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Home > Encyclopedia > (-)-Tetrahydropalmatine

(-)-Tetrahydropalmatine

(-)-Tetrahydropalmatine structure

(-)-Tetrahydropalmatine 

structure
  • CAS No:

    483-14-7

  • Formula:

    C21H25NO4

  • Chemical Name:

    (-)-Tetrahydropalmatine

  • Synonyms:

    6H-Dibenzo[a,g]quinolizine,5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-,(13aS)-;13aα-Berbine,2,3,9,10-tetramethoxy-;Gindarine;6H-Dibenzo[a,g]quinolizine,5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-,(S)-;Cyclanoline,O,O-dimethyl-N-demethyl-;(13aS)-5,8,13,13a-Tetrahydro-2,3,9,10-tetramethoxy-6H-dibenzo[a,g]quinolizine;Caseanine;(-)-Tetrahydropalmatine;Hyndarine;Palmatine,tetrahydro-,(-)-;Rotundine;(-)-S-Tetrahydropalmatine;Rotundine (Stephania),(-)-;(-)-2,3,9,10-Tetramethoxyberbine;(-)-Rotundine;(S)-Tetrahydropalmatine;l-Tetrahydropalmatine;(-)-Corydalis B;N-Demethyl-O,O′-dimethylcyclanoline;N-Demethyl-O,O′-dimethylsteponine;(13AS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline;605-20-9;11075-91-5;34017-31-7;906324-96-7

  • Categories:

    Natural Products  >  Alkaloids

Description

Rotundine is an antagonist of dopamine D1, D2 and D3 receptors with IC50s of 166 nM, 1.4 μM and 3.3 μM, respectively. Rotundine is also an antagonist of 5-HT1A with an IC50 of 370 nM.


Tetrahydropalmatine is a berberine alkaloid obtained by formal addition of two molecules of hydrogen to the pyridine ring of palmatine. It has a role as an adrenergic agent, a non-narcotic analgesic and a dopaminergic antagonist. It is a berberine alkaloid and an organic heterotetracyclic compound. It derives from a palmatine.|Tetrahydropalmatine is under investigation in clinical trial NCT02118610 (Treatment of Schizophrenia With L-tetrahydropalmatine (l-THP): a Novel Dopamine Antagonist With Anti-inflammatory and Antiprotozoal Activity).

(-)-Tetrahydropalmatine Basic Attributes

355.434

355.43

3X69CO5I79

Characteristics

40.2

3.2

Off-white solid

1.2±0.1 g/cm3

142 °C

482.9°C at 760 mmHg

138.7±25.9 °C

1.609

Refrigerator

Safety Information

NONH for all modes of transport

HQ1792500

P264, P270, P301+P312, P330, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory.

Drug Information

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. (See all compounds classified as Anti-Arrhythmia Agents.)|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. (See all compounds classified as Antipsychotic Agents.)|A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)|A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)|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. (See all compounds classified as Antihypertensive Agents.)|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. (See all compounds classified as Adrenergic Agents.)|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. (See all compounds classified as Dopamine Antagonists.)

(+-)-isomer of tetrahydropalmatine

(-)-Tetrahydropalmatine Use and Manufacturing

An analgesic drug found in Chinese herbal medicine, used to treat heart disease and liver damage.

Computed Properties

Molecular Weight:355.4
XLogP3:3.2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:355.17835828
Monoisotopic Mass:355.17835828
Topological Polar Surface Area:40.2
Heavy Atom Count:26
Complexity:475
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Analgesic, sedative, anesthetic

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Recommended Suppliers of (-)-Tetrahydropalmatine

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    CAS No.: 483-14-7
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    Content: 99%
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