CAS 5096-70-8

(-)-N-Methylcoclaurine

Description:

(-)-N-Methylcoclaurine, with the CAS number 5096-70-8, is a naturally occurring alkaloid belonging to the class of compounds known as benzylisoquinoline alkaloids. It is characterized by its structural features, which include a methoxy group and a methyl group attached to the nitrogen atom, contributing to its unique properties. This compound is typically found in various plant species, particularly in the family of Papaveraceae. (-)-N-Methylcoclaurine exhibits biological activity, including potential pharmacological effects, which have drawn interest in the fields of medicinal chemistry and pharmacognosy. Its stereochemistry is significant, as the (-) designation indicates its specific optical activity, which can influence its interaction with biological systems. The compound is often studied for its role in biosynthetic pathways leading to more complex alkaloids, such as morphine and codeine. Overall, (-)-N-Methylcoclaurine serves as an important subject of research due to its potential therapeutic applications and its role in plant metabolism.

Formula: C₁₈H₂₁NO₃

InChI: InChI=1S/C18H21NO3/c1-19-8-7-13-10-18(22-2)17(21)11-15(13)16(19)9-12-3-5-14(20)6-4-12/h3-6,10-11,16,20-21H,7-9H2,1-2H3/t16-/m1/s1

InChI key: InChIKey=BOKVLBSSPUTWLV-MRXNPFEDSA-N

SMILES: C([C@@H]1C=2C(=CC(OC)=C(O)C2)CCN1C)C3=CC=C(O)C=C3

Synonyms:

• (-)-N-Methylcoclaurine
• (1R)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol
• (R)-(-)-N-Methylcoclaurine
• (R)-1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol
• 1β<span class="text-smallcaps">H</span>-Coclaurine, 2-methyl-
• 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-2-methyl-, (R)-
• 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-, (1R)-
• <span class="text-smallcaps">D</span>-(-)-N-Methylcoclaurine
• <span class="text-smallcaps">D</span>-Methylcoclaurine
• l-N-Methylcoclaurine
• D-Methylcoclaurine

(-)-N-methylcoclaurine

CAS: 5096-70-8

N-Methylcoclaurine binds ĸ opioid receptor (Ki = 0.9 µM) and inhibits butyrylcholinesterase (IC50 = 15 µM).

Formula: C₁₈H₂₁NO₃

Purity: 98%

Color and Shape: Solid

Molecular weight: 299.36

Ref: TM-TN4613

N-Methylcoclaurine

CAS: 5096-70-8

Formula: C₁₈H₂₁NO₃

Purity: 95%~99%

Molecular weight: 299.37

Ref: BP-SBP03643

(R)-N-Methylcoclaurine

CAS: 5096-70-8

(R)-N-Methylcoclaurine is an isoquinoline alkaloid, a type of secondary metabolite, typically found in plants within the family Ranunculaceae and Papaveraceae. It is synthesized in these plants through the benzylisoquinoline alkaloid pathway, originating from the amino acid tyrosine. The compound functions as a biochemical precursor in the biosynthesis of more complex alkaloids.

Formula: C₁₈H₂₁NO₃

Purity: Min. 95%

Molecular weight: 299.4 g/mol

Ref: 3D-FAA09670