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Gelsemine information


Gelsemine
Gelsemine (gelsemin), an indole alkaloid
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 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
CAS Number
  • 509-15-9
PubChem CID
  • 279057
ChemSpider
  • 4536577
UNII
  • 5Y13A78Z72
Chemical and physical data
FormulaC20H22N2O2
Molar mass322.408 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN1C(C2CO3)[C@@H]4[C@]5(C(C=CC=C6)=C6NC5=O)[C@H]3C[C@H]2[C@]4(C=C)C1
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
  • Key:NFYYATWFXNPTRM-QJICHLCESA-N

Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas, and southeast Asia, and is a highly toxic compound that acts as a paralytic, exposure to which can result in death. It has generally potent activity as an agonist of the mammalian glycine receptor, the activation of which leads to an inhibitory postsynaptic potential in neurons following chloride ion influx, and systemically, to muscle relaxation of varying intensity and deleterious effect. Despite its danger and toxicity, recent pharmacological research has suggested that the biological activities of this compound may offer opportunities for developing treatments related to xenobiotic or diet-induced oxidative stress, and of anxiety and other conditions, with ongoing research including attempts to identify safer derivatives and analogs to make use of gelsemine's beneficial effects.[1][2]

  1. ^ Lin, Lin; Zheng, Jing; Zhu, Weiping; Jia, Ning (2015-03). "Nephroprotective Effect of Gelsemine Against Cisplatin-Induced Toxicity is Mediated Via Attenuation of Oxidative Stress". Cell Biochemistry and Biophysics. 71 (2): 535–541. doi:10.1007/s12013-014-0231-y. ISSN 1085-9195.
  2. ^ Liu, Ming; Huang, Hui-Hui; Yang, Jian; Su, Yan-Ping; Lin, Hong-Wei; Lin, Li-Qing; Liao, Wei-Jian; Yu, Chang-Xi (2013-02). "The active alkaloids of Gelsemium elegans Benth. are potent anxiolytics". Psychopharmacology. 225 (4): 839–851. doi:10.1007/s00213-012-2867-x. ISSN 0033-3158

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Gelsemine

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Gelsemine (C20H22N2O2) is an indole alkaloid isolated from flowering plants of the genus Gelsemium, a plant native to the subtropical and tropical Americas...

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Gelsemium sempervirens

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All parts of this plant contain the toxic strychnine-related alkaloids gelsemine and gelseminine and should not be consumed. The sap may cause skin irritation...

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Chloroform

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Clonazepam

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Gelsemium elegans

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China and other Asian countries. It contains toxic alkaloids such as gelsemine, gelsenicine, gelsevirine and koumine. Crumbled leaves of this plant,...

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Toluene

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Pentobarbital

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 1924

Tetrahydrocannabinol

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 5382

Taurine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Caffeine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Strychnine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Pregnenolone

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Diazepam

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Codeine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Methoxyflurane

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Colchicine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Propofol

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 5551

Barbiturate

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Flunitrazepam

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 3723

Pethidine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Diethyl ether

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Morphine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Ivermectin

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Nitrous oxide

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Sodium thiopental

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Pharmacology of ethanol

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

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Gelsemium

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present in a concentration of about 0.5%. These consist primarily of gelsemine (a highly toxic compound related to strychnine), with lesser amounts of...

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Furosemide

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 3650

Serine

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Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline...

Word Count : 2403

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