Phenylpiperazine

Not to be confused with Substituted phenylpiperazine.

Phenylpiperazine

Names
Preferred IUPAC name

1-Phenylpiperazine

Identifiers

CAS Number

* 92-54-6 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL9434 Y

ChemSpider |

* 6829 Y

ECHA InfoCard | 100.001.969

PubChem CID

* 7096

UNII |

* J9225CBI7D Y

CompTox Dashboard (EPA)

* DTXSID8057855

InChI

* InChI=1S/C10H14N2/c1-2-4-10(5-3-1)12-8-6-11-7-9-12/h1-5,11H,6-9H2 Y

Key: YZTJYBJCZXZGCT-UHFFFAOYSA-N Y

SMILES

* c1cc(ccc1)N2CCNCC2

Properties

Chemical formula

| C10H14N2
Molar mass | 162.23 g/mol
Appearance  | clear colourless to yellow liquid
Density | 1.028g/cm3
Melting point | 18.8 °C (65.8 °F; 291.9 K)
Boiling point | 287.2 °C (549.0 °F; 560.3 K) at 760mmHg

Solubility in water

| insoluble
Hazards
Flash point | 138.3 °C (280.9 °F; 411.4 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

1-Phenylpiperazine (1-PP or PP) is a simple chemical compound and drug featuring a phenyl group bound to a piperazine ring.[1] The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class.[2]

It is a rigid analogue of amphetamine.[1][3][4] Similarly to amphetamine, 1-PP is a monoamine releasing agent, with EC50Tooltip half-maximal effective concentration values for monoamine release of 186 nM for norepinephrine, 880 nM for serotonin, and 2,530 nM for dopamine.[1] Based on the preceding values, it is about 4.7-fold less potent in releasing serotonin than norepinephrine and about 13.6-fold less potent in releasing dopamine than norepinephrine.[1] Hence, 1-PP is a modestly selective norepinephrine releasing agent (NRA), or could alternatively be thought of as an imbalanced serotonin–norepinephrine releasing agent (SNRA) or serotonin–norepinephrine–dopamine releasing agent (SNDRA).[1]

Other homologues and rigid analogues of amphetamine besides 1-PP include 2-aminotetralin (2-AT), 2-amino-1,2-dihydronaphthalene (2-ADN), 2-aminoindane (2-AI), 1-naphthylaminopropane (1-NAP), 2-naphthylaminopropane (2-NAP), 6-ABTooltip 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene, and 7-ABTooltip 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene.[3][4][5]

1-Phenylpiperazine shows toxicity at sufficiently high doses; its oral LD50 in rats is 210 mg/kg.[6]

Numerous derivatives of 1-PP, or substituted phenylpiperazines, exist.[7][1] Some examples include meta-chlorophenylpiperazine (mCPP), 3-trifluoromethylphenylpiperazine (TFMPP), and para-methoxyphenylpiperazine (pMeOPP).[7][1][8]

## See also

[edit]

* Substituted piperazine
* Serotonin antagonist and reuptake inhibitor
* Benzylpiperazine
* Diphenylpiperazine
* Diphenylmethylpiperazine
* Pyridinylpiperazine
* Pyrimidinylpiperazine

## References

[edit]

