Substituted piperazines are a class of

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

s based on a

piperazine Piperazine () is an organic compound with the formula . In term of its structure, it can be described as cyclohexane with the 1- and 4-CH2 groups replaced by NH. Piperazine exists as deliquescent solid with a saline taste. Piperazine is freely sol ...

core. Some are used as

recreational drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...

s and some are used in

scientific research The scientific method is an empirical method for acquiring knowledge that has been referred to while doing science since at least the 17th century. Historically, it was developed through the centuries from the ancient and medieval world. The ...

List of substituted piperazines

Benzylpiperazines

File:Benzylpiperazine.svg, 1-Benzylpiperazine (BZP) File:Methylbenzylpiperazine.svg, 1-Methyl-4-benzylpiperazine (MBZP) File:DBZP.svg, 1,4-Dibenzylpiperazine (DBZP) File:MDBZP.svg, 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP) File:2C-B-BZP.svg,

4-Bromo-2,5-dimethoxy-1-benzylpiperazine 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". It produces stimulant effects similar to those of benzylpiperazine (BZP). ...

(2C-B-BZP) File:Methoxypiperamide.png,

Methoxypiperamide Methoxypiperamide (also known as MeOP and MEXP) is a psychoactive drug of the piperazine class that has been sold online as a designer drug. It is the 4-methoxy-α-keto analog of methylbenzylpiperazine. Very little data exists about the pharma ...

(MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone) File:Sunifiram.svg ,

Sunifiram Sunifiram (developmental code name DM-235) is an experimental drug which has antiamnesic effects in animal studies and with significantly higher potency than piracetam. Sunifiram is a molecular simplification of unifiram (DM-232). Another analo ...

(1-benzoyl-4-propanoylpiperazine) File:3-Methylbenzylpiperazine structure.png,

3-Methylbenzylpiperazine 3-Methylbenzylpiperazine (3-Me-BZP) is a stimulant drug which is a derivative of benzylpiperazine. It has been sold as a designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to ...

(3-MeBZP) File:Befuraline.svg,

Befuraline Befuraline (DIV-154) is a psychoactive drug and member of the piperazine chemical class which was drug development, developed in Germany in the 1970s. Befuraline has stimulant and antidepressant effects and has seen some use in Germany and Franc ...

(also produces benzylpiperazine as a metabolite) File:Fipexide.svg,

Fipexide Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983. It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia, but is no longer in commo ...

(also produces substituted benzylpiperazine as a metabolite) File:Piberaline.svg,

Piberaline Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzyl ...

(also produces benzylpiperazine as a metabolite)

Phenylpiperazines

''ortho''-Substituted

* 2-Chlorophenylpiperazine (oCPP) * 2-Methylphenylpiperazine (oMPP) * 2-Methoxyphenylpiperazine (oMeOPP) *

Mefeclorazine Mefeclorazine () is a neuroleptic (antipsychotic) of the phenethylamine and arylpiperazine groups. Part of mefeclorazine's chemical structure is based on 3,4-dimethoxyphenethylamine (DMPEA or homoveratrylamine), which has structural similari ...

* Vortioxetine

Enpiprazole Enpiprazole (INN, BAN) is an anxiolytic drug of the phenylpiperazine group that was never marketed. It produces anxiolytic-like effects in animals, though these effects appear to be biphasic and may reverse at high doses. It is known to produce ...

is known to produce oCPP as a metabolite. It was initially anticipated to produce oMeOPP as a metabolite, but this proved not to be the case.

''meta''-Substituted

* 3-Chlorophenylpiperazine (mCPP) * 3-Methoxyphenylpiperazine (mMeOPP) * 3-Trifluoromethylphenylpiperazine (TFMPP) *

1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is a designer drug of the piperazine class of chemical substances. 3C-PEP is related to ''meta''-cholorophenylpiperazine (mCPP) and phenethylamine which can be thought of as mCPP having a ...

