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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22N2O2
Molecular Weight 322.4009
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GELSEMINE

SMILES

CN1C[C@@]2(C=C)[C@@H]3C[C@H]4OC[C@@H]3[C@@H]1[C@@H]2[C@@]45C(=O)NC6=C5C=CC=C6

InChI

InChIKey=NFYYATWFXNPTRM-QJICHLCESA-N
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

HIDE SMILES / InChI
Molecular Formula C20H22N2O2
Molecular Weight 322.4009
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Gelsemine is the principal alkaloid in Gelsemium sempervirens Ait. A single intrathecal injection of gelsemine produced potent and specific antinociception in formalin-induced tonic pain, bone cancer-induced mechanical allodynia, and spinal nerve ligation-induced painful neuropathy. Gelsemine exhibits potent and specific antinociception in chronic pain by acting at spinal α3 glycine receptors. Gelsemine is an effective agent for treatment of both neuropathic pain and sleep disturbance in PSNL mice; anterior cingulate cortex might play a role in the hypnotic effects of gelsemine.

CNS Activity

Originator

Wormley, T.
2
Curator's Comment: Gelsemine, was first isolated by Wormley in 1870.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Glycine receptor subunit alpha-3
10
Target ID: P24524
Gene ID: NA
Gene Symbol: Glra3
Target Organism: Rattus norvegicus (Rat)
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Simultaneous determination of six alkaloids in blood and urine using a hydrophilic interaction liquid chromatography method coupled with electrospray ionization tandem mass spectrometry.
2010-10
Antitumor activity of two gelsemine metabolites in rat liver microsomes.
2010-09
The genus Gelsemium: An update.
2010-07
Dose-effect study of Gelsemium sempervirens in high dilutions on anxiety-related responses in mice.
2010-07
Consumption of a nectar alkaloid reduces pathogen load in bumble bees.
2010-01
Assays of homeopathic remedies in rodent behavioural and psychopathological models.
2009-10
Confirmation of gelsemium poisoning by targeted analysis of toxic gelsemium alkaloids in urine.
2009-01-24
Steroids, alkaloids, and coumarins from Gelsemium sempervirens.
2008-12
A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.
2008-11-06
Nectar secondary compounds affect self-pollen transfer: implications for female and male reproduction.
2008-08
Regulation of neurosteroid allopregnanolone biosynthesis in the rat spinal cord by glycine and the alkaloidal analogs strychnine and gelsemine.
2008-04-22
Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.
2007-08-02
Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.
2007-06-08
Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.
2005-12-28
Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.
2005-12-28
Modeling the stereoselectivity of the Johnson-Claisen rearrangements in the Danishefsky synthesis of gelsemine.
2005-09-02
A convenient one-pot procedure to afford bicyclic molecules by stereospecific iron carbonyl mediated [6 + 2] ene-type cyclization: a possible approach to gelsemine.
2003-11-05
Gelsemine: a thought-provoking target for total synthesis.
2003-01-03
Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.
2002-08-21
Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products.
2002
Patents

Patents

20150011767
2

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Oral route - Rabbits: were randomly divided into five groups and fed normal diet, hypercholesterolemic diet (1% cholesterol), or hypercholesterolemic diet (1% cholesterol) supplemented with gelsemine (1, 5, or 25 mg/kg). https://www.ncbi.nlm.nih.gov/pubmed/25213292
In PSNL mice, gelsemine (2 and 4 mg/kg) increased the mechanical threshold for 4 h and prolonged the thermal latencies for 3 h. Furthermore, gelsemine (4 mg/kg, administered at 6:30 AM) increased non-rapid eye movement (non-REM, NREM) sleep, decreased wakefulness, but did not affect REM sleep during the first 3 h in PSNL mice.
Route of Administration: Intraperitoneal
In Vitro Use Guide
Differential concentrations of gelsemine (1, 3, 10, 30, 100, 300, and 1000 uM) or glycine (3, 10, 30, 100, 300, and 1000 uM) were added to H3 -strychnine and the rat crude membrane. Both gelsemine and glycine concentration-dependently displaced H3 -strychnine binding by a maximum displacement of 100%. The IC50 values of gelsemine and glycine were 43.8 and 82.1 uM, and their Ki values were 21.9 and 41.0 uM, respectively.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:47:30 GMT 2025
Edited
by admin
on Mon Mar 31 21:47:30 GMT 2025
Record UNII
5Y13A78Z72
Record Status Validated (UNII)
Record Version
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Name Type Language
GELSEMINE
MI   WHO-DD  
Common Name English
NSC-21729
Preferred Name English
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)-
Systematic Name English
(3R-(3.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8A.BETA.,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
Systematic Name English
GELSEMINE [MI]
Common Name English
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.ALPHA.,4A.BETA.,5.ALPHA.,8.ALPHA.,8.ABETA.,9S*,10S*))-
Systematic Name English
Gelsemine [WHO-DD]
Common Name English
GELSEMIN [HSDB]
Common Name English
GELSEMINE, (+)-
Systematic Name English
Code System Code Type Description
DAILYMED
5Y13A78Z72
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-095-2
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
WIKIPEDIA
Gelsemine
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
FDA UNII
5Y13A78Z72
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
MERCK INDEX
m5688
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY Merck Index
NSC
21729
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
CAS
509-15-9
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
PUBCHEM
5390854
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
HSDB
3488
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID40878487
Created by admin on Mon Mar 31 21:47:30 GMT 2025 , Edited by admin on Mon Mar 31 21:47:30 GMT 2025
PRIMARY
NIH
NCATS
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