Substituted Phenylpiperazine
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Substituted Phenylpiperazine
Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research. 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 (2C-B-BZP) File:Methoxypiperamide.png, Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone) File:Sunifiram.svg , Sunifiram (1-benzoyl-4-propanoylpiperazine) File:3-Methylbenzylpiperazine structure.png, 3-Methylbenzylpiperazine (3-MeBZP) File:Befuraline.svg, Befuraline(also produces benzylpiperazine as a metabolite) File:Fipexide.svg, Fipexide(also produces substituted benzylpiperazine as a metabolite) File:Piberaline.svg, Piberaline(also produces benzylp ...
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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 is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances. In this process, bonds between atoms may be broken or new bonds formed or both. There are four major types of compounds, distinguished by how the constituent atoms are bonded together. Molecular compounds are held together by covalent bonds; ionic compounds are held together by ionic bonds; intermetallic compounds are held together by metallic bonds; coordination complexes are held together by coordinate covalent bonds. Non-stoichiometric compounds form a disputed marginal case. A chemical formula specifies the number of atoms of each element in a compound molecule, usin ...
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OMeOPP
''ortho''-Methoxyphenylpiperazine (oMeOPP), also known as 2-methoxyphenylpiperazine (2-MeOPP), is a phenylpiperazine derivative which is known to act as a serotonergic agent. Along with various other phenylpiperazines, like benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP), oMeOPP has been found in illicit drug samples. Pharmacology The drug has been found to have high affinity for the serotonin 5-HT1A receptor, where it acts as a partial agonist ( ≈ 70%), but shows no affinity for the serotonin 5-HT2 receptor or the dopamine receptors. This is in contrast to the related drug ''meta''-chlorophenylpiperazine (mCPP), which shows high affinity for both the serotonin 5-HT1A and 5-HT2 receptors. oMeOPP and mCPP have both been found to suppress conditioned avoidance responses (CARs) without markedly affecting escape behavior in animals, indicative that they have antipsychotic-like effects. The serotonin receptor antagonist metergoline reversed the suppressio ...
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PFPP
''para''-Fluorophenylpiperazine (pFPP, 4-FPP, 4-Fluorophenylpiperazine; Fluoperazine, Flipiperazine) is a piperazine derivative with mildly psychedelic and euphoriant effects. It has been sold as an ingredient in legal recreational drugs known as "Party pills", initially in New Zealand and subsequently in other countries around the world. pFPP has been found ''in vitro'' to act mainly as a 5-HT1A receptor agonist, with some additional affinity for the 5-HT2A and 5-HT2C receptors. It has also been shown to inhibit the reuptake of serotonin and norepinephrine, and to possibly induce their release. pFPP was originally discovered as a metabolite of the hypnotic 5-HT2A and α1-adrenergic receptor antagonist niaprazine in 1982, but was rediscovered in 2003 as a potential recreational drug, and sold as an ingredient in "Party pills" in New Zealand, under brand names such as "The Big Grin", "Mashed", and "Extreme Beans". Subsequently it has continued to be used as an ingredient i ...
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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 recreational drug similarly to other piperazines like mCPP. Scientific research has demonstrated pCPP to have serotonergic effects, likely acting as a non- selective serotonin receptor agonist and/or releasing agent. A known use has been in the synthesis of L-745,870. See also * Substituted piperazine Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research. List of substituted piperazines Benzylpiperazines File:Benzylpiperazine.svg, 1- ... References {{DEFAULTSORT:Chlorophenylpiperazine, para- 4-Chlorophenyl compounds 1-Phenylpiperazines Psychedelic arylpiperazines Serotonin receptor agonists Serotonin releasing agent ...
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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 reuptake and induces the release of serotonin, dopamine, and norepinephrine to varying extents, and has been described as a serotonin antagonist and reuptake inhibitor (SARI). Usages Controlled clinical trials of mepiprazole in patients with irritable bowel syndrome (IBS) were also carried out and suggested some benefits of the drug in relieving symptoms of IBS in some patients. Similarly to other phenylpiperazines like trazodone, nefazodone, and etoperidone, mepiprazole produces ''m''CPP as an active metabolite An active metabolite, or pharmacologically active metabolite is a biologically active metabolite of a xenobiotic substance, such as a drug or environmental chemical. Active metabolites may produce therapeutic effects, as ...
