gelsemine

gelsemin

CAS: 509-15-9 C20 H22 N2 O2 MW: 322.40774000

Identification

Namegelsemine
CAS Number509-15-9
EINECS208-095-2
FDA UNII5Y13A78Z72
Molecular FormulaC20 H22 N2 O2
Molecular Weight322.40774000
MDL NumberMFCD00082347
Beilstein5406576

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 178.00 °C. @ 760.00 mm Hg
Boiling Point 493.40 °C. @ 760.00 mm Hg (est)
Flash Point 486.00 °F. TCC ( 252.20 °C. ) (est)
logP (o/w) 3.080 (est)
Soluble in water, 625 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 49 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for gelsemine usage levels up tonot for fragrance use.
Recommendation for gelsemine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

gelsemium sempervirens

Synonyms

(3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5- ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one gelsemin PubMed: Nephroprotective Effect of Gelsemine Against Cisplatin-Induced Toxicity is Mediated Via Attenuation of Oxidative Stress. PubMed: Anti-hyperlipidemic and Anti-oxidative Effects of Gelsemine in High-Fat-Diet-Fed Rabbits. PubMed: High diluted molecules and gene expression. PubMed: In Silico Analysis to Compare the Effectiveness of Assorted Drugs Prescribed for Swine flu in Diverse Medicine Systems. PubMed: Extreme sensitivity of gene expression in human SH-SY5Y neurocytes to ultra-low doses of Gelsemium sempervirens. PubMed: Effects of Gelsemium sempervirens L. on pathway-focused gene expression profiling in neuronal cells. PubMed: Ultrasound/microwave-assisted extraction and comparative analysis of bioactive/toxic indole alkaloids in different medicinal parts of Gelsemium elegans Benth by ultra-high performance liquid chromatography with MS/MS. PubMed: Large-scale separation of alkaloids from Gelsemium elegans by pH-zone-refining counter-current chromatography with a new solvent system screening method. PubMed: Gelsemine, a principal alkaloid from Gelsemium sempervirens Ait., exhibits potent and specific antinociception in chronic pain by acting at spinal α3 glycine receptors. PubMed: Pharmacological effect of gelsemine on anxiety-like behavior in rat. PubMed: The active alkaloids of Gelsemium elegans Benth. are potent anxiolytics. PubMed: [Study on anti-proliferation activity and the mechanisms of alkaloid monomers from Gelsemium elegans on HepG2 cell in vitro]. PubMed: Biomimetic total synthesis of (+)-gelsemine. PubMed: Nectar alkaloids decrease pollination and female reproduction in a native plant. PubMed: Gelsemine and Gelsemium sempervirens L. Extracts in Animal Behavioral Test: Comments and Related Biases. PubMed: Preparative separation of alkaloids from Gelsemium elegans Benth. using pH-zone-refining counter-current chromatography. PubMed: Antitumor activity of two gelsemine metabolites in rat liver microsomes. PubMed: Simultaneous determination of six alkaloids in blood and urine using a hydrophilic interaction liquid chromatography method coupled with electrospray ionization tandem mass spectrometry. PubMed: Assays of homeopathic remedies in rodent behavioural and psychopathological models. PubMed: Consumption of a nectar alkaloid reduces pathogen load in bumble bees. PubMed: Comparative Analysis of Gelsemine and Gelsemium sempervirens Activity on Neurosteroid Allopregnanolone Formation in the Spinal Cord and Limbic System. PubMed: Confirmation of gelsemium poisoning by targeted analysis of toxic gelsemium alkaloids in urine. PubMed: Steroids, alkaloids, and coumarins from Gelsemium sempervirens. PubMed: A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy. PubMed: Nectar secondary compounds affect self-pollen transfer: implications for female and male reproduction. PubMed: Regulation of neurosteroid allopregnanolone biosynthesis in the rat spinal cord by glycine and the alkaloidal analogs strychnine and gelsemine. PubMed: Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine. PubMed: Pattern recognition in retrosynthetic analysis: snapshots in total synthesis. PubMed: Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine. PubMed: Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine. PubMed: Modeling the stereoselectivity of the Johnson-Claisen rearrangements in the Danishefsky synthesis of gelsemine. PubMed: A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine. PubMed: Gelsemine: a thought-provoking target for total synthesis. PubMed: Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine. PubMed: Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products. PubMed: Enantioselective Total Synthesis of (+)-Gelsemine: Determination of Its Absolute Configuration This work was supported in part by the Ministry of Education, Sports, and Culture, Japan. S.Y. thanks the JSPS for a predoctoral fellowship. PubMed: Total Synthesis of (+/-)-Gelsemine. PubMed: [Uses of hydroxamic acids and of N-alkoxyimidoyl halides in organic synthesis]. PubMed: A re-examination of the Na+-independent binding of [3H]beta-alanine to rat brain stem-spinal cord. PubMed: Cytotoxic steroids of Gelsemium sempervirens. PubMed: Studies on the NMR spectroscopic properties of gelsemine--revisions and refinements. PubMed: Gelsemine. PubMed: The Use of Duboisine, Gelsemine, Eserine etc., in Ophthalmic Practice.