Phenylpiperazine

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]

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

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

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

References

1. 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. 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. 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. 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.
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

• Media related to Phenylpiperazine at Wikimedia Commons