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41111

Sigma-Aldrich

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
Beilstein:
97268
EC Number:
207-589-5
UNSPSC Code:
12352200
NACRES:
NA.25

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

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

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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

Signal Word

Danger

Hazard Statements

H300

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Catharanthus alkaloids and their enhanced production using elicitors: a review.
Gautam, S., et al.
International Journal of Pharmacy and Technology, 3, 713-724 (2011)
Trends for diverse production strategies of plant medicinal alkaloids.
Liuqing Yang et al.
Natural product reports, 27(10), 1469-1479 (2010-08-24)
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
P Demichel et al.
British journal of pharmacology, 83(2), 505-510 (1984-10-01)
The actions of raubasine, tetrahydroalstonine and akuammigine were studied on pre- and postsynaptic alpha-adrenoceptors of the rat vas deferens. These three drugs competitively antagonized the effect of noradrenaline on postsynaptic alpha-adrenoceptors, yielding pA2 values of 6.57, 4.56 and 4.68 respectively.
W G Kurz et al.
Planta medica, 42(1), 22-31 (1981-05-01)
A cell line of Catharanthus roseus (L.) G. Don coded PRL # 200, was characterized with respect to its biosynthetic capabilities for indolealkaloids, in particular catharanthine, in suspension cultures. Other alkaloids isolated are vallesiachotamine isomers, ajmalicine, hörhammericine, hörhammerinine, vindolinine, 19-epivindolinine
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