N-Isopropyl Tadalafil

N-Isopropyl Tadalafil (Isopropylnortadalafil) Research Standard

N-Isopropyl Tadalafil (Isopropylnortadalafil) is a synthetic structural analog of tadalafil, classified within the tetrahydro-β-carboline (pyrazinopyridoindole-dione) class of phosphodiesterase type 5 (PDE5) inhibitors. Characterized by an N-isopropyl substitution on the terminal nitrogen of the piperazinedione ring, this compound serves as a specialized analytical reference standard. It is primarily utilized in forensic and pharmaceutical research to distinguish between closely related tadalafil derivatives, requiring orthogonal analytical methods for definitive structural elucidation.

Technical Specifications

Mechanism of Action & Structural Context

N-Isopropyl Tadalafil functions as a structural analog that engages the catalytic site of the PDE5 enzyme, similar to the parent compound, tadalafil.

• Structural Modification: The replacement of the N-methyl group (found in tadalafil) with an N-isopropyl group results in a mass shift of +28.05 (C2H4). This subtle modification is critical for researchers studying Structure-Activity Relationships (SAR) within the pyrazinopyridoindole-dione scaffold.

• Stereochemistry: The compound maintains the (6R,12aR) stereochemical configuration of the tadalafil scaffold. This stereospecificity is a primary determinant of binding affinity; therefore, analytical identification requires precise separation from other positional isomers.

• Enzyme Interaction: As a designer analog, it serves as a ligand to probe the steric and electronic constraints of the PDE5 catalytic pocket, allowing researchers to compare how branched alkyl chain substituents alter binding kinetics relative to linear counterparts.

Research Applications

Due to its positional and isobaric proximity to other tadalafil derivatives (e.g., nortadalafil, hydroxyethylnortadalafil), this compound is a critical reagent for high-fidelity analytical research.

Primary fields of in vitro laboratory investigation include:

• Orthogonal Method Development: Utilizing LC-HRMS (Liquid Chromatography-High Resolution Mass Spectrometry) and NMR (Nuclear Magnetic Resonance) to establish definitive structural fingerprints that separate N-isopropyl variants from other tadalafil homologs.

• Forensic & Pharmaceutical Analysis: Acting as an analytical reference material for the detection of designer PDE5-inhibitor analogs in complex samples.

• SAR Analysis: Investigating how the N-isopropyl substituent modulates enzyme-binding energy compared to standard tadalafil.

• Impurity Profiling: Providing a benchmark for the identification of potential synthetic by-products in PDE5-inhibitor chemical synthesis.

Storage & Handling Guidelines

To maintain the chemical stability and experimental reliability of the reference material:

• Storage Environment: Store as a lyophilized or solid powder in a sealed container.

• Environmental Control: Protect strictly from light and moisture.

• Vial Integrity: Keep the container tightly sealed to prevent atmospheric exposure.

• Verification: Always confirm lot-specific storage and reconstitution guidance provided on the accompanying Certificate of Analysis (COA) before use.

References

• Veldman K, et al. (2013) Identification and characterization of unapproved tadalafil analogs in dietary supplements. Journal of Pharmaceutical and Biomedical Analysis. 80:12–19.

• Venhuis BJ, et al. (2011) Designer drugs in herbal supplements: the identification of N-isopropyl tadalafil. Journal of Pharmaceutical and Biomedical Analysis. 55(4):1128–1132.

• FDA Laboratory Information Bulletin. (2012) Detection and Structural Elucidation of Tadalafil Analogs by LC-HRMS.

Research Use Disclaimer

Research Use Only Disclaimer: This product is developed and distributed strictly as a Research Use Only (RUO) laboratory reference chemical intended exclusively for non-clinical analytical and scientific investigation. It is not an FDA-approved drug, medical treatment, dietary supplement, or food ingredient, and is strictly prohibited for human or animal consumption. Kimera Chems supplies this high-purity research material solely to qualified institutions and professional investigators for authorized laboratory research.