS-UHFFFAOYSA-N

Properties of Hexahydropyrazine:
Appearance: White to colorless crystalline solid or needles; deliquescent and absorbs moisture/CO₂ from air
Odor & Taste: Ammoniacal, acrid odor; tastes saline
Density / Specific Gravity: ~1.1g/cm³ (solid)
Melting Point: ~106°C (anhydrous); hexahydrate melts at ~44°C
Boiling Point: ~146°C (sublimes)
Water Solubility: Very high – ~150,000mg/L at 20–25°C
LogKₒw: –1.24 (hydrophilic)
pKₐ Values: ~9.7 and ~5.3 (primary and secondary amines)
Vapor Pressure: ~39Pa at 20°C
Hygroscopicity: Strong; absorbs CO₂ and water, forming carbamates and hydrates

Molecular Formula: C4H10N2
Molecular Weight: 86.14 g/mol
XLogP3: -1.5
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 86.084398327 Da
Monoisotopic Mass: 86.084398327 Da
Topological Polar Surface Area: 24.1 Å²
Complexity: 26.5
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Basicity (pKb): 4.19
Magnetic susceptibility (χ): −56.8·10−6 cm3/mol
Empirical Formula (Hill Notation): C4H10N2
CAS Number: 110-85-0
Molecular Weight: 86.14
Beilstein: 102555
EC Number: 203-808-3
MDL number: MFCD00005953
UNSPSC Code: 12352100

Decomposition temperature: No data available
pH: 12 at 150 g/l at 20 °C
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility: ca.0.9 g/l at 20 °C - soluble
Partition coefficient: n-octanol/water log Pow: -1.24 at 25 °C - Bioaccumulation is not expected.
Vapor pressure: 0.21 hPa at 20 °C

Density: 1.1 g/cm3 at 20 °C
Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: Not classified as explosive.
Oxidizing properties: none
Other safety information: No data available