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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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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
Francisco León et al.
Natural product communications, 4(7), 907-910 (2009-09-08)
Mitragyna speciosa (Rubiaceae) has traditionally been used in the tropical regions of Asia, Africa and Indonesia as a substitute for opium. Indole alkaloids are the most common compounds that have been isolated. We investigated the constituents of the leaves of
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.
David M Pereira et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 17(8-9), 646-652 (2009-12-08)
The leaves of Catharanthus roseus constitute the only source of the well known indolomonoterpenic alkaloids vincristine and vinblastine. In this work we studied the biological potential of the roots, which are used in several countries as decocts or hot water
Roberts, M. F.
Alkaloids: biochemistry, ecology, and medicinal applications, 450-450 (1998)
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