Mesaconitine

Names

[ Name ]:
Mesaconitine

[Synonym ]:
13,14,15-pentol,1,6,16-trimethoxy-4-(methoxymethyl)-20-methyl-aconitane-8
Mesaaconitine
Aconitane-3,8,13,14,16-pentol, 1,6,15-trimethoxy-4-(methoxymethyl)-20-methyl-, 8-acetate 14-benzoate
N-Desethyl-N-Methylaconitine
MESACONITINE(SH)
Japaconitine B
Japaconitine A
8-Acetoxy-3,13,16-trihydroxy-1,6,15-trimethoxy-4-(methoxymethyl)-20-methylaconitan-14-yl benzoate
MESACONITINE (PRIMARY STANDARD)

Biological Activity

[Description]:

Mesaconitine is the main active component of genus aconitum plants.IC50 value:Target: in vitro: In HUVECs, 30 microM mesaconitine increased the [Ca(2+)](i) level in the presence of extracellular CaCl(2) and NaCl, and the response was inhibited by KBR7943. Mesaconitine increased intracellular Na(+) concentration level in HUVECs. The [Ca(2+)](i) response by mesaconitine was inhibited by 100 microM D-tubocurarine [1]. Mesaconitine at 30 microM inhibited 3 microM phenylephrine-induced contraction in the endothelium-intact, but not endothelium-denuded, aortic rings [2]. MA promoted the alpha-MT-induced decrease in NE levels in hippocampus, medulla oblongata plus pons and spinal cord [3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> TNF Receptor

Natural Products >> Alkaloid

Research Areas >> Others

[References]

[1]. Ogura J, et al. Mesaconitine-induced relaxation in rat aorta: role of Na+/Ca2+ exchangers in endothelial cells. Eur J Pharmacol. 2004 Jan 12;483(2-3):139-46.

[2]. Mitamura M, et al. Mesaconitine-induced relaxation in rat aorta: involvement of Ca2+ influx and nitric-oxide synthase in the endothelium. Eur J Pharmacol. 2002 Feb 2;436(3):217-25.

[3]. Murayama M, et al. Mechanism of analgesic action of mesaconitine. I. Relationship between analgesic effect and central monoamines or opiate receptors. Eur J Pharmacol. 1984 May 18;101(1-2):29-36.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
695.0±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₃H₄₅NO₁₁

[ Molecular Weight ]:
631.711

[ Flash Point ]:
374.1±31.5 °C

[ Exact Mass ]:
631.299255

[ PSA ]:
153.45000

[ LogP ]:
0.27

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.618

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AR5563000

CHEMICAL NAME :: Aconitane-3,8,13,14,15-pentol, 1,6,16-trimethoxy-4-(methoxymethyl)-20-methyl-, 8-acetate 14-benzoate, (1-alpha,3-alpha,6-alpha,14-alpha,15-alpha,16-beta)-

CAS REGISTRY NUMBER :: 2752-64-9

LAST UPDATED :: 199009

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C33-H45-N-O11

MOLECULAR WEIGHT :: 631.79

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 2,225,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 213 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YKKZAJ Yakugaku Zasshi. Journal of Pharmacy. (Nippon Yakugakkai, 2-12-15 Shibuya, Shibuya-ku, Tokyo 150, Japan) No.1- 1881- Volume(issue)/page/year: 97,359,1977

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 204 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 2,225,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJTOEX Japanese Journal of Toxicology. (Yakugyo Jihosha, Hokushin Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo, 101, Japan) V.1- 1988- Volume(issue)/page/year: 2,225,1989

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 80 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,873,1981

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,873,1981

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 40 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,873,1981

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H330

[ Precautionary Statements ]:
P260-P264-P284-P301 + P310-P310

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
24/25

[ RIDADR ]:
UN 1544

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Vasorelaxing effect of mesaconitine, an alkaloid from Aconitum japonicum, on rat small gastric artery: possible involvement of endothelium-derived hyperpolarizing factor Mitamura M, et al

Jpn. J. Pharmacol. 89(4) , 380-7, (2002)