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ajmaline
(17R,21-alpha)-ajmalan-17,21-diol

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CAS Number: 4360-12-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:224-439-4
FDA UNII: 1PON08459R
MDL:MFCD00135652
XlogP3:1.80 (est)
Molecular Weight:326.43962000
Formula:C20 H26 N2 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 206.00 °C. @ 760.00 mm Hg
Boiling Point: 519.40 °C. @ 760.00 mm Hg (est)
Flash Point: 545.00 °F. TCC ( 285.20 °C. ) (est)
logP (o/w): 1.810
Soluble in:
 water, 490 mg/L @ 30 °C (exp)
 water, 2486 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Ajmaline:Ajmalan-17,21-diol,(17R,21)-, 95%
Odor: characteristic
Use: Ajmaline is an alkaloid which could extracted from Rauwolfia serpentina. It is an antiarrhythmic agent, acting through changing the shreshold and the shape of cardiac action potentials. Ajmaline is an antiarrhythmic agent acting through changing the shreshold and the shape of cardiac action potentials
Carbosynth
For experimental / research use only.
Ajmaline
ExtraSynthese
For experimental / research use only.
Ajmaline (HPLC) ≥90%
Sigma-Aldrich: Sigma
For experimental / research use only.
Ajmaline
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50 178 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

oral-child LDLo 53125 ug/kg
GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Journal of Forensic Sciences. Vol. 33, Pg. 558, 1988.

intravenous-guinea pig LDLo 28 mg/kg
CARDIAC: CHANGE IN RATE
Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.

oral-man TDLo 32 mg/kg
CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE BEHAVIORAL: GENERAL ANESTHETIC LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Heart Journal. Vol. 70, Pg. 719, 1965.

intraperitoneal-mouse LD50 75 mg/kg
National Technical Information Service. Vol. AD691-490

intravenous-mouse LD50 21 mg/kg
European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975.

oral-mouse LD50 255 mg/kg
CARDIAC: CHANGE IN RATE
Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.

unreported-mouse LD50 220 mg/kg
Pharmaceutical Chemistry Journal Vol. 21, Pg. 331, 1987.

oral-quail LDLo 316 mg/kg
Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

intraperitoneal-rat LD50 94 mg/kg
Pharmaceutical Chemistry Journal Vol. 21, Pg. 331, 1987.

intravenous-rat LD50 26 mg/kg
CARDIAC: OTHER CHANGES
Pharmazie. Vol. 31, Pg. 36, 1976.

oral-rat LD50 360 mg/kg
BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Pharmazie. Vol. 31, Pg. 39, 1976.

Dermal Toxicity:
subcutaneous-mouse LD50 180 mg/kg
CARDIAC: CHANGE IN RATE
Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.

subcutaneous-rat LD50 216 mg/kg
CARDIAC: CHANGE IN RATE
Farmaco, Edizione Scientifica. Vol. 19, Pg. 865, 1964.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for ajmaline usage levels up to:
 not for fragrance use.
 
Recommendation for ajmaline flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :174236
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0004360127
RTECS:AX8050000 for cas# 4360-12-7
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):174236
Pubchem (sid):134985550
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
HMDB (The Human Metabolome Database):HMDB15495
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 rauwolfia serpentina root
Search Trop Picture
 
Synonyms:
 ajmalan-17,21-diol
(17R,21-alpha)-ajmalan-17,21-diol
(17R,21alpha)-ajmalan-17,21-diol
 ajmalan-17,21-diol, (17R,21-alpha)- (9CI)
 ajmalan-17,21-diol, (17R,21alpha)-, compound with methanol (1:1)
 ajmalin
 aritmina
 cardiorythmine
 cartagine
 gilurytmal
 ignazin
 merabitol
 raugalline
 rauwolfin
 rauwolfine
 rhytmaton
 ritmos
 rytmalin
 siddiqui
 tachmalin
 tajmalin
 takhmalin
 takycor
 

Articles:

PubMed:Investigation following resuscitated cardiac arrest.
PubMed:[Studies on predict of absorption of corynanthine, yohimbine, ajmalicine and ajmaline across human intestinal epithelial by using human Caco-2 cells monolayers].
PubMed:Purification, cloning, functional expression and characterization of perakine reductase: the first example from the AKR enzyme family, extending the alkaloidal network of the plant Rauvolfia.
PubMed:Structural biology in plant natural product biosynthesis--architecture of enzymes from monoterpenoid indole and tropane alkaloid biosynthesis.
PubMed:The structure of Rauvolfia serpentina strictosidine synthase is a novel six-bladed beta-propeller fold in plant proteins.
PubMed:Acetyltransfer in natural product biosynthesis--functional cloning and molecular analysis of vinorine synthase.
PubMed:Purification and partial amino acid sequences of the enzyme vinorine synthase involved in a crucial step of ajmaline biosynthesis.
PubMed:In vivo monitoring of alkaloid metabolism in hybrid plant cell cultures by 2D cryo-NMR without labelling.
PubMed:[Chagasic myocardiopathy: historical perspective].
PubMed:Inhibitory effects of plant secondary metabolites on cytotoxic activity of polymorphonuclear leucocytes.
PubMed:[Antiarrhythmic activity of ajmaline obtained from Rauwolfia serpentina biomass grown in tissue culture].
PubMed:[Clinical and electrophysiological aspects of median intra-His bundle block with normal electrocardiogram at rest].
PubMed:Usefulness of the ajmaline test in patients with latent bundle branch block.
PubMed:Unmasking of ventricular preexcitation by vagal stimulation or isoproterenol administration.
PubMed:Immobilized plant cells for the production and transformation of natural products.
 
Notes:
an alkaloid found in the root of rauwolfia serpentina, among other plant sources. it is a class ia antiarrhythmic agent that apparently acts by changing the shape and threshold of cardiac action potentials.
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