1. ^ a b c d e f g Severinsen K, Kraft JF, Koldsø H, Vinberg KA, Rothman RB, Partilla JS, Wiborg O, Blough B, Schiøtt B, Sinning S (September 2012). "Binding of the amphetamine-like 1-phenyl-piperazine to monoamine transporters". ACS Chem Neurosci. 3 (9): 693–705\. doi:10.1021/cn300040f. PMC 3447394. PMID 23019496.
2. ^ World Health Organization (WHO) (2006). "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances" (PDF). Archived from the original (PDF) on 2008-12-14. Retrieved 27 April 2010.
3. ^ a b Oberlender R, Nichols DE (March 1991). "Structural variation and (+)-amphetamine-like discriminative stimulus properties". Pharmacology, Biochemistry, and Behavior. 38 (3): 581–586\. doi:10.1016/0091-3057(91)90017-V. PMID 2068194. S2CID 19069907.
4. ^ a b Glennon RA, Young R, Hauck AE, McKenney JD (December 1984). "Structure-activity studies on amphetamine analogs using drug discrimination methodology". Pharmacol Biochem Behav. 21 (6): 895–901\. doi:10.1016/s0091-3057(84)80071-4. PMID 6522418.
5. ^ Hathaway BA, Nichols DE, Nichols MB, Yim GK (May 1982). "A new, potent, conformationally restricted analogue of amphetamine: 2-amino-1,2-dihydronaphthalene". Journal of Medicinal Chemistry. 25 (5): 535–538\. doi:10.1021/jm00347a011. PMID 6123601.
6. ^ "1-Phenylpiperazine". pubchem.ncbi.nlm.nih.gov.
7. ^ a b Elliott S (2011). "Current awareness of piperazines: pharmacology and toxicology". Drug Test Anal. 3 (7–8): 430–438\. doi:10.1002/dta.307. PMID 21744514.7–8&rft.pages=430-438&rft.date=2011&rft_id=info:doi/10.1002/dta.307&rft_id=info:pmid/21744514&rft.aulast=Elliott&rft.aufirst=S&rfr_id=info:sid/en.wikipedia.org:Phenylpiperazine" class="Z3988">
8. ^ Baumann MH, Clark RD, Budzynski AG, Partilla JS, Blough BE, Rothman RB (October 2004). "Effects of "Legal X" piperazine analogs on dopamine and serotonin release in rat brain". Ann N Y Acad Sci. 1025: 189–197\. doi:10.1196/annals.1316.024. PMID 15542717.

## External links

[edit]

* Media related to Phenylpiperazine at Wikimedia Commons

* v
* t
* e

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents|

* Morpholines: Fenbutrazate
* Fenmetramide
* Morazone
* Morforex
* Phendimetrazine
* Phenmetrazine
* Pseudophenmetrazine

* Oxazolines: 4-MAR
* Aminorex
* Clominorex
* Cyclazodone
* Fenozolone
* Fluminorex
* Pemoline
* Thozalinone

* Phenethylamines: 2-OH-PEA
* 4-CAB
* 4-FA
* 4-FMA
* 4-MA
* 4-MMA
* Alfetamine
* Amfecloral
* Amfepentorex
* Amfepramone
* Amphetamine (Dextroamphetamine
* Levoamphetamine)
* Amphetaminil
* β-Me-PEA
* BDB
* BOH
* Benzphetamine
* Buphedrone
* Butylone
* Cathine
* Cathinone
* Clobenzorex
* Clortermine
* D-Deprenyl
* DMA
* DMMA
* Dimethylamphetamine
* Ephedrine
* Ethcathinone
* EBDB
* Ethylone
* Etilamfetamine
* Famprofazone
* Fenethylline
* Fenproporex
* Flephedrone
* Fludorex
* Furfenorex
* Hordenine
* 4-Hydroxyamphetamine
* Iofetamine (123I)
* Lisdexamfetamine
* Lophophine
* Mefenorex
* Mephedrone
* Metamfepramone
* Methamphetamine
* Dextromethamphetamine
* Levomethamphetamine
* Methcathinone
* Methedrone
* MMDA
* MMDMA
* MBDB
* MDA (tenamfetamine)
* MDEA
* MDMA (midomafetamine)
* MDMPEA
* MDOH
* MDPEA
* Methylone
* Morforex
* Ortetamine
* pBA
* pCA
* pIA
* Pholedrine
* Phenethylamine
* Pholedrine
* Phenpromethamine
* Prenylamine
* Propylamphetamine
* Pseudoephedrine
* Tiflorex
* Tyramine
* Xylopropamine
* Zylofuramine

