CAS 509-15-9

(+)-Gelsemine

Description:

(+)-Gelsemine is an alkaloid derived from the plant Gelsemium sempervirens, commonly known as yellow jasmine. It is characterized by its complex bicyclic structure, which includes a fused indole and a piperidine ring. This compound is known for its potent neurotoxic properties, affecting the central nervous system and potentially leading to paralysis or respiratory failure in high doses. (+)-Gelsemine exhibits a range of biological activities, including analgesic and anti-inflammatory effects, making it of interest in pharmacological research. The substance is typically found as a white to pale yellow crystalline solid and is sparingly soluble in water but more soluble in organic solvents. Its stereochemistry is significant, as the (+) designation indicates the specific optical activity of the molecule. Due to its toxicity, handling (+)-Gelsemine requires caution, and it is primarily studied in controlled laboratory settings. Research continues to explore its potential therapeutic applications while also understanding the mechanisms underlying its toxic effects.

Formula: C₂₀H₂₂N₂O₂

InChI: InChI=1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13+,15+,16+,17-,19-,20-/m0/s1

InChI key: InChIKey=NFYYATWFXNPTRM-QJICHLCESA-N

SMILES: O=C1[C@@]2([C@@]3([C@]4(C=C)[C@@]5(C[C@]2(OC[C@@]5([C@]3(N(C)C4)[H])[H])[H])[H])[H])C=6C(N1)=CC=CC6

Synonyms:

• (3R,3′S,4aR,5S,8S,8aS,9S)-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
• (3S,3aR,4S)-3-ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1H,5H-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'H)-one
• (3S,3aS,4S,5R,8S,8aS)-3-ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1H,5H-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'H)-one
• (3S,3aS,4S,5R,8S,8aS,9R)-3-ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1H,5H-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'H)-one
• 3-ethenyl-1-methyl-2,3,3a,7,8,8a-hexahydro-1H,5H-spiro[3,8,5-(ethane[1,1,2]triyl)oxepino[4,5-b]pyrrole-4,3'-indol]-2'(1'H)-one
• Gelsemine
• NSC 21729
• Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3′-[3H]indol]-2′(1′H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R,3′S,4aR,5S,8S,8aS,9S)-
• [3R-(3α,4aβ,5α,8α,8aβ,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

Gelsemine

CAS: 509-15-9

Gelsemine analytical standard provided with chromatographic purity, to be used as reference material for qualitative determination.

Formula: C₂₀H₂₂N₂O₂

Purity: (HPLC) ≥95%

Color and Shape: Powder

Molecular weight: 322.41

Ref: 11-0619

Gelsemine

CAS: 509-15-9

Gelsemine

Purity: ≥98%

Molecular weight: 322.4g/mol

Ref: 54-BUP13233

Gelsemine

CAS: 509-15-9

Gelsemine is a highly toxic compound and may be a glycine receptor agonist. Gelsemine has antitumor, anti-hyperlipidemic,anti-oxidative activities,it also has marked antinociception in inflammatory, neuropathic and bone cancer pains without inducing antinociceptive tolerance.

Formula: C₂₀H₂₂N₂O₂

Purity: 95%~99%

Molecular weight: 322.408

Ref: BP-BP0629

Gelsemine

CAS: 509-15-9

Formula: C₂₀H₂₂N₂O₂

Molecular weight: 322.41

Ref: 4Z-G-190001

Gelsemine

CAS: 509-15-9

Gelsemine exhibits antitumor, antioxidative, anti-hyperlipidemic properties and strong antinociception without tolerance.

Formula: C₂₀H₂₂N₂O₂

Purity: 98.22% - 99.81%

Color and Shape: Crystals From Acetone White Powder

Molecular weight: 322.4

Ref: TM-T5S0662

Gelsemine

CAS: 509-15-9

Natural alkaloid

Formula: C₂₀H₂₂N₂O₂

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 322.41

Ref: 5G-80457

Gelsemine

Controlled Product

CAS: 509-15-9

Applications Gelsemine is the principle alkaloid of the yellow jasmine (Gelsemium). Gelsemine activates spinal α3 glycine receptors which produces antinociception and gelsemine contains anxiolytic properties.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Meyer, L., et. al.: Behav. Brain Res., 253, 90 (2013); Zhang, J., et. al.: Pain, 154, 2452 (2013)

Formula: C₂₀H₂₂N₂O₂

Color and Shape: Off-White

Molecular weight: 322.40

Ref: TR-G304560

Gelsemine

CAS: 509-15-9

Formula: C₂₀H₂₂N₂O₂

Molecular weight: 322.41

Ref: 7W-GY6878