Ajmalicine

Names

[ CAS No. ]:
483-04-5

[ Name ]:
Ajmalicine

[Synonym ]:
Circolene
EINECS 207-589-5
Pytetrahydroserpentine
Vincein
Ranitol
yochimbine
Vinceine
Methyl (4S,4aR,13bS,14aS)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate
Lamuran
Methyl-(4S,4aR,13bS,14aS)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]chinolizin-1-carboxylat
Methyl-(19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylat
fluoroajmalicine
Einecs 224-471-9
d-Yohimbine
δ-Yohimbine
RAUBASINE HYDROCHLORIDE
AJMALICINE HCL
(19α)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl ester
Methyl (19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
Raubasil
Raubasine
Ajmalicine
RAUBASIN
ajmalicine,monohydrochloride
Oxayohimban-16-carboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19α)-
Tensyl
Sarpan
AJMALICIN HCL
Tetrahydroserpentine
Rauvasan
Vincain

Biological Activity

[Description]:

Ajmalicine (Raubasine) is found in herbs of Catharanthus roseus, is an antihypertensive drug used in the treatment of high blood pressure, decreases peripheral resistance and blood pressure[1].Ajmalicine (Raubasine) is an adrenolytic drug which preferentially blocks alpha 1-adrenoceptor than alpha 2-adrenoceptor[2].Ajmalicine (Raubasine) is an reversible non-competitive nicotine receptor antagonist with an IC50 of 72.3 μM[3].Ajmalicine (Raubasine) acts preferentially at postsynaptic sites, competitively antagonizes the effect of noradrenaline on postsynaptic alpha-adrenoceptor with a pA2 value of 6.57, blocks the inhibitory effect of clonidine with an pA2 value of 6.2[4].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

Signaling Pathways >> Neuronal Signaling >> AChE

[References]

[1]. Wink, Michael; Roberts, M. W. (1998). Alkaloids: biochemistry, ecology, and medicinal applications. New York: Plenum Press. ISBN 0-306-45465-3.

[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.

[3]. Pereira DM, et al. Pharmacological effects of Catharanthus roseus root alkaloids in acetylcholinesterase inhibition and cholinergic neurotransmission. Phytomedicine. 2010 Jul;17(8-9):646-52.

[4]. • Demichel P, et al. Effects of raubasine stereoisomers on pre- and postsynaptic alpha-adrenoceptors in the rat vas deferens. Br J Pharmacol. 1984 Oct;83(2):505-10

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

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

[ Melting Point ]:
258°C (rough estimate)

[ 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

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AX7875000

CHEMICAL NAME :: Ajmalicine

CAS REGISTRY NUMBER :: 483-04-5

BEILSTEIN REFERENCE NO. :: 0097268

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C21-H24-N2-O3

MOLECULAR WEIGHT :: 352.47

WISWESSER LINE NOTATION :: T F6 D5 C666 EM ON SO TU&&TTTJ R1 UVO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 12500 ug/kg

TOXIC EFFECTS :: Behavioral - general anesthetic Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: CHETBF Chest. (American College of Chest Physicians, 911 Busse Hwy, Park Ridge, IL 60068) V.57- 1970- Volume(issue)/page/year: 76,97,1979

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 233,72,1958

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 200 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 24 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 165 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AEPPAE Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. (Berlin, Ger.) V.110-253, 1925-66. For publisher information, see NSAPCC. Volume(issue)/page/year: 233,72,1958

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 500 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 20 mg/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,117,1972

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 20 mg/kg

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

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 23,600,1973

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R25

[ Safety Phrases ]:
22-45

[ RIDADR ]:
UN 1544

[ RTECS ]:
AX7875000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Precursor & DownStream

Precursor

DownStream

Articles

Determination of terpenoid indole alkaloids in hairy roots of Rhazya stricta (Apocynaceae) by GC-MS.

Phytochem. Anal. 26 , 331-8, (2015)

Rhazya stricta Decne. (Apocynaceae) is a medicinal plant rich in terpenoid indole alkaloids (TIAs), some of which possess important pharmacological properties. The study material including transgenic ...

Synergistic and cytotoxic action of indole alkaloids produced from elicited cell cultures of Catharanthus roseus.

Pharm. Biol. 51(3) , 304-10, (2013)

Catharanthus roseus (L.) G. Don (Apocynaceae) is a medicinal plant that produces more than 130 alkaloids, with special attention given to the production of the anti-hypertensive monomeric indole alkal...

A differential response to chemical elicitors in Catharanthus roseus in vitro cultures.

Biotechnol. Lett. 31(4) , 591-5, (2009)

The effects of methyl jasmonate, salicylic acid and ethylene on alkaloid accumulation in in vitro cell suspension, hairy roots and rootless shoot cultures of Catharanthus roseus were analyzed. Ajmalic...