2-(Pyrrolidin-1-yl)phenylpentan-1-one
[CAS# 14530-33-7]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Pyrroles
• Name: 2-(Pyrrolidin-1-yl)phenylpentan-1-one
• Synonyms: 1-Phenyl-2-(1-pyrrolidinyl)-1-pentanone
• Molecular Formula: C₁₅H₂₁NO
• Molecular Weight: 231.33
• CAS Registry Number: 14530-33-7
• SMILES: CCCC(C(=O)C1=CC=CC=C1)N2CCCC2

Properties

• Density: 1.0±0.1 g/cm³ Calc.^*, 1.031 g/mL (Expl.)
• Melting point: 173 ºC (Expl.)
• Boiling point: 340.8±25.0 ºC 760 mmHg (Calc.)^*
• Flash point: 119.0±12.5 ºC (Calc.)^*
• Index of refraction: 1.538 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

2-(Pyrrolidin-1-yl)phenylpentan-1-one, also known by the abbreviation α-PVP (alpha-pyrrolidinovalerophenone), is a synthetic cathinone belonging to the class of substituted pyrrolidinophenones. Structurally, it is related to naturally occurring cathinone, the primary psychoactive alkaloid found in the khat plant (*Catha edulis*), but it features a pyrrolidine ring substitution on the nitrogen, which significantly alters its pharmacological properties. The compound is part of the broader family of synthetic stimulants that have appeared on the illicit drug market since the early 21st century.

The discovery of synthetic cathinones such as α--PVP is linked to medicinal chemistry research conducted during the mid-20th century, when numerous derivatives of cathinone and amphetamine were synthesized to investigate their potential as central nervous system stimulants or anorectic agents. While some pyrrolidinophenones were studied in the 1960s and 1970s, they did not progress to widespread pharmaceutical use. Decades later, α--PVP emerged in recreational contexts, first reported in Europe around 2011 and subsequently spreading to North America and other regions. Its appearance coincided with the rise of "bath salts" products containing various synthetic cathinones marketed as legal alternatives to controlled stimulants.

Pharmacologically, 2-(pyrrolidin-1-yl)phenylpentan-1-one functions primarily as a reuptake inhibitor of dopamine and norepinephrine, with limited activity at the serotonin transporter. This mechanism of action is similar to that of cocaine and other potent stimulants, leading to increased synaptic concentrations of monoamines and corresponding effects of euphoria, stimulation, alertness, and locomotor activation. Preclinical studies have shown that α--PVP has high potency at the dopamine transporter, contributing to its reinforcing properties and abuse potential.

The compound has no recognized medical use. Instead, it has been implicated in numerous cases of recreational abuse, often associated with severe adverse outcomes. Clinical and forensic reports describe toxic effects such as agitation, paranoia, hallucinations, tachycardia, hypertension, seizures, hyperthermia, and in severe cases, death. Its high potency and relatively long duration of action increase the risk of toxic overdose, particularly when used in combination with other psychoactive substances.

Applications of 2-(pyrrolidin-1-yl)phenylpentan-1-one are limited to forensic toxicology, pharmacology, and law enforcement monitoring. Analytical methods such as liquid chromatography–tandem mass spectrometry (LC-MS/MS), gas chromatography–mass spectrometry (GC-MS), and nuclear magnetic resonance (NMR) spectroscopy have been employed to detect and characterize the substance in seized materials and biological samples. Studies of its metabolism indicate that it undergoes hydroxylation, ketone reduction, and ring cleavage, producing metabolites that must be accounted for in toxicological analyses.

The compound has been classified as a controlled substance in many jurisdictions due to its lack of therapeutic value and high risk of abuse. In the United States, it is listed as a Schedule I substance under the Controlled Substances Act. Similar regulatory actions have been taken across Europe, Asia, and other regions to curb its availability and circulation.

The emergence of α--PVP as a recreational drug underscores the adaptability of clandestine laboratories in modifying existing stimulant scaffolds to produce new psychoactive substances. While structurally simple modifications to cathinone derivatives can yield powerful psychostimulants, their unregulated use poses significant public health risks. The story of 2-(pyrrolidin-1-yl)phenylpentan-1-one illustrates the broader challenges posed by designer stimulants and highlights the importance of ongoing surveillance, toxicological research, and regulatory efforts.

References

2023. Untargeted metabolomics analysis assisted by signal selection for comprehensively identifying metabolites of new psychoactive substances: 4-MeO-a-PVP as an example. Journal of Food and Drug Analysis, 31(1).
DOI: 10.38212/2224-6614.3447
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10208664

2022. Neuropsychopharmacology of Emerging Drugs of Abuse: meta- and para-Halogen-Ring-Substituted a-PVP (�flakka�) Derivatives. International Journal of Molecular Sciences, 23(4).
DOI: 10.3390/ijms23042226
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8876800

2006. 1-(4-Methylphenyl)-2-pyrrolidin-1-yl-pentan-1-one (Pyrovalerone) Analogues: A Promising Class of Monoamine Uptake Inhibitors. Journal of Medicinal Chemistry, 49(4).
DOI: 10.1021/jm050797a
URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2602954