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(9R,10S,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-triene-14,18-diol

HCID 174236
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Basic information

CAS
4360-12-7
Standard SMILES
CC[C@H]1C2C[C@H]3[C@@H]4N(C)c5ccccc5C45C[C@@H](C2[C@H]5O)N3[C@@H]1O
InChIKey
CJDRUOGAGYHKKD-IWMNNKGHSA-N
Molecular formula
C20H26N2O2
Average molar mass
326.4 g/mol
Monoisotopic mass
326.19942808

Names & identifiers

Preferred name
(9R,10S,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-triene-14,18-diol
IUPAC
(9R,10S,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-triene-14,18-diol
English name
AJMALINE
Molecular formula
C20H26N2O2
Molecular weight
326.43

Names & synonyms

AKOS015965243EBC-615913AC-20176(9R,10S,13S,14R,16S,18R)-13-ethyl-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2(7),3,5-triene-14,18-diol5H-6,10:11,12a-Dimethanoindolo[3,2-b]quinolizine, ajmalan-17,21-diol deriv.RitmosAjmalinIgnazinTakycorAJMALINEAritminaRytmalin
Show more names
SiddiquiTajmalin

Database identifiers

CAS
4360-12-7
PubChem CID
174236

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
46.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
24
Formal charge
0
Complexity
570

Physicochemical properties

Melting point
189 °C · 189°C
alpha
18 · D18 +131° (c = 0.4 in chloroform); D20 +144° (c = 0.8 in chloroform)
Boiling point
464.47 °C · 464.47°C (rough estimate)
Density
1.1117 · 1.1117 (rough estimate)
refractive index
1.68 · 1.6800 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly)
form
Solid
pka
8.2 · pKa 8.2 (Uncertain)
color
White
optical activity
14420 · +14420 (CHCl3)
Water Solubility
489.7 mg/L · 489.7mg/L(30 ºC)
Merck
13 · 13,194
LogP
1.81 · 1.810
EWG's Food Scores
1 · 1
FDA UNII
1 PON08459R · 1PON08459R

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

rtecs
AX8050000
ridadr
1544
Toxicity
LD50 oral in rat: 360mg/kg
risk_code
25-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn
safety_code
13-45-36
hazard_class
6.1(b)
packing_group
III
Hazard statements
H302-H312-H332
Precautionary statements
P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312

Chemistry & industry

Applications · 4 items

DescriptionRauwolfia (Luo Fu Mu) is derived from the plants Rauvolfia verticillata (Lour.) Baill. and R. yunnanensis Tsiang, and the root is usually used as its medicinal part. R. verticillata (Lour.) Baill. var. hainanensis Tsiang and R. vomitoria Afzel. ex Spreng have been also used as traditional Chinese herb. Rauwolfia is one of the important traditional herbs in southern China. Its scope of treatment includes cold, fever, sore throat, headache, and dizziness caused by hypertension, abdominal pain and diarrhea, scabies, and so on. Rauwolfia is also used to treat insomniac dizziness, bruises, sprains, and venomous snake bites in folk. In the “Flora of China,” 135 species of Rauwolfia were recorded, mostly distributed in the tropics and subtropics, a few in the temperate regions. There are nine species, four varieties, and three cultivated species in China.

HistorySince 1930s, abundant studies have been focused on the Rauwolfia plants. So far, a total of 91 alkaloids were separated from Rauwolfia, and the identification of the chemical structures was obtained, including 2 non-indole alkaloids (thebaine and papaverine) and 89 indole alkaloids . In accordance with the basic framework, indole alkaloids can be divided into seven classes, such as the ajmaline class, the

UsesAn antiarrhythmic agent isolated from Rauwolfia serpentina.

UsesFor use as an antiarrhythmic agent.

Upstream & downstream products

Upstream raw materials

AmmoniaAcetic acid

Downstream products

(+)-Isoajmaline

Additional notes

DefinitionChEBI: A monoterpenoid indole alkaloid that consists of ajmalan substituted at positions 17 and 21 by hydroxy groups.

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
ATC code
1 BA05 · C01BA05
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H312-H332
Precautionary statements
264 · P264-P270-P301+P312-P330-P501-P280-P302+P352-P312-P322-P363-P501-P261-P271-P304+P340-P312
Hazard Codes
Xn
Risk Statements
25 · 25-20/21/22
Safety Statements
13 · 13-45-36
RIDADR
1544 · 1544
RTECS
8050000 · AX8050000
HazardClass
6.1 · 6.1(b)
PackingGroup
III
Toxicity
50 oral · LD50 oral in rat: 360mg/kg