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Tetrahydroalstonine

Names

[ CAS No. ]:
6474-90-4

[ Name ]:
Tetrahydroalstonine

[Synonym ]:
oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester
8-Methyl-5,6,7a,8,11a,12,12a,13-octahydro-7H-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic acid methyl ester
3S,15S,19S,20S-tetrahydroalstonine
ALSTONINE
Methyl (3ξ,19α,20α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
Tetrahydroalstonine
3,4,5,6-tetrahydro-alstonin
Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (3ξ,19α,20α)-
methyl 19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate

Biological Activity

[Description]:

Tetrahydroalstonine, a indole alkaloid isolated from the fruits of Rhazya stricta, is a selective alpha 2-adrenoceptor antagonist[1][2].

[Related Catalog]:

Research Areas >> Endocrinology
Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor
Research Areas >> Neurological Disease

[References]

[1]. Malik S, et al. Tetrahydroalstonine from Fruits of Rhazya stricta. Planta Med. 1984 Jun;50(3):283.

[2]. Roquebert J, et al. Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine. Eur J Pharmacol. 1984 Oct 30;106(1):203-5.https://www.ncbi.nlm.nih.gov/pubmed/6099269

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
524.0±50.0 °C at 760 mmHg

[ Melting Point ]:
227ºC

[ Molecular Formula ]:
C21H24N2O3

[ Molecular Weight ]:
352.427

[ Flash Point ]:
270.7±30.1 °C

[ Exact Mass ]:
352.178680

[ PSA ]:
54.56000

[ LogP ]:
2.88

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.656

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RP5776600
CHEMICAL NAME :
Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19-alpha,20-alpha)-
CAS REGISTRY NUMBER :
6474-90-4
BEILSTEIN REFERENCE NO. :
0097270
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C21-H24-N2-O3
MOLECULAR WEIGHT :
352.47

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #3969521

Synthetic Route

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Precursor & DownStream

Precursor

DownStream

Related Compounds