CAS 521-40-4

(-)-Narcotoline

Description:

(-)-Narcotoline, with the CAS number 521-40-4, is an alkaloid derived from the opium poppy, Papaver somniferum. It is classified as a benzylisoquinoline alkaloid and is known for its structural complexity, featuring a fused ring system that includes a phenolic hydroxyl group. This compound exhibits a chiral center, resulting in its designation as (-)-narcotoline, indicating its specific stereochemistry. (-)-Narcotoline has been studied for its potential pharmacological effects, including analgesic and antinociceptive properties, although its exact mechanisms of action are not fully understood. It is important to note that, like many opiate derivatives, (-)-narcotoline may have implications for addiction and dependence. In terms of solubility, it is typically soluble in organic solvents but may have limited solubility in water. As with all alkaloids, safety and handling precautions are essential due to potential toxicity and regulatory considerations associated with its use in research and therapeutic applications.

Formula: C₂₁H₂₁NO₇

InChI: InChI=1S/C21H21NO7/c1-22-7-6-10-8-13-20(28-9-27-13)17(23)14(10)16(22)18-11-4-5-12(25-2)19(26-3)15(11)21(24)29-18/h4-5,8,16,18,23H,6-7,9H2,1-3H3/t16-,18+/m1/s1

InChI key: InChIKey=LMGZCSKYOKDBES-AEFFLSMTSA-N

SMILES: CN1[C@@]([C@@]2(C=3C(C(=O)O2)=C(OC)C(OC)=CC3)[H])(C4=C(C=C5C(=C4O)OCO5)CC1)[H]

Synonyms:

• (3S)-3-[(5R)-4-hydroxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-dimethoxy-2-benzofuran-1(3H)-one
• (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [S-(R*,S*)]-
• 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (3S)-
• 1,3-Dioxolo[4,5-g]isoquinoline, 1(3H)-isobenzofuranone deriv.
• Desmethylnarcotine
• Narcotoline
• (S-(R*,R*))-6,7-Dimethoxy-3-(5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)phthalide

Noscapine Impurity 6 (Narcotoline)

CAS: 521-40-4

Formula: C₂₁H₂₁NO₇

Molecular weight: 399.40

Ref: 4Z-N-061007

Desmethylnarcotine

CAS: 521-40-4

Applications Desmethylnarcotine is an impurity of Narcotoline an opiate alkaloid and a structure analogue of Nascapine (N882000), an antitussive agent. Noscapine (N882000) metabolite.
References Dhalstroem, B., et al.: Eur. J. Clin. Pharmacol., 22, 535 (1982), Al-Yahya, M.A., et al.: Anal. Profiles Drug Subs., 11, 407 (1982),

Formula: C₂₁H₂₁NO₇

Color and Shape: White Solid

Molecular weight: 399.39

Ref: TR-D292365

Desmethylnarcotine

CAS: 521-40-4

Desmethylnarcotine is an analog of narcotine that has been shown to be a potent inhibitor of kinases. It has been used as a medicinal compound in the development of anticancer drugs due to its ability to induce apoptosis in human cancer cells. Desmethylnarcotine acts as an inhibitor of protein kinases, which are involved in the regulation of cell growth and division. It has been found in urine samples and may have potential as a tumor marker for certain types of cancer. This compound is derived from Chinese medicinal plants and has shown promising results in preclinical studies as an anticancer agent.

Formula: C₂₁H₂₁NO₇

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 399.4 g/mol

Ref: 3D-AAA52140