* Piperazines: 2C-B-BZP
* BZP
* MBZP
* MDBZP
* MeOPP
* oMPP

* Others: 2-ADN
* 2-AI
* 2-AT
* 4-BP
* 5-APDI
* 5-IAI
* Amineptine
* Clofenciclan
* Cyclopentamine
* Cypenamine
* Cyprodenate
* Feprosidnine
* Gilutensin
* Heptaminol
* Hexacyclonate
* Indanorex
* Isometheptene
* Methylhexanamine
* Naphthylaminopropane
* Octodrine
* Phthalimidopropiophenone
* Phenylbiguanide
* Propylhexedrine

NRAsTooltip Norepinephrine releasing agents|

* Morpholines: Fenbutrazate
* Fenmetramide
* Morazone
* Morforex
* Phendimetrazine
* Phenmetrazine
* Pseudophenmetrazine

* Oxazolines: 4-MAR
* Aminorex
* Clominorex
* Cyclazodone
* Fenozolone
* Fluminorex
* Pemoline
* Thozalinone

* Phenethylamines: 2-OH-PEA
* 4-CAB
* 4-FA
* 4-FMA
* 4-MA
* 4-MMA
* Alfetamine
* Amfecloral
* Amfepentorex
* Amfepramone
* Amphetamine
* Dextroamphetamine
* Levoamphetamine
* Amphetaminil
* β-Me-PEA
* BDB
* Benzphetamine
* BOH
* Buphedrone
* Butylone
* Cathine
* Cathinone
* Clobenzorex
* Clortermine
* Dimethylamphetamine
* DMA
* DMMA
* EBDB
* Ephedrine
* Ethcathinone
* Ethylone
* Etilamfetamine
* Famprofazone
* Fenethylline
* Fenproporex
* Flephedrone
* Fludorex
* Furfenorex
* Hordenine
* 4-Hydroxyamphetamine
* 5-APDI (IAP)
* Iofetamine (123I)
* Lisdexamfetamine
* Lophophine
* MBDB
* MDA (tenamfetamine)
* MDEA
* MDMA (midomafetamine)
* Metamfepramone
* MDMPEA
* MDOH
* MDPEA
* Mefenorex
* Mephedrone
* Mephentermine
* Methamphetamine
* Dextromethamphetamine
* Levomethamphetamine
* Methcathinone
* Methedrone
* Methylone
* Morforex
* Naphthylaminopropane
* Ortetamine
* pBA
* pCA
* Pentorex
* Phenethylamine
* Pholedrine
* Phenpromethamine
* Phentermine
* Phenylpropanolamine
* pIA
* Prenylamine
* Propylamphetamine
* Pseudoephedrine
* Selegiline (also D-Deprenyl)
* Tiflorex
* Tyramine
* Xylopropamine
* Zylofuramine

* Piperazines: 2C-B-BZP
* BZP
* MBZP
* mCPP
* MDBZP
* MeOPP
* oMPP
* pFPP

* Others: 2-ADN
* 2-AI
* 2-AT
* 2-BP
* 4-BP
* 5-IAI
* Clofenciclan
* Cyclopentamine
* Cypenamine
* Cyprodenate
* Feprosidnine
* Gilutensin
* Heptaminol
* Hexacyclonate
* Indanorex
* Isometheptene
* Methylhexanamine
* Octodrine
* Phthalimidopropiophenone
* Propylhexedrine
* Tuaminoheptane

