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5096-70-8

N-Methylcoclaurine is a naturally occurring chemical compound belonging to the benzylisoquinoline alkaloid family. It is predominantly found in plant species from the Corydalis and Papaver genera. N-Methylcoclaurine serves as a precursor in the biosynthesis of various alkaloids, including the potent analgesic morphine. Its pharmacological significance is further underscored by its sedative effects and ability to inhibit dopamine biosynthesis. However, the complex chemical structure of N-Methylcoclaurine presents challenges for synthetic production, thereby limiting its commercial availability.

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  • 7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-, (R)-

    Cas No: 5096-70-8

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  • 5096-70-8 Structure

  • Basic information

    1. Product Name: N-Methylcoclaurine
    2. Synonyms: (R)-(-)-N-Methylcoclaurine;(R)-N-Methylcoclaurine;D-Methylcoclaurine
    3. CAS NO:5096-70-8
    4. Molecular Formula: C18H21NO3
    5. Molecular Weight: 299.36424
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 5096-70-8.mol

  • Chemical Properties

    1. Melting Point: 184-185℃
    2. Boiling Point: 480.9°C at 760 mmHg
    3. Flash Point: 244.6°C
    4. Appearance: /
    5. Density: 1.214g/cm3
    6. Vapor Pressure: 7.14E-10mmHg at 25°C
    7. Refractive Index: 1.617
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 10.00±0.15(Predicted)
    11. CAS DataBase Reference: N-Methylcoclaurine(CAS DataBase Reference)
    12. NIST Chemistry Reference: N-Methylcoclaurine(5096-70-8)
    13. EPA Substance Registry System: N-Methylcoclaurine(5096-70-8)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5096-70-8(Hazardous Substances Data)

5096-70-8 Usage

Uses

Used in Pharmaceutical Industry:
N-Methylcoclaurine is used as a precursor molecule for the synthesis of various alkaloids, such as morphine, which is a highly potent analgesic. Its role in the production of these compounds is crucial for the development of pain-relief medications.
Used in Neuropharmacology Research:
N-Methylcoclaurine is used as a research compound for studying its sedative effects and its impact on dopamine biosynthesis. This application is valuable for understanding the compound's potential in the treatment of neurological disorders and conditions related to dopamine imbalances.
Used in Plant Biology Studies:
N-Methylcoclaurine is used as a marker compound in plant biology to investigate the biosynthetic pathways of alkaloids in plant species, particularly those from the Corydalis and Papaver genera. This research can provide insights into the plant's metabolic processes and potential applications in medicine and pharmacology.

Check Digit Verification of cas no

The CAS Registry Mumber 5096-70-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,0,9 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 5096-70:
(6*5)+(5*0)+(4*9)+(3*6)+(2*7)+(1*0)=98
98 % 10 = 8
So 5096-70-8 is a valid CAS Registry Number.
InChI:InChI=1/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

5096-70-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-N-methylcoclaurine

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5096-70-8 SDS

5096-70-8Downstream Products

5096-70-8Relevant articles and documents

Purification and characterization of coclaurine N-methyltransferase from cultured Coptis japonica cells

Choi, Kum-Boo,Morishige, Takashi,Sato, Fumihiko

, p. 649 - 655 (2007/10/03)

S-Adenosyl-L-methionine (SAM): coclaurine N-methyltransferase (CNMT), which catalyzes the transfer of a methyl group from S-adenosyl-L-methionine to the amino group of the tetrahydrobenzylisoquinoline alkaloid coclaurine, was purified 340-fold from Coptis japonica cells in 1% yield to give an almost homogeneous protein. The purified enzyme, which occurred as a homotetramer with a native Mr of 160 kDa (gel-filtration chromatography) and a subunit Mr of 45 kDa (SDS-polyacrylamide gel electrophoresis), had an optimum pH of 7.0 and a pI of 4.2. Whereas (R)-coclaurine was the best substrate for enzyme activity, Coptis CNMT had broad substrate specificity and no stereospecificity; CNMT methylated norlaudanosoline, 6,7-dimethoxyl-1,2,3,4-tetrahydroisoquinoline and 1-methyl-6,7-dihydroxy-1,2,3,4,-tetrahydroisoquinoline. The enzyme did not require any metal ion. p-Chloromercuribenzoate and iodoacetamide did not inhibit CNMT activity, but the addition of Co2+, Cu2+ or Mn2+ at 5 mM severely inhibited such activity by 75, 47 and 57%, respectively. The substrate-saturation kinetics of CNMT for norreticuline and SAM were of the typical Michaelis-Menten-type with respective Km values of 0.38 and 0.65 mM.

THE BIOSYNTHESIS OF THE ALKALOIDS OF CISSAMPELOS PAREIRA LINN

Bhakuni,Dewan S.,Jain,Sudha,Chaturvedi,Rekha

, p. 3975 - 3982 (2007/10/02)

Tracer experimets show that the bisbenzylisoqunoline alkaloid,(S,R)-hayatidin (10) is stereospecifically biosynthesized in young Cissampelos pareira Linn plants by intermolecular oxidativ coupling of (S)-(5)-and (R)-(3)-N-methylcoclaurines whereas (R,R)-isochondrodendrine (14) and (R,R)-bebeerine (12) are formed in the plants by oxidative dimerization of (R)-N-methyl-coclaurine (3).

THE BIOSYNTHESIS OF THE ALKALOIDS OF CROTON SPARSIFLORUS MORONG

Bhakuni, Dewan S.,Jain, Sudha

, p. 3175 - 3182 (2007/10/02)

Incorporation of tyrosine, dopa, dopamine, 4-hydroxyphenylpyruvic acid, (+/-)-, norcoclaurine-1-carboxylic acid, -norcoclaurine, -coclaurine, and -N-methylcoclaurine into N-methylcrotsparine, N-methylcrotsparinine and N-methylsparsiflorine in Croton sparsiflorus Morong has been studied.The evidence supports the direct oxidative coupling of (+)-, and (-)-N-methylcoclaurines to give N-methylcrotsparine and N-methylcrotsparinine, respectively.Tracer experiment show that N-methylcrotsparine undergoes dienone-phenol rearrangement to give N-methylsparsiflorine.A doublelabelling experiment with (+/-)-Nmethylcoclaurine demonstrated that the H atom at the asymmetric centre in the 1-benzylisoquinoline precursor is retained in the bioconversion.The intermediacy of norcoclaurine-1-carboxylic acid and specific incorporation of dehydro-N-methylcoclaurinium salt into the bases have been demonstrated.

Absolute Configuration and Biosynthesis of Tiliacorine and Tiliacorinine

Bhakuni, Dewan S.,Jain, Sudha

, p. 2598 - 2603 (2007/10/02)

The incorporation of (+/-)-coclaurine, (+/-)-norcoclaurine, (+/-)-N-methylcoclaurine, and didehydro-N-methylcoclaurinium iodide into tiliacorinine and tiliacorine in Tiliacora racemosa Colebr. has been studied, and specific utilization of the (+/-)-N-meth

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