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Rotundine

HCID 5417
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Basic information

CAS
2934-97-6
Standard SMILES
COc1cc2c(cc1OC)C1Cc3ccc(OC)c(OC)c3CN1CC2
InChIKey
AEQDJSLRWYMAQI-UHFFFAOYSA-N
Molecular formula
C21H25NO4
Average molar mass
355.4 g/mol
Monoisotopic mass
355.17835828

Overview

2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline is an alkaloid.

Names & identifiers

Preferred name
Rotundine
IUPAC
2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline
English name
Tetrahydropalmatine
Molecular formula
C21H25NO4
Molecular weight
355.43

Names & synonyms

RotundineRefChem:9309042934-97-610097-84-4ROTUNDINUMD,L-Tetrahydropalmatine2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolineTetrahydropalmatine, (+/-)-CHEMBL18789278F8583LNQ2,3,9,10-Tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[3,2-a]isoquinolineMFCD00214191
Show more names
L-TETRAHYDROPALMATINEDL-TETRAHYDROPALMATINEAKOS 208-04ROTUNDIN HYDRATERotundine CP2000TetrahydropalmatineTETRAHYDROPALMITINERafoxanide Impurity 5Tetrahydropalmatine-RM
Tetrahydropalmatine, dl-2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolinePalmatine, Tetrahydro derivative of2,3,9,10-Tetramethoxy-5,8,13,13a-tetrahydro-6H-isoquinolino[3,2-a]isoquinolineD-Tetrahydropalmatin; Rotundine; 5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g] quinolizineUNII-78F8583LNQRotundine [M+H]+(-)-Tetrahydropalmatine;L-Tetrahydropalmatine

Database identifiers

CAS
2934-97-6
PubChem CID
5417
DTXSID
DTXSID20864207
ChEMBL
CHEMBL187892
ChEBI
CHEBI:91709
UNII
78F8583LNQ
EC Number
884-574-5
Nikkaji
J31.846I

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
40.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
26
Formal charge
0
Complexity
475

Experimental & physicochemical properties

LogP2.6

Physicochemical properties

Melting point
155 ℃ · 155℃
Boiling point
482.9 · 482.9±45.0 °C(Predicted)
Density
1.23 · 1.23±0.1 g/cm3(Predicted)
storage temp.
Sealed in dry,Room Temperature
solubility
Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
form
Solid
pka
6.53 · 6.53±0.20(Predicted)
color
White to Pale Yellow
FDA UNII
78 F8583LNQ · 78F8583LNQ
HS Code
29339900 · 29339900

Safety & regulation

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

GHS classification

GHS Classification · 4 items

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Safety data

hs_code
29339900

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 6 items

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

A class of drugs that act by selective inhibition of calcium influx through cellular membranes.

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters.

Applications · 4 items

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

DescriptionTetrahydropalmatine can be prepared from the total bases of tetrahydroxy berberine. Tetrahydropalmatine can be used to prepare palmatine. Palmatine has a broad-spectrum antibacterial effect, especially against Candida albicans. It can be used clinically to treat gynecological inflammation, bacillary dysentery, enteritis, respiratory and urinary tract infections, surgical infections, and conjunctivitis. Palmatine can also enhance the relaxation of the body's norepinephrine smooth muscle. Tetrahydropalmatine, an active component isolated from corydalis, acts through inhibition of amygdaloid release of dopamine to inhibit an epileptic attack in rats.

UsesDL-Tetrahydropalmatine is the main active substance of the Chinese herb corydalis which induces hypotension and bradycardia in rats through the antagonism of striatal dopamine D2 receptor.

Usesanalgesic, hypnotic, papaverine-like

UsesDL-Tetrahydropalmatine is the main active substance of the Chinese herb corydalis which induces hypotension and bradycardia in rats through the antagonism of striatal dopamine D2 receptor.

Preparation methods · 1 item

PreparationA. Berberine hydrochloride is ring-opened under the conditions of p-toluenesulfonic acid, xylene, and HCl at 70°C to obtain desmethylene berberine hydrochloride.B. Demethylene berberine hydrochloride is methyl etherified with potassium carbonate, methanol, and dimethyl sulfate at 40°C to obtain palmatine hydrochloride.C. Palmatine hydrochloride is racemized under the conditions of methanol and sodium borohydride to obtain tetrahydropalmatine.

Upstream & downstream products

Upstream raw materials

8H-Dibenzo[a,g]quinolizin-8-one, 5,6,13,13a-tetrahydro-2,3,9,10-tetramethoxy-Dihydropalmatine

Additional notes

DefinitionChEBI: 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline is an alkaloid.