SRAsTooltip Serotonin releasing agents|

* Aminoindanes: 5-IAI
* AMMI
* ETAI
* MDAI
* MDMAI
* MMAI
* TAI

* Aminotetralins: 6-CAT
* 8-OH-DPAT
* MDAT
* MDMAT

* Oxazolines: 4-Methylaminorex
* Aminorex
* Clominorex
* Fluminorex

* Phenethylamines: 2-Methyl-MDA
* 4-CAB
* 4-FA
* 4-FMA
* 4-HA
* 4-MTA
* 5-APDB
* 5-Methyl-MDA
* 6-APDB
* 6-Methyl-MDA
* AEMMA
* Amiflamine
* BDB
* BOH
* Brephedrone
* Butylone
* Chlorphentermine
* Cloforex
* Amfepramone
* Metamfepramone
* DCA
* Dexfenfluramine
* DFMDA
* DMA
* DMMA
* EBDB
* EDMA
* Ethylone
* Etolorex
* Fenfluramine
* Flephedrone
* Flucetorex
* IAP
* Iofetamine
* Levofenfluramine
* Lophophine
* MBDB
* MDA (tenamfetamine)
* MDEA
* MDHMA
* MDMA (midomafetamine)
* MDMPEA
* MDOH
* MDPEA
* Mephedrone
* Methedrone
* Methylone
* MMA
* MMDA
* MMDMA
* MMMA
* NAP
* Norfenfluramine
* 4-TFMA
* pBA
* pCA
* pIA
* PMA
* PMEA
* PMMA
* TAP

* Piperazines: 2C-B-BZP
* 3-MeOPP
* BZP
* DCPP
* MBZP
* mCPP
* MDBZP
* MeOPP
* Mepiprazole
* oMPP
* pCPP
* pFPP
* pTFMPP
* TFMPP

* Tryptamines: 4-Methyl-αET
* 4-Methyl-αMT
* 5-CT
* 5-MeO-αET
* 5-MeO-αMT
* 5-MT
* αET
* αMT
* DMT
* Tryptamine

* Others: Indeloxazine
* Viqualine

Others|

* DAT modulators: Agonist-like: SoRI-9804
* SoRI-20040; Antagonist-like: SoRI-20041

* Adrenergic release blockers: Bethanidine
* Bretylium
* Guanadrel
* Guanazodine
* Guanethidine
* Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

* v
* t
* e

Arylpiperazines

Phenylpiperazines|

* 1-Phenylpiperazine (1-PP; PP)
* 3,4-CFP
* 2C-B-PP
* Acaprazine
* Antrafenine
* Aripiprazole
* Batoprazine
* Bifeprunox
* BRL-15,572
* Ciprofloxacin
* Dapiprazole
* DCPP
* DMPP
* Diphenylpiperazine
* Dropropizine
* EGIS-7625
* EGIS-12,233
* Elopiprazole
* Eltoprazine
* Enpiprazole
* Ensaculin
* Etoperidone
* Flesinoxan
* Fluanisone
* Flibanserin
* Fluprazine
* Itraconazole
* Ketoconazole
* Levodropropizine
* Lorpiprazole
* mCPP
* Mefway
* MeOPP
* Mepiprazole
* Naftopidil
* Naluzotan
* Nefazodone
* Niaprazine
* Oxypertine
* Pardoprunox
* pCPP
* pFPP
* Posaconazole
* S-14,506
* S-14,671
* S-15,535
* SB-258,585
* SB-271,046
* SB-357,134
* SB-399,885
* Sonepiprazole
* TFMPP
* Tolpiprazole
* Trazodone
* Urapidil
* Vesnarinone
* Vilazodone
* Vortioxetine
* WAY-100,135
* WAY-100,635

Benzylpiperazines|

* 2C-B-BZP
* 3-Methylbenzylpiperazine
* Befuraline
* Bifeprunox
* Buclizine
* BZP
* Chlorbenzoxamine
* DBZP
* EGIS-7625
* Fipexide
* Imatinib
* MBZP
* MDBZP
* Meclozine
* Methoxypiperamide
* NSI-189
* Piberaline
* Piribedil
* RN-1747
* Sunifiram
* Trimetazidine
* Vesnarinone

Naphthylpiperazines|

* 1-Naphthylpiperazine (1-NP)
* 2-Naphthylpiperazine (2-NP)
* CSP-2503
* F-11,461
* S-14,506
* S-14671

