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tetrahydropalmatine
13a-a-berbine, 2,3,9,10-tetramethoxy-

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CAS Number: 10097-84-4Picture of molecule3D/inchi
FDA UNII: 3X69CO5I79
Nikkaji Web:J31.887F
XlogP3-AA:3.20 (est)
Molecular Weight:355.43405000
Formula:C21 H25 N O4
BioActivity Summary:listing
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 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
Boiling Point: 482.87 °C. @ 760.00 mm Hg (est)
Flash Point: 282.00 °F. TCC ( 138.70 °C. ) (est)
logP (o/w): 0.591 (est)
Soluble in:
 water, 85.84 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.
Tetrahydropalmatin >98%
Odor: characteristic
Use: Rotundine, that is isolated from the root of Stephania tetrandra S. Moore, has significant effect of analgesia at 15min (P=0.022<0.05) and at 30min (P=0.022<0.05). It is ineffective in 60min. Rotundine may be a useful drug for suppressing morphine tolera Antinociceptive
Changsha Organic Herb
Corydalis Yanhusuo Extract
Coompo
For experimental / research use only.
Rotundine from Plants ≥98%
Odor: characteristic
Use: Rotundine at 20 mg/kg given subcutaneously (s.c.), which by itself did not produce any antinociceptive effect, significantly inhibited the development of tolerance. The physical dependence was evaluated in male rats. The behavioral signs including jumping, wet-dog shakes, teeth chattering, writhing, diarrhea, ptosis and vocalizing on touch, were observed. Withdrawal was precipitated by a single injection of naloxone in dependent rats. Rotundine (20 mg/kg, s.c.) suppressed jumping, teeth chattering, diarrhea and irritability but not other signs of physical dependence in the rat. The psychic dependence was assessed by the conditioned place preference in male mice. Rotundine (20 mg/kg s.c.), significantly attenuated the place preference induced by morphine. The results suggest that rotundine may be a useful drug for suppressing morphine tolerance and withdrawal symptoms. Rotundine has significant effect of analgesia at 15min (P=0.022<0.05) and at 30min (P=0.022<0.05). It is ineffective in 60min.Rotundine is used for producing tranquilliser with safe sleeping effect and without side-effects.
Nacalai USA
For experimental / research use only.
dl-Tetrahydropalmatine
Santa Cruz Biotechnology
For experimental / research use only.
L-Tetrahydropalmatine
 
Safety Information:
 
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:
intraperitoneal-mouse LD50 100 mg/kg
French Medicament Patent Document. Vol. #4818M

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for tetrahydropalmatine usage levels up to:
 not for fragrance use.
 
Recommendation for tetrahydropalmatine 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 :72301
National Institute of Allergy and Infectious Diseases:Data
(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
Chemidplus:0010097844
 
References:
 (13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):72301
Pubchem (sid):135076267
 
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
CHEMBL:View
KEGG (GenomeNet):C02890
HMDB (The Human Metabolome Database):Search
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
 corydalis yanhusuo
Search Trop Picture
 tithomia rotundifolia
Search Trop Picture
 
Synonyms:
13a-a-berbine, 2,3,9,10-tetramethoxy-
 caseanine
(-)-corydalis
6H-dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (S)-
6H-dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13aS)-
6h-dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-,(13as)-
 gindarine
 hyndarin
 hyndarine
 rotundine
(S)-5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine
5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo(a,g)quinolizine
5,8,13,13a(S)-tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g]quinolizine
(-)-tetrahydropalmatine
2,3,9,10-tetramethoxy-13aa-berbine
(13aS)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
(S)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline
(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
(S)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinoline
 

Articles:

PubMed:[Akaloids from roots of Stephania dentifolia].
PubMed:New antiplasmodial alkaloids from Stephania rotunda.
PubMed:Corylucinine, a new alkaloid from Corydalis cava (Fumariaceae), and its cholinesterase activity.
PubMed:[Chemical constituents from Corydalis yanhusuo].
PubMed:HPLC analysis of Stephania rotunda extracts and correlation with antiplasmodial activity
PubMed:Simultaneous determination of paeoniflorin, albiflorin, ferulic acid, tetrahydropalmatine, protopine, typhaneoside, senkyunolide I in Beagle dogs plasma by UPLC-MS/MS and its application to a pharmacokinetic study after Oral Administration of Shaofu Zhuyu Decoction.
PubMed:A practical strategy for characterization of the metabolic profile of chiral drugs using combinatory liquid chromatography-mass spectrometric techniques: application to tetrahydropalmatine enantiomers and their metabolites in rat urine.
PubMed:[Post-marketing clinical study of traditional Chinese medicine--lessons learned from comprehensive evaluation of Fufang Zaoren capsule].
PubMed:Application of quantitative 1H NMR for the calibration of protoberberine alkaloid reference standards.
PubMed:Oral administration of levo-tetrahydropalmatine attenuates reinstatement of extinguished cocaine seeking by cocaine, stress or drug-associated cues in rats.
PubMed:Tetrahydropalmatine inhibits pro-inflammatory mediators in lipopolysaccharide-stimulated THP-1 cells.
PubMed:Levo-tetrahydropalmatine attenuates cocaine self-administration under a progressive-ratio schedule and cocaine discrimination in rats.
PubMed:Levo-tetrahydropalmatine attenuates cocaine self-administration and cocaine-induced reinstatement in rats.
PubMed:[Chemical constituents from Corydalis humosa].
PubMed:The clinical spectrum of Jin Bu Huan toxicity.
 
Notes:
None found
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