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
| Property | Specification |
|---|---|
| Product Name | N-Isopropyl Tadalafil (Isopropylnortadalafil) |
| CAS Number | 171596-30-8 |
| Chemical Formula | C24H23N3O4 |
| Molecular Weight | ~417.46 g/mol |
| Chemical Class | Tetrahydro-β-carboline (PDE5 inhibitor analog) |
| Physical Appearance | Lyophilized / Solid powder |
| Assay Purity | Refer to the batch-specific Certificate of Analysis (COA) supplied for the lot received |
| Solution Base | PEG400, DMSO |
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.
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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.
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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.
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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:
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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.
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Forensic & Pharmaceutical Analysis: Acting as an analytical reference material for the detection of designer PDE5-inhibitor analogs in complex samples.
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SAR Analysis: Investigating how the N-isopropyl substituent modulates enzyme-binding energy compared to standard tadalafil.
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Impurity Profiling: Providing a benchmark for the identification of potential synthetic by-products in PDE5-inhibitor chemical synthesis.
Storage & Handling Guidelines
Store at controlled room temperature. Keep tightly closed. Liquid formats: do not refrigerate or freeze. Cold storage may cause the solution to cloud or precipitate. If this occurs, return to room temperature and mix until clear.
Storage guidance is a house recommendation. Analytical documentation is per-lot release testing.
References
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Veldman K, et al. (2013) Identification and characterization of unapproved tadalafil analogs in dietary supplements. Journal of Pharmaceutical and Biomedical Analysis. 80:12–19.
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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.
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FDA Laboratory Information Bulletin. (2012) Detection and Structural Elucidation of Tadalafil Analogs by LC-HRMS.
Related Research Compounds
Further reading: N-Isopropyl Tadalafil research overview
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 research material solely to qualified institutions and professional investigators for authorized laboratory research.