Quinolinylpiperazines|

* FPPQ
* 6-Nitroquipazine
* Isoquipazine
* Quipazine

Diphenylalkylpiperazines|

* AD-1211
* Almitrine
* Amperozide
* BRL-15,572
* Buclizine
* BW373U86
* Cetirizine
* Chlorbenzoxamine
* Chlorcyclizine
* Cinnarizine
* Clocinizine
* Cyclizine
* DBL-583
* Diphenpipenol
* Diphenylmethylpiperazine
* Dotarizine
* DPI-221
* DPI-287
* DPI-3290
* GBR-12,783
* GBR-12,935
* GBR-13,069
* GBR-13,098
* GBR-13,119
* Hydroxyzine
* JJC8-088
* Lidoflazine
* Manidipine
* Meclozine
* MT-45
* Oxatomide
* SNC-80
* Vanoxerine

Pyrimidinylpiperazines|

* Buspirone
* Dasatinib
* Eptapirone
* Gepirone
* Ipsapirone
* Piribedil
* Pyrimidinylpiperazine
* Revospirone
* Tandospirone
* Tirilazad
* Trimazosin
* Umespirone
* Zalospirone

Pyridinylpiperazines|

* Atevirdine
* Azaperone
* Delavirdine
* Mirtazapine
* ORG-12962
* Pyridinylpiperazine

Benzo(iso)thiazolylpiperazines|

* Lurasidone
* Perospirone
* Revospirone
* Tiospirone
* Ziprasidone

Tricyclic-linked piperazines|

* Amoxapine
* Clopenthixol
* Clorotepine
* Clozapine
* Cyanothepin
* Doclothepin
* Docloxythepin
* Flupentixol
* Fluphenazine
* Isofloxythepin
* Loxapine
* Meperathiepin
* Metitepine
* Octomethothepin
* Olanzapine
* Opipramol
* Oxyclothepin
* Oxyprothepin
* Peradithiepin
* Perathiepin
* Perazine
* Perphenazine
* Pirenzepine
* Prochlorperazine
* Thiethylperazine
* Thiothixene
* Trifluoperazine
* Trifluthepin
* Zuclopenthixol

Others/uncategorized|

* AP-238
* Azimilide
* Bucinnazine
* Cinepazet
* Cinepazic acid
* Cinepazide
* CPD-1
* Cyclohexylpiperazine
* Hexocyclium
* Indinavir
* JNJ-7777120
* Lodenafil
* MK-212
* Mirodenafil
* PB-28
* Ranolazine
* SA-4503
* Sildenafil
* Tadalafil
* Vardenafil
* VUF-6002
* WY-46824
* Zipeprol

* v
* t
* e

Chemical classes of psychoactive drugs

Stimulants|

* Amphetamine-type/dopamine releasing agents: Alkylamines
* Cycloalkylaminopropanes
* Arylpiperazines
* Benzylpiperazines
* Phenylpiperazines
* Phenethylamines
* Aminorexes/phenyloxazolamines
* Amphetamines/α-methylphenethylamines
* Cathinones/β-ketoamphetamines
* β-Hydroxyamphetamines/cathinols
* Naphthylaminopropanes
* Phentermines
* Phenylisobutylamines/α-ethylphenethylamines
* α-Propylphenethylamines
* Phenylmorpholines/phenmetrazines
* Thiopropamines/thienylaminopropanes

* Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines
* Phenidates/benzylpiperidines
* Phenylethylpyrrolidines
* Pyrrolidinophenones
* Phenyltropanes/cocaine analogues

* Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues
* Phenylpiracetams

* Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines

* Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues

Depressants|

* GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues
* Barbiturates
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines
* Carbamates
* Ethers
* Neuroactive steroids
* Nonbenzodiazepines
* β-Carbolines
* Cyclopyrrolones
* Imidazopyridines
* Pyrazolopyrimidines
* Phenols
* Piperidinediones
* Quinazolinones

