EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

gelsemine
gelsemin

Supplier Sponsors

CAS Number: 509-15-9Picture of molecule3D/inchi
Other(deleted CASRN):1413-63-4
ECHA EINECS - REACH Pre-Reg:208-095-2
FDA UNII: 5Y13A78Z72
Beilstein Number:5406576
MDL:MFCD00082347
XlogP3-AA:1.80 (est)
Molecular Weight:322.40774000
Formula:C20 H22 N2 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Gelsemine 98%
BOC Sciences
For experimental / research use only.
Gelsemine >98%
Odor: characteristic
Use: Gelsemine have marked antinociception in inflammatory, neuropathic and bone cancer pains without inducing antinociceptive tolerance. Antitumor
ExtraSynthese
For experimental / research use only.
Gelsemine (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Gelsemine
Sigma-Aldrich: Sigma
For experimental / research use only.
Gelsemine
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 49 mg/kg
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 349, 1957.

unreported-rat LDLo 60 ug/kg
"Dispensatory of the United States of America," 24th ed., Osol, A. and G.E. Farrar, Philadelphia, J.B. Lippincott Co., 1947Vol. 24, Pg. 497, 1947.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for gelsemine usage levels up to:
 not for fragrance use.
 
Recommendation for gelsemine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :56840800
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
Chemidplus:0000509159
RTECS:LX9100000 for cas# 509-15-9
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):56840800
Pubchem (sid):134977399
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 gelsemium sempervirens
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
from gelsemium sempervirens.
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