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509-15-9

509-15-9 structure
509-15-9 structure
  • Name: Gelsemine
  • Chemical Name: Gelsemine
  • CAS Number: 509-15-9
  • Molecular Formula: C20H22N2O2
  • Molecular Weight: 322.401
  • Catalog: Natural product Alkaloid
  • Create Date: 2018-08-02 17:48:58
  • Modify Date: 2026-07-23 12:12:20
  • Gelsemine, an alkaloid from the Chinese herb Gelsemium elegans, is effective in mitigating chronic pain. Antinociceptive and hypnotic effects.
Name Gelsemine
Synonyms 3h)indol)-2’(1’,h)-one
(+)-Gelsemine
(3S,3aS,3'S,8S,8aS)-1-methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-iethane[1,1,2]triyl)oxino[4,5-b]pyrrole-4,3'-indolin]-2'-one
Gelsemin
GELSEMINE
Spiro[3,5,8-ethanylylidene-1H-pyrano[3,4-c]pyridine-10,3'-[3H]indole] , gelsemine deriv
ne,5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-,(3r-(3alpha,4abeta,5alpha
Gelsemine, 10 mM in DMSO
(3S,3aS,3'S,5R,8aS,9R)-1-Methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-iethane[1,1,2]triyl)oxino[4,5-b]pyrrole-4,3'-indolin]-2'-one
GELSAMINE
Gelsemine from Gelsemium elegans (Gdner & Chapm.) Benth
8abeta,9s*,10s*))-8alph
GESEMINE
Gelsemine in methanol
EINECS 208-095-2
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-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*)]-5-Etheny l-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro[3,5,8-ethanylylidene-1H-p yrano[3,4-c]pyridine-10,3'-[3H]indol]-2'(1'H)-one
(3S,3,3'S,5R,8S,8aS,9R)-1-methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-iethane[1,1,2]triyl)oxino[4,5-b]pyrrole-4,3'-indolin]-2'-one
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,4,5S,8S,8aS,9S)
octahydro-7-methylspiro(3,5,8-ethanylylidene-1h-pyrano(3,4-c)pyridine-10,3’-(
(2'S,3S,5'S,6'R,8'R,11'S)-4'-Methyl-2'-vinylspiro[indole-3,7'-[9]oxa[4]azatetracyclo[6.3.1.0.0]dodecan]-2(1H)-one
gelsemine free base
(3r-(3alpha,4abeta,5alpha,8alpha,8abeta,9s*,10s*))-5-ethenyl-3,4,4a,5,6,7,8,8a
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-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*)]
(3S,3,3'S,5R,8S,8aS,9R)-1-Methyl-3-vinyl-1,2,3,3a,5,7,8,8a-octahydrospiro[3,8,5-iethane[1,1,2]triyl)oxino[4,5-b]pyrrol-4,3'-indolin]-2'-one
Gelsemine-RM
spiro(3,5,8-ethanylylidene-1h-pyrano(3,4-c)pyridine-10,3’-(3h)indol)-2’(1’h)-o
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-(3alpha,4abeta,5alpha,8alpha,8abeta,9S,10S)]
Description Gelsemine, an alkaloid from the Chinese herb Gelsemium elegans, is effective in mitigating chronic pain. Antinociceptive and hypnotic effects.
Related Catalog
In Vivo Gelsemine is an effective agent for treatment of both neuropathic pain and sleep disturbance in partial sciatic nerve ligation (PSNL) mice. Gelsemine (4 mg/kg) exerts analgesic effects on PSNL-induced mechanical allodynia and thermal hyperalgesia. In PSNL mice, Gelsemine (2 and 4 mg/kg) increases the mechanical threshold for 4 h and prolonged the thermal latencies for 3 h. Furthermore, Gelsemine (4 mg/kg, administered at 6:30 AM) increases non-rapid eye movement (non-REM, NREM) sleep, decreases wakefulness, but does not affect rapid eye movement (REM) sleep during the first 3 h in PSNL mice[1]. Immunohistochemical study shows that PSNL increases c-Fos expression in the neurons of the anterior cingulate cortex, and Gelsemine (4 mg/kg) decreases c-Fos expression by 58%[1].
References

[1]. Wu YE, et al. Gelsemine alleviates both neuropathic pain and sleep disturbance in partial sciatic nerve ligation mice. Acta Pharmacol Sin. 2015 Nov;36(11):1308-17.
Density 1.3±0.1 g/cm3
Boiling Point 493.4±45.0 °C at 760 mmHg
Melting Point 181-183ºC
Molecular Formula C20H22N2O2
Molecular Weight 322.401
Flash Point 252.2±28.7 °C
Exact Mass 322.168121
PSA 41.57000
LogP 3.08
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.673

CHEMICAL IDENTIFICATION

RTECS NUMBER :
LX9100000
CHEMICAL NAME :
Gelsemine
CAS REGISTRY NUMBER :
509-15-9
BEILSTEIN REFERENCE NO. :
5406576
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C20-H22-N2-O2
MOLECULAR WEIGHT :
322.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DUSA** "Dispensatory of the United States of America," 24th ed., Osol, A. and G.E. Farrar, Philadelphia, J.B. Lippincott Co., 1947 Volume(issue)/page/year: 24,497,1947
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
49 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 7,349,1957
Hazard Codes T+
Risk Phrases 23/24/25-26/27/28
Safety Phrases 36/37/39-45-28
RIDADR UN 1544 6.1/PG 2
WGK Germany 3
RTECS LX9100000
Packaging Group I
Hazard Class 6.1(a)
Precursor  1

DownStream  0

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