Amino Tadalafil

Synonyme: (6R,12aR)-2-Amino-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione; Amino Tadalafil; 385769-84-6; Pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione, 2-amino-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-, (6R,12aR)-

Amino Tadalafil is a synthetic analog of tadalafil, featuring a free amino group at the 2-position of the piperazine-2,6-dione ring. This modification introduces a site for further functionalization, making it a versatile intermediate in medicinal chemistry. The compound retains the characteristic tetracyclic scaffold of tadalafil, which is known for its high selectivity toward phosphodiesterase type 5 (PDE5).

As a research chemical, Amino Tadalafil is primarily used as a reference standard and synthetic intermediate. Its CAS number 385769-84-6 ensures precise identification in analytical and preparative workflows. The presence of the amino group allows for conjugation with various probes or affinity tags, facilitating studies on PDE5 binding and selectivity.

While not intended for therapeutic use, Amino Tadalafil serves as a critical tool for investigating the structure-activity relationships of PDE5 inhibitors. Its purity and consistency make it suitable for method development in HPLC and LC-MS applications, as well as for the synthesis of novel derivatives with potential pharmacological activity.

Chemical Structure & Properties

Amino Tadalafil shares the β-carboline-fused diketopiperazine core of tadalafil, with the addition of an amino substituent. This structural feature enhances its polarity and provides a handle for chemical modification. The compound is a white to off-white crystalline powder, stable under recommended storage conditions. It exhibits good solubility in organic solvents such as DMSO and methanol, but limited aqueous solubility.

Mechanism of Action

• PDE5 inhibition: The tetracyclic core binds to the catalytic domain of PDE5, though the amino group may alter affinity and selectivity compared to tadalafil.
• Research applications: Used to probe the binding mode of PDE5 inhibitors and to design fluorescent or affinity probes.
• Intermediate for derivatization: The amino group enables conjugation with carboxylic acids, activated esters, or isothiocyanates for targeted delivery or imaging.
• Selectivity studies: Helps elucidate the role of the 2-position in PDE isoenzyme selectivity.

Quality Specifications

Supply & Documentation

• Capacity: 10 kg per month
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS available upon request
• Verpackung: 25 kg fiber drum with double polyethylene liner, or customized packaging for small quantities

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com