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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 structure and is a serotonin antagonist and reuptake inhibitor (SARI) similarly to them. Medical uses Etoperidone was used or was intended for use as an antidepressant in the treatment of depression. Etoperidone might be useful as a hallucinogen antidote or "trip killer" in blocking the effects of serotonergic psychedelics like psilocybin and lysergic acid diethylamide (LSD). Pharmacology Pharmacodynamics Etoperidone is as an antagonist of several receptors in the following order of potency: 5-HT2A receptor (36 nM) > α1-adrenergic receptor (38 nM) > 5-HT1A receptor (85 nM) (may be a partial agonist) > α2-adrenergic receptor (570 nM); it has only very weak or negligible affinity for blocking the following receptors: D2 recepto ...
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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 2004 (due to liver toxicity), but was, as of December 2021, still available in the United States. The medication is taken by mouth. Side effects of nefazodone include dry mouth, sleepiness, nausea, dizziness, blurred vision, weakness, lightheadedness, confusion, and postural low blood pressure, among others. Rarely, nefazodone can cause serious liver damage, with an incidence of death or liver transplantation of about 1 in every 250,000 to 300,000 patient years. Nefazodone is a phenylpiperazine compound and is related to trazodone. It has been described as a serotonin antagonist and reuptake inhibitor (SARI) due to its combined actions as a potent antagonist of the serotonin 5-HT2A and 5-HT2C receptors and weak serotonin–norep ...
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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 orally. Common side effects include dry mouth, feeling faint, vomiting, and headache. More serious side effects may include suicide, mania, irregular heart rate, and pathologically prolonged erections. It is unclear if use during pregnancy or breastfeeding is safe. Trazodone also has sedating effects. Trazodone was approved for medical use in the United States in 1981. It is available as a generic medication. In 2022, it was the eighteenth most commonly prescribed medication in the United States, with more than 27million prescriptions. Medical uses Depression The primary use of trazodone is the treatment of unipolar major depression with or without anxiety. Data from open and double-blind trials suggest that the antidepressant eff ...
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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 phenylethyl group attached to the nitrogen atom at its 4-position. It was first described in 1994 in a patent disclosing a series of piperazine compounds as sigma receptor ligands. Later, it was discovered to be a highly potent dopamine reuptake inhibitor. Pharmacology 3C-PEP is one of the most potent dopamine transporter (DAT) ligands reported to date. It is highly selective for the dopamine transporter (dissociation constant K = 0.04 nM) with relatively low affinity for the closely related norepinephrine transporter (NET, K = 1107 nM ) and the serotonin transporter (SERT, K = 802 nM). In addition, the compound has lower (or no) affinity for the PCP/NMDA receptor (K > 10000 nM), D2-like receptors (K = 327 nM), ...
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1-(3-(Trifluoromethyl)phenyl)piperazine
3-Trifluoromethylphenylpiperazine (TFMPP) is a recreational drug of the phenylpiperazine chemical class and is a substituted piperazine. Usually in combination with benzylpiperazine (BZP) and other analogues, it is sold as an alternative to the illicit drug MDMA ("Ecstasy"). Use and effects TFMPP is rarely used by itself. In fact, TFMPP reduces locomotor activity and produces aversive effects in animals rather than self-administration, which may explain the decision of the DEA not to permanently make TFMPP a controlled substance. More commonly, TFMPP is co-administered with BZP, which acts as a norepinephrine and dopamine releasing agent. Due to the serotonin agonist effects and increase in serotonin, norepinephrine, and dopamine levels produced by the BZP/TFMPP combination, this mixture of drugs produces effects which crudely mimic those of MDMA. In a clinical study, TFMPP produced effects in humans including dysphoria, dextroamphetamine-like effects (i.e., stimulant-like ...
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1-(3-Chlorophenyl)piperazine
''meta''-Chlorophenylpiperazine (mCPP) is a psychoactive drug of the phenylpiperazine class. It was initially developed in the late-1970s and used in scientific research before being sold as a designer drug in the mid-2000s. It has been detected in pills touted as legal alternatives to illicit stimulants in New Zealand and pills sold as " ecstasy" in Europe and the United States. Despite its advertisement as a recreational substance, mCPP is actually generally considered to be an unpleasant experience and is not desired by drug users. It lacks any reinforcing effects, but has "psychostimulant, anxiety-provoking, and hallucinogenic effects." It is also known to produce dysphoric, depressive, and anxiogenic effects in rodents and humans, and can induce panic attacks in individuals susceptible to them. It also worsens obsessive–compulsive symptoms in people with the disorder. mCPP is known to induce headaches in humans and has been used for testing potential antimigraine me ...
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