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Gelsemine

Names

[ CAS No. ]:
509-15-9

[ Name ]:
Gelsemine

[Synonym ]:
GELSAMINE
8abeta,9s*,10s*))-8alph
GESEMINE
(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
Gelsemin
EINECS 208-095-2

Biological Activity

[Description]:

Gelsemine, an alkaloid from the Chinese herb Gelsemium elegans, is effective in mitigating chronic pain. Antinociceptive and hypnotic effects.

[Related Catalog]:

Signaling Pathways >> Others >> Others
Natural Products >> Alkaloid
Research Areas >> Neurological Disease

[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.


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Chemical & Physical Properties

[ 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

Toxicological Information

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

Safety Information

[ 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 & DownStream

Precursor

DownStream


Related Compounds