* GABAA receptor agonists: Isoxazoles

* GHB receptor agonists: 1,4-Butanediols

* α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids

* Opioids/μ-opioid receptor agonists: Benzimidazoles
* Nitazenes
* Fentanyl analogues/phenylpiperidines
* Mitragyna alkaloids
* Morphinans/phenanthrenes
* Opiates/opium alkaloids
* Utopioids

* Antihistamines/H1 receptor antagonists: Benzimidazoles
* Diarylmethanes
* Ethylenediamines
* Tricyclics
* Dibenzocycloheptenes

Hallucinogens|

* Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines
* Phenylpiperazines
* Quinolinylpiperazines
* Cyclized tryptamines
* Azepinoindoles
* Iboga alkaloids
* β-Carbolines
* Harmala alkaloids
* Ergolines
* Lysergamides
* Simplified/partial lysergamides
* Phenethylamines (methoxyphenethylamines)
* 2Cs
* 25-NB/NBOMes
* 2C-Os
* 2C-Ts
* HOT-x
* TWEETIOs
* Amphetamines/α-methylphenethylamines
* 3Cs
* Dimethoxyamphetamines/DMAs
* DOx
* Alephs
* Methylenedioxyamphetamines/MDxx
* Trimethoxyamphetamines/TMAs
* BOx
* FLYs/benzofurans
* Phenylisobutylamines/α-ethylphenethylamines
* 4Cs
* Scalines
* Tryptamines
* α-Alkyltryptamines
* α-Alkyl-β-ketotryptamines
* 4-Hydroxytryptamines
* 5-Hydroxytryptamines
* 5-Methoxytryptamines
* Miscellaneous

* Dissociatives/NMDA receptor antagonists: Adamantanes
* Arylcyclohexylamines
* Diarylethylamines
* Morphinans

* κ-Opioid receptor agonists: Benzomorphans
* Salvinorins

* GABAA receptor agonists: Isoxazoles

* Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes
* Tropanes

* Others: Cyclized tryptamines
* Azepinoindoles
* Iboga alkaloids
* (Phyto)cannabinoids

Entactogens|

* Serotonin releasing agents: Phenethylamines
* Aminoindanes
* Aminotetralins
* Amphetamines
* Benzofuranylaminopropanes
* Benzothiophenylaminopropanes
* Ethylenedioxyamphetamines
* Indanylaminopropanes
* Indolylaminopropanes
* Methylenedioxyamphetamine/MDxx
* Tetralinylaminopropanes
* Tryptamines
* α-Alkyltryptamines
* Miscellaneous

Psychiatric drugs|

* Anxiolytics: Azapirones
* Benzodiazepines
* Pyrrolobenzodiazepines
* Thienobenzodiazepines
* Thienodiazepines
* Thienotriazolodiazepines
* Triazolobenzodiazepines

* Antidepressants: Tricyclic antidepressants
* Dibenzazepines
* Dibenzocycloheptenes
* Dibenzothiepins
* Dibenzoxazepines
* Dibenzoxepins
* Tetracyclic antidepressants

* Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides
* Benzimidazoles
* Benzisothiazoles
* Benzisoxazoles
* Butyrophenones
* Diphenylbutylpiperidines
* Phenylpiperazines
* Tricyclics
* Dibenzazepines
* Dibenzodiazepines
* Dibenzothiazepines
* Dibenzothiepins
* Dibenzoxazepines
* Phenothiazines
* Thienobenzodiazepines

* Mood stabilizers/anticonvulsants: Gabapentinoids
* Tricyclics
* Dibenzazepines
* Valproates

Others|

* Nootropics: Racetams
* Phenylpiracetams

* Miscellaneous: Adamantanes
* Catecholamines
* Tetrahydroisoquinolines
* Yohimbans

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[EC50]: half-maximal effective concentration
*[6-AB]: 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene
*[7-AB]: 7-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DRAs]: Dopamine releasing agents
*[NRAs]: Norepinephrine releasing agents
*[SRAs]: Serotonin releasing agents