Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H16N2O |
Molecular Weight | 204.2682 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C[C@@H]2C[C@H](C1)C3=CC=CC(=O)N3C2
InChI
InChIKey=CULUKMPMGVXCEI-QVDQXJPCSA-N
InChI=1S/C12H16N2O/c1-13-6-9-5-10(8-13)11-3-2-4-12(15)14(11)7-9/h2-4,9-10H,5-8H2,1H3/t9?,10-/m1/s1
Molecular Formula | C12H16N2O |
Molecular Weight | 204.2682 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15686946Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/4387392 | https://www.ncbi.nlm.nih.gov/pubmed/17703777 | https://www.ncbi.nlm.nih.gov/pubmed/19137500 | https://www.ncbi.nlm.nih.gov/pubmed/10543898
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686946
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/4387392 | https://www.ncbi.nlm.nih.gov/pubmed/17703777 | https://www.ncbi.nlm.nih.gov/pubmed/19137500 | https://www.ncbi.nlm.nih.gov/pubmed/10543898
Methylcytisine (Caulophylline) is a nicotinic alkaloid found in Caulophyllum thalictroides, also known as blue cohosh. Methylcytisine is a second potentially hazardous compound identified from blue cohosh. In cultured rat embryos, N-methylcytisine from blue cohosh caused major malformations. At a concentration of 20 ppm the effects included open anterior neural tube, poor or absent eye development, and twisted tail. Higher concentrations of Methylcytisine inhibited overall growth and morphogenesis, in addition to producing similar malformations. In a separate study, Methylcytisine was also found to stimulate the ganglion cells of the cardiac vagus in frogs, paralyze the ganglia of the cardiac vagus in dogs, and produce hyperglycemia in rabbits. Some of the actions of Methylcytisine are similar to nicotine. N-Methylcytisine in blue cohosh-containing dietary supplements has been measured at concentrations ranging from 5-850 ppm. No research has been conducted on the pharmacokinetics or pharmacodynamics of blue cohosh or its constituents; therefore, the clinical significance of the experiments discussed above remains unknown. However, women anticipating a pregnancy may want to avoid using blue cohosh-containing dietary supplements until the potential in vivo teratogenic effects of this botanical are understood.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19137500 |
|||
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686946 |
41.0 nM [EC50] | ||
Target ID: CHEMBL1907588 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15686946 |
37.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10543898
The in vitro embryo culture system was used for activity evaluation. On gestation day 9.5, rat embryos were dissected from the dams at developmental stages 11a-11c, and cultured as previously described. The medium consisted of 2.0 mL rat serum and 0.5 mL Waymouth’s MB 752/1 medium containing penicillin-streptomycin (250 units and 250 mkg/mL). Methylcytisine was dissolved in a solution of EtOH-DMSO (1:1) and then added to the culture medium (10 mkL) at the beginning of culture. After 45 h in culture, embryonic development was assessed.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 20:09:51 GMT 2023
by
admin
on
Fri Dec 15 20:09:51 GMT 2023
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Record UNII |
TT0MW69NCI
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Record Status |
Validated (UNII)
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Record Version |
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207-643-8
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TT0MW69NCI
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DTXSID80876866
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486-86-2
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m7391
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PARENT -> CONSTITUENT ALWAYS PRESENT |