GELSEMINE

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 Search

SMILES

[H][C@@]12C[C@H]3OC[C@@H]1[C@@]4([H])N(C)C[C@]2(C=C)[C@@]4([H])[C@@]35C(=O)NC6=CC=CC=C56

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23886522 | https://www.ncbi.nlm.nih.gov/pubmed/26388157

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glycine receptor subunit alpha-3 10 Target ID: P24524 Gene ID: NA Gene Symbol: Glra3 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23886522	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23886522 https://www.ncbi.nlm.nih.gov/pubmed/27128379	Primary	Preclinical	Unknown Approved Use Unknown
Hyperlipidemia 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25213292	Primary	Preclinical	Unknown Approved Use Unknown
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23850351	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Indole synthesis by radical cyclization of o-alkenylphenyl isocyanides and its application to the total synthesis of natural products.	2002	11933260
Explorations in organic chemistry leading to the total synthesis of (+/-)-gelsemine.	2002 Aug 21	12175241
Gelsemine: a thought-provoking target for total synthesis.	2003 Jan 3	19757588
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 Nov 5	14583006
Use of the intramolecular Heck reaction for forming congested quaternary carbon stereocenters. Stereocontrolled total synthesis of (+/-)-gelsemine.	2005 Dec 28	16366557
Aza-cope rearrangement-mannich cyclizations for the formation of complex tricyclic amines: stereocontrolled total synthesis of (+/-)-gelsemine.	2005 Dec 28	16366556
Double conjugate addition of a nitropropionate ester to a quinone monoketal: synthesis of an advanced intermediate to (+/-)-gelsemine.	2007 Aug 2	17628069
Pattern recognition in retrosynthetic analysis: snapshots in total synthesis.	2007 Jun 8	17539594
Regulation of neurosteroid allopregnanolone biosynthesis in the rat spinal cord by glycine and the alkaloidal analogs strychnine and gelsemine.	2008 Apr 22	18367344
Nectar secondary compounds affect self-pollen transfer: implications for female and male reproduction.	2008 Aug	18724731
Steroids, alkaloids, and coumarins from Gelsemium sempervirens.	2008 Dec	19016214
A concise approach to a gelsemine core structure using an oxygen to carbon bridge swapping strategy.	2008 Nov 6	18837555
Confirmation of gelsemium poisoning by targeted analysis of toxic gelsemium alkaloids in urine.	2009 Jan-Feb	19161670
Assays of homeopathic remedies in rodent behavioural and psychopathological models.	2009 Oct	19945676
Consumption of a nectar alkaloid reduces pathogen load in bumble bees.	2010 Jan	19711104
The genus Gelsemium: An update.	2010 Jul	22228960
Dose-effect study of Gelsemium sempervirens in high dilutions on anxiety-related responses in mice.	2010 Jul	20401745
Simultaneous determination of six alkaloids in blood and urine using a hydrophilic interaction liquid chromatography method coupled with electrospray ionization tandem mass spectrometry.	2010 Oct	20665006
Antitumor activity of two gelsemine metabolites in rat liver microsomes.	2010 Sep	20839118

Patents

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

GELSEMINE

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'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

NSC-21729

Code

English

Code System Code Type Description

ECHA (EC/EINECS)

208-095-2