(3C-PEP)

Trazodone Trazodone is an antidepressant medication used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken or ...

nefazodone Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant medication which is used in the treatment of depression and for other uses. Nefazodone was withdrawn in most countries by ...

etoperidone Etoperidone, associated with several brand names, is an atypical antidepressant which was developed in the 1970s and either is no longer marketed or was never marketed. It is a phenylpiperazine related to trazodone and nefazodone in chemical s ...

mepiprazole Mepiprazole (INN, BAN) (brand name Psigodal) is an anxiolytic drug of the phenylpiperazine group with additional antidepressant properties that is marketed in Spain. It acts as a 5-HT2A and α1-adrenergic receptor antagonist and inhibits the ...

, and others produce mCPP as a metabolite.

''para''-Substituted

4-Chlorophenylpiperazine ''para''-Chlorophenylpiperazine (pCPP) is a psychoactive drug of the phenylpiperazine class. It is relatively obscure, with limited human use, and produces slightly psychedelic effects. It has been encountered in illicit capsules as a recreation ...

(pCPP) * 4-Fluorophenylpiperazine (pFPP) * 4-Methylphenylpiperazine (pMPP) * 4-Methoxyphenylpiperazine (pMeOPP, MeOPP) * 4-Nitrophenylpiperazine (pNPP; PAL-175) – selective partial serotonin releasing agent * 4-Trifluoromethylphenylpiperazine (pTFMPP)

Multiple substitutions

File:Dichlorophenylpiperazine-ifa.png, 2,3-Dichlorophenylpiperazine (2,3-DCPP) File:3,4-DCPP_structure.svg, 3,4-Dichlorophenylpiperazine (3,4-DCPP) * 2,3-Dimethylphenylpiperazine (DMPP) * 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP; PAL-179) – selective partial serotonin releasing agent

Others

1-Phenylpiperazine 1-Phenylpiperazine (1-PP or PP) is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class. It is a rigid ...

(PP)

Other arylpiperazines

* 1-(1-Naphthyl)piperazine (1-NP) * 1-(2-Pyrimidinyl)piperazine (1-PP) * ORG-12962 (1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine) *

Quipazine Quipazine, also known as 1-(2-quinolinyl)piperazine (2-QP), is a serotonin, serotonergic drug of the arylpiperazine family and an structural analog, analogue of 1-(2-pyridinyl)piperazine which is used in scientific research. It was first describ ...

(2-piperazin-1-ylquinoline) Many

azapirone Azapirones are a class of drugs used as anxiolytics, antidepressants, and antipsychotics. They are commonly used as Augmentation (psychiatry), add-ons to other antidepressants, such as selective serotonin reuptake inhibitors (SSRIs). List of ...

s such as

buspirone Buspirone, sold under the brand name Buspar among others, is an anxiolytic, a medication primarily used to treat anxiety disorders, particularly generalized anxiety disorder (GAD). It is a serotonin 5-HT1A receptor, 5-HT1A receptor partial ag ...

gepirone Gepirone, sold under the brand name Exxua, is a medication used for the treatment of major depressive disorder. It is taken orally. Side effects of gepirone include dizziness, nausea, insomnia, abdominal pain, and dyspepsia (indigestion). Ge ...

, and tandospirone produce 1-PP as a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

By drug class

Antianginal An antianginal is a drug used in the treatment of ''angina pectoris'', a symptom of ischaemic heart disease. Myocardial ischemia arises from the dysfunction of coronary macrovascular or microvascular components, leading to a compromised supply o ...

s * Ranolazine *

Trimetazidine Trimetazidine (IUPAC: 1-(2,3,4-trimethoxybenzyl)piperazine) is a drug sold under many brand names for angina pectoris (chest pain associated with impaired blood flow to the heart). Trimetazidine is described as the first cytoprotective anti-i ...

Antidepressant Antidepressants are a class of medications used to treat major depressive disorder, anxiety disorders, chronic pain, and addiction. Common side effects of antidepressants include Xerostomia, dry mouth, weight gain, dizziness, headaches, akathi ...

s *

Amoxapine Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylation, demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980, approximat ...

Buspirone Buspirone, sold under the brand name Buspar among others, is an anxiolytic, a medication primarily used to treat anxiety disorders, particularly generalized anxiety disorder (GAD). It is a serotonin 5-HT1A receptor, 5-HT1A receptor partial ag ...

* Flesinoxan *

Gepirone Gepirone, sold under the brand name Exxua, is a medication used for the treatment of major depressive disorder. It is taken orally. Side effects of gepirone include dizziness, nausea, insomnia, abdominal pain, and dyspepsia (indigestion). Ge ...

