Amino Tadalafil Chemical Properties

Melting point:

280-282°C

Boiling point:

678.9±65.0 °C(Predicted)

Density 

1.60±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Store in freezer, under -20°C

solubility 

Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

16.70±0.40(Predicted)

color 

White to Off-White

InChI

InChI=1S/C21H18N4O4/c22-24-9-18(26)25-15(21(24)27)8-13-12-3-1-2-4-14(12)23-19(13)20(25)11-5-6-16-17(7-11)29-10-28-16/h1-7,15,20,23H,8-10,22H2/t15-,20-/m1/s1

InChIKey

VUKJGAVIWMPOOJ-FOIQADDNSA-N

SMILES

N1C2=C(C=CC=C2)C2C[C@]3([H])C(=O)N(N)CC(=O)N3[C@H](C3=CC=C4OCOC4=C3)C1=2

CAS DataBase Reference

385769-84-6

Safety Information

Safety Statements 

24/25

HS Code 

29339900

Amino Tadalafil Usage And Synthesis

Description

Amino tadalafil is an analog of tadalafil , a potent inhibitor of phosphodiesterase 5 with applications in several conditions, including erectile dysfunction, pulmonary arterial hypertension, and lower urinary tract dysfunction. Amino tadalafil has been detected as an illegal adulterant in a dietary supplement marketed for “tonic effect.”

Chemical Properties

White Solid

Uses

Amino Tadalafil is a drug analog of Tadalafil that used to treatment of male erectile dysfunction drugs.

Mechanism of action

Amino tadalafil is a potent inhibitor of phosphodiesterase 5 (PDE5).PDE5, an enzyme found primarily in the smooth muscle of the corpus cavernosum, selectively cleaves and degrades cGMP to 5′-GMP. PDE5 inhibitors are similar in structure to cGMP and they competitively bind to PDE5 and inhibit cGMP hydrolysis, thus enhancing the effects of NO, resulting in prolonging an erection.

in vitro

amino-tadalafil is a structural analogue of tadalafil, the active pharmaceutical ingredient in cialis, a prescription drug approved in the us for treatment of erectile dysfunction (ed). similarly, there have also been reports of herbal or dietary supplements being adulterated with designer ed analogues such as amino-tadalafil [1].

in vivo

in rats treated with both melatonin and tadalafil, the recoveries were more pronounced than in rats given either melatonin or tadalafil alone. the icp/mean arterial pressure value in vehicle-treated rats was significantly higher than in the control group, while in the tadalafil- and tadalafil + melatonin-treated groups have returned this value had returned to control levels. in addition, as an individual treatment, and especially when combined with tadalafil, melatonin prevented spinal cord injury (sci)-induced oxidative damage to cavernosal tissues and restored ed, most likely due to its anti-oxidant effects [2].

References

[1] hadwiger me, trehy ml, ye w, moore t, allgire j, westenberger b. identification of amino-tadalafil and rimonabant in electronic cigarette products using high pressure liquid chromatography with diode array and tandem mass spectrometric detection. j chromatogr a. 2010 nov 26;1217(48):7547-55.
[2] tavuk u hh, sener te, tinay i, akbal c, er ahin m, cevik o, cadirci s, reiter rj, sener g. melatonin and tadalafil treatment improves erectile dysfunction after spinal cord injury in rats. clin exp pharmacol physiol. 2014 apr;41(4):309-16.

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