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483-04-5

483-04-5 structure
483-04-5 structure
  • Name: Ajmalicine
  • Chemical Name: Raubasine
  • CAS Number: 483-04-5
  • Molecular Formula: C21H24N2O3
  • Molecular Weight: 352.427
  • Catalog: API Nervous system medication Brain metabolism regulating drug
  • Create Date: 2018-07-04 12:40:40
  • Modify Date: 2026-07-12 00:51:33
  • 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].
Name Raubasine
Synonyms Circolene
Raumalina
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
D-YOHIMBINE
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
(19α)-16,17-Didehydro-19-Methyl-oxayohiMban-16-cboxylic Acid Methyl Ester
fluoroajmalicine
Isoteril
delta-Yohimbine
Einecs 224-471-9
d-Yohimbine
RAUBASINE HYDROCHLORIDE
AJMALICINE
(19α)-16,17-Didehydro-19-methyl-oxayohimban-16-carboxylic acid methyl ester
Methyl (19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate
substanceii
gamma-Yohimbine
RAUBASIN
16,17-didehydro-19-methyloxayohimban-16-cboxylicacidmethylester
Tensyl
RAUBASINE
16,17-Didehydro-19-methyloxayohimban-16-cboxylic acid methyl ester
Tetrahydroserpentine
Rauvasan
Vincain
TETRAHYDROALSTONINE; AJMALICINE
4H-Indolo[2,3-a]pyrano[3,4-g]quinolizine, oxayohimban-16-cboxylic acid deriv
EINECS 207-589-5
AJMALICINE HCl(RG)
Pytetrahydroserpentine
Vincein
Ranitol
Raubasine //BP
oxayohimban-16-cboxylicacid,16,17-didehydro-19-methyl-,methylester,(19
yochimbine
Vinceine
Span
(4S,4,13bS,14aS)-Methyl 4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-cboxylate
Vincaine
AJMALICINE(-YOHIMBINE)
Alkaloid F
ALPHA-YOHIMBIN
Alkaloid C
Py-tetrahydroserpentine
alkaloidii
(19alpha)-16,17-Didehydro-19-methyloxayohimban-16-cboxylic acid methyl ester
Alkaloid II
Ajmalicine (base and/or unspecified salts)
Methyl-(19α)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylat
Vinceinen
Oxayohimban-16-cboxylic acid, 16,17-didehydro-19-methyl-, methylester, (19a)
Ajmalicin
Methyl 19-methyl-16,17-didehydrooxayohimban-16-cboxylate
Substance II
Vinceine (Raubasine)
δ-Yohimbine
AJMALICINE HCL
Raubasil
YOHIMBINE, C
Raubaserp
16,17-Didehydro-19alpha-methyloxayohimban-16-cboxylic acid methyl ester
Hydrospan
Oxayohimban-16-cboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19alpha)
7-[3-hydroxy-2-(3-hydroxy-1-octenyl)-5-oxocyclopentyl]
ajmalicine,monohydrochloride
19-iajmalicine
alkaloidf
alkaloidc
Sarpan
AJMALICIN HCL
Oxayohimban-16-cboxylic acid, 16,17-didehydro-19-methyl-, methyl ester, (19α)
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
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
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

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
Symbol GHS07
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)
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