Ipsapirone Ipsapirone is a selective 5-HT1A receptor partial agonist of the piperazine and azapirone chemical classes. It has antidepressant and anxiolytic effects. Ipsapirone was studied in several placebo-controlled trials for depression and continue ...

Nefazodone Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant medication which is used in the treatment of depression and for other uses. Nefazodone was withdrawn in most countries by ...

* Tandospirone *

Vilazodone Vilazodone, sold under the brand name Viibryd among others, is a medication used to treat major depressive disorder. It is classified as a serotonin modulator and is taken by mouth. Common side effects include nausea, diarrhea, and trouble ...

* Vortioxetine * Zalospirone

Antihistamine Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provides ...

s * Buclizine *

Cetirizine Cetirizine is a second-generation antihistamine, second-generation Peripherally selective antihistamine used to treat allergic rhinitis (hay fever), dermatitis, and urticaria (hives). It is taken by mouth. Effects generally begin within thirty ...

* Cinnarizine * Cyclizine *

Hydroxyzine Hydroxyzine, sold under the brand names Atarax and Vistaril among others, is an antihistamine medication. It is used in the treatment of itchiness, anxiety, insomnia, and nausea (including that due to motion sickness). It is used either by mou ...

Levocetirizine Levocetirizine, sold under the brand name Xyzal, among others, is a second-generation antihistamine used for the treatment of allergic rhinitis (hay fever) and long-term hives of unclear cause. It is less sedating than older antihistamines. ...

Meclizine Meclizine, sold under the brand name Bonine, among others, is an antihistamine used to treat motion sickness and dizziness (vertigo). It is taken by mouth. Effects generally begin in an hour and last for up to a day. Common side effects in ...

* Niaprazine Antiserotonergics * EGIS-7625

Antipsychotic Antipsychotics, previously known as neuroleptics and major tranquilizers, are a class of Psychiatric medication, psychotropic medication primarily used to manage psychosis (including delusions, hallucinations, paranoia or disordered thought), p ...

s * Typical **

Flupentixol Flupentixol (INN), also known as flupenthixol (former BAN), marketed under brand names such as Depixol and Fluanxol is a typical antipsychotic drug of the thioxanthene class. It was introduced in 1965 by Lundbeck. In addition to single drug pre ...

Fluphenazine Fluphenazine, sold under the brand name Prolixin among others, is a high-potency typical antipsychotic medication. It is used in the treatment of chronic psychoses such as schizophrenia, and appears to be about equal in effectiveness to low-pot ...

Perphenazine Perphenazine is a typical antipsychotic drug. Chemically, it is classified as a piperazinyl phenothiazine. Originally marketed in the United States as Trilafon, it has been in clinical use for decades. Perphenazine is roughly ten times as pote ...

Prochlorperazine Prochlorperazine, formerly sold under the brand name Compazine among others, is a medication used to treat nausea, migraines, schizophrenia, psychosis and anxiety. It is a less preferred medication for anxiety. It may be taken by mouth, rectal ...

Thiothixene Tiotixene, or thiothixene is a typical antipsychotic agent currently sold under the brand name Navane which is predominantly utilised to treat acute and chronic schizophrenia. Beyond its primary Indication (medicine), indication, it can exhibit ...

Trifluoperazine Trifluoperazine, marketed under the brand name Stelazine among others, is a typical antipsychotic primarily used to treat schizophrenia. It may also be used short term in those with generalized anxiety disorder but is less preferred to benzodiaze ...

Zuclopenthixol Zuclopenthixol (brand names Cisordinol, Clopixol and others), also known as zuclopentixol, is a medication used to treat schizophrenia and other psychoses. It is classed, pharmacologically, as a typical antipsychotic. Chemically it is a thioxant ...

** Acetophenazine ** Carfenazine *

Atypical ''Atypical'' is an American comedy-drama television series created by Robia Rashid for Netflix. The series takes place in Connecticut, and focuses on the life of 18-year-old Samuel "Sam" Gardner ( Keir Gilchrist), who is autistic. The first sea ...

