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CAS 4747-98-2

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(-)-Tetrahydropapaverine

Description:
(-)-Tetrahydropapaverine is an organic compound classified as an alkaloid, specifically a derivative of papaverine. It is characterized by its complex bicyclic structure, which includes a tetrahydroisoquinoline moiety. This compound exhibits a chiral center, leading to its designation as the (-)-enantiomer, which is significant in pharmacological contexts due to the potential differences in biological activity between enantiomers. (-)-Tetrahydropapaverine is known for its vasodilatory properties and has been studied for its potential therapeutic applications, particularly in the treatment of conditions related to smooth muscle contraction. It is soluble in organic solvents and has limited solubility in water, which influences its bioavailability and formulation in medicinal applications. The compound's interactions with various receptors and enzymes contribute to its pharmacodynamic profile, making it a subject of interest in medicinal chemistry and drug development. As with many alkaloids, safety and toxicity profiles are essential considerations in its use and research.
Formula:C20H25NO4
InChI:InChI=1S/C20H25NO4/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-6,10-12,16,21H,7-9H2,1-4H3/t16-/m0/s1
InChI key:InChIKey=YXWQTVWJNHKSCC-INIZCTEOSA-N
SMILES:C([C@H]1C=2C(=CC(OC)=C(OC)C2)CCN1)C3=CC(OC)=C(OC)C=C3
Synonyms:
  • (-)-1,2,3,4-Tetrahydropapaverine
  • (-)-N-Norlaudanosine
  • (-)-Norlaudanosine
  • (-)-Tetrahydropapaverine
  • (1S)-1,2,3,4-Tetrahydro-6,7-dimethoxy-1-[(3,4-dimethoxyphenyl)methyl]Isoquinoline
  • (1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline
  • (S)-Norlaudanosine
  • <span class="text-smallcaps">L</span>-(-)-Tetrahydropapaverine
  • Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, (1S)-
  • Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, (S)-
  • See more synonyms
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