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Merck
CN

41111

Ajmalicine

≥98.0% (HPLC)

Synonym(s):

δ-Yohimbine, Py-Tetrahydroserpentine, Raubasine

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About This Item

Empirical Formula (Hill Notation):
C21H24N2O3
CAS Number:
483-04-5
Molecular Weight:
352.43
MDL number:
MFCD00042748
UNSPSC Code:
12352200
EC Number:
207-589-5
NACRES:
NA.25
Beilstein/REAXYS Number:
97268

Key Documents

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SMILES string

N21[C@@H](C[C@H]5[C@@H]([C@@H](OC=C5C(=O)OC)C)C2)c3[nH]c4c(c3CC1)cccc4

InChI

1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1

InChI key

GRTOGORTSDXSFK-XJTZBENFSA-N

assay

≥98.0% (HPLC)

optical activity

[α]/D -65±3°, c = 1 in chloroform

mp

~258 °C (dec.)

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

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Application

Ajmalicine (δ-Yohimbine, Py-Tetrahydroserpentine, Raubasine) is an alkaloid used to study its effects as an antagonist of adrenergic and nicotinic receptors.

Biochem/physiol Actions

Metabolite in the indole alkaloid biosynthesis (serpentine production); found naturally in various plants such as Rauwolfia spp., Catharanthus roseus, and Mitragyna speciosa. It shows antimicrobial activity, and is used as an anti-hypertensive and sedative.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
BCBF4162
BCBF4162V

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Trends for diverse production strategies of plant medicinal alkaloids.
Liuqing Yang et al.
Natural product reports, 27(10), 1469-1479 (2010-08-24)
Catharanthus alkaloids and their enhanced production using elicitors: a review.
Gautam, S., et al.
International Journal of Pharmacy and Technology, 3, 713-724 (2011)
J Roquebert
Archives internationales de pharmacodynamie et de therapie, 282(2), 252-261 (1986-08-01)
The selectivity of raubasine and its two isomers tetrahydroalstonine (THA) and akuammigine (AKU) for alpha 1- and alpha 2-adrenoceptors has been investigated in pithed normotensive rats. alpha 1-Adrenoceptor blockade was measured by inhibition of the pressor response to (-)-phenylephrine. alpha
N M Rojas Hernández
Revista cubana de medicina tropical, 31(3), 199-204 (1979-09-01)
In pursuing the study of the antimicrobial properties of alkaloids prepared from Cuban plants the activity of 10 indol alkaloids and 4 semisynthetic variables obtained from three plants--Catharanthus roseus G. Don., Vallesia antillana Wood and Ervatamia coronaria Staph, of the
Roberts, M. F.
Alkaloids: biochemistry, ecology, and medicinal applications, 450-450 (1998)
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