** Amperozide **

Aripiprazole Aripiprazole, sold under the brand name Abilify, among others, is an atypical antipsychotic primarily used in the treatment of schizophrenia, bipolar disorder, and irritability associated with autism spectrum disorder; other uses include as ...

Clozapine Clozapine, sold under the brand name Clozaril among others, is a psychiatric medication and was the first atypical antipsychotic to be discovered. It is used primarily to treat people with schizophrenia and schizoaffective disorder who have ...

Lurasidone Lurasidone, sold under the brand name Latuda among others, is an atypical antipsychotic medication used to treat schizophrenia and bipolar depression. It is taken by mouth. Common side effects include sedation, indigestion, nausea, and inso ...

Olanzapine Olanzapine, sold under the brand name Zyprexa among others, is an atypical antipsychotic primarily used to treat schizophrenia and bipolar disorder. It is also sometimes used off-label for treatment of chemotherapy-induced nausea and vomitin ...

** Perospirone **

Ziprasidone Ziprasidone, sold under the brand name Geodon among others, is an atypical antipsychotic used to treat schizophrenia and bipolar disorder. It may be used by mouth and by injection into a muscle (IM). The intramuscular form may be used for ...

Quetiapine Quetiapine ( ), sold under the brand name Seroquel among others, is an atypical antipsychotic medication used in the treatment of schizophrenia, bipolar disorder, bipolar depression, and major depressive disorder. Despite being widely prescri ...

Cariprazine Cariprazine, sold under the brand name Vraylar among others, is an atypical antipsychotic developed by Gedeon Richter, which is used in the treatment of schizophrenia and bipolar disorder. It is also prescribed as an add-on treatment for bip ...

Recreational Drug Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an Sub ...

s *

(2C-B-BZP) * 1-Benzylpiperazine (BZP) * 2,3-Dichlorophenylpiperazine (DCPP) * 1,4-Dibenzylpiperazine (DBZP) * 4-Methyl-1-benzylpiperazine (MBZP) * 3-Chlorophenylpiperazine (mCPP) * 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP) * 4-Methoxyphenylpiperazine (MeOPP) *

(MeOP or MEXP) *

(pCPP) * 4-Fluorophenylpiperazine (pFPP) * 3-Trifluoromethylphenylpiperazine (TFMPP)

Urological Urology (from Greek οὖρον ''ouron'' "urine" and ''-logia'' "study of"), also known as genitourinary surgery, is the branch of medicine that focuses on surgical and medical diseases of the urinary system and the reproductive organs. Orga ...

s *

Sildenafil Sildenafil, sold under the brand name Viagra among others, is a medication used to treat erectile dysfunction and pulmonary hypertension, pulmonary arterial hypertension. It is also sometimes used off-label for the treatment of certain sym ...

Vardenafil Vardenafil, sold under the brand name Levitra among others, is a medication that is used for treating erectile dysfunction. It is a PDE5 inhibitor. It is taken by mouth. Medical uses Vardenafil's indications and contraindications are the same ...

Others * 6-Nitroquipazine * Antrafenine * Diethylcarbamazine * Diphenazine *

Imatinib Imatinib, sold under the brand names Gleevec and Glivec (both marketed worldwide by Novartis) among others, is an oral targeted therapy medication used to treat cancer. Imatinib is a small molecule inhibitor targeting multiple tyrosine kinases ...

NSI-189 ALTO-100, previously known as NSI-189 (NeuralStem Inc. 189), is a drug described as a hippocampal neurogenesis stimulant and indirect brain-derived neurotrophic factor (BDNF) modulator which is under development for the treatment of major dep ...

Pipobroman Pipobroman (trade names Vercite, Vercyte) is an anti-cancer drug that probably acts as an alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a fre ...

(antineoplastic agent) *

(nootropic) *

Tolpiprazole Tolpiprazole (INN, BAN) (developmental code name H-4170) is an anxiolytic drug of the phenylpiperazine group that was never marketed. See also * Acaprazine * Enpiprazole * Lorpiprazole * Mepiprazole Mepiprazole (INN, BAN) (brand name Ps ...

(tranquilizer)

Activities

References

External links

* {{DEFAULTSORT:Substituted Piperazines Arylpiperazines Benzylamines Chemical classes of psychoactive drugs Designer drugs