Welcome to LookChem.com Sign In|Join Free

CAS

  • or

10097-84-4

Post Buying Request

10097-84-4 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

10097-84-4 Usage

Description

Different sources of media describe the Description of 10097-84-4 differently. You can refer to the following data:
1. Tetrahydropalmatine (THP) is an isoquinoline alkaloid found in in several different plant species, mainly in the Corydalis genus (Yan Hu Suo), but also in other plants such as Stephania rotunda (Qian Jin Teng). These plants exhibits analgesic, antinociceptive, anxiolytic, antidepressant, and anti-parasitic activities, and have traditional uses in Chinese herbal medicine. In particular, the levo isomer of THP (l-THP) appears to contribute to many of the therapeutic effects of these herbs. Notably, the dextro isomer of THP has distinct pharmacological actions that include depletion of monoamines and may contribute to the toxicology profile of THP-containing preparations or racemic mixtures of the compound. In addition to serving as an active constituent in traditional Chinese herbal preparations, purified or synthetic l-THP is approved for use and available as Rotundine or Rotundin in China, where l-THP has been used as an analgesic and sedative for more than 40 years.
2. The roots of Stephania rotunda furnish this alkaloid which forms colourless plates when crystallized from EtOH. It is laevorotatory with [α]23D - 262° (EtOH) and gives a crystalline hydrochloride with m.p. 258-9°C (dec.) and the methiodide which decomposes at that same temperature. Three methoxyl groups and one methyl group are present.

References

Different sources of media describe the References of 10097-84-4 differently. You can refer to the following data:
1. 1. https://en.wikipedia.org/wiki/Tetrahydropalmatine 2. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3878639/ 3.https://www.worldseedsupply.com/product/corydalis-yanhusuo-tetrahydropalmatine-98-pure-thp-isolate/ 4. https://www.lktlabs.com/product/dl-tetrahydropalmatine/
2. Kondo, Matsuno., J. Pharm. Soc., Japan, 64, (9A), 28 (1944)

Physical properties

Appearance: off-white solid, odorless, tasteless, and turns yellow under light and heat. It should be protected from light and air. Solubility: this product is usually dissolved in chloroform, slightly soluble in ethanol or ether, insoluble in water, and soluble in dilute sulfuric acid. Melting point: 141–144?°C. Specific optical rotation: ?290 to –300°.

History

From the 1920s, many researchers have focused on the alkaloid compounds contained in the Yan Hu Suo and extracted more than 30 different kinds of alkaloids. Among them Rotundine is one of the most important active compounds and has been successfully applied in clinical practice.Tetrahydropalmatine (THP) was firstly discovered by Zhao Chenggu, a famous medicinal phytochemist in China. He isolated 13 kinds of alkaloids and identified the structure of 6 of them. In 1936, Huang Minglong, a famous organic chemist, proved THP is a racemate. From 1933, Wang Jingxi and Lu Zihui began to study the pharmacological effects of THP and found that THP could induce catalepsy in animals. Rotundine is a levo-THP and obtained from the resolution of DL-THP during 1959–1964. From 1956 to 1965, the famous Chinese neuropharmacologist, Jin Guozhang, identified Rotundine as the main effective component in Yan Hu Suo and further studied its underlying mechanisms. He also found that Stephania contains abundant L-THP, which could become the source of clinical medication.In 1965, Rotundine was recorded in the textbooks of pharmacology. After over 20?years of clinical practices, people have proved that Rotundine has reliable efficacy and low side effect. In 1977, Rotundine was recorded in the Chinese Pharmacopoeia. In 1979, THP achieved a full synthesis, and currently Rotundine is mainly produced by artificial synthesis. From 1980, the study on the mechanisms of Rotundine made great progress. The analgesic effect of Rotundine has nothing to do with opioid receptors or prostaglandins. Rotundine does not belong to narcotic analgesics and antipyretic analgesics. Further, Rotundine has been found to have no affinity with M-cholinergic receptor and GABA system in the brain. But it has affinity to dopamine receptors. The exact mechanisms and pharmacology effects of Rotundine still need more research.

Uses

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

Pharmacology

1. Effects on the central nervous system: Rotundine has significant analgesic, sedative, and hypnotic effects, and its mechanism has nothing to do with opioid receptors. It has no obvious addiction effect. Using Rotundine combined with pethidine can enhance the analgesic effect, reduce the amount of pethidine, and further reduce the occurrence of drug dependence. The present study suggests that Rotundine is a central dopamine receptor blocker that inhibits the transmission of peripheral pain information by blocking the D2 receptor of the striatum and nucleus accumbens and the PAG-RgpI-spinal dorsal horn nerve pathway. In addition, Rotundine also has a suppression of the strengthening of the motor response induced by drug abuse, that is, inhibition of behavioral sensitization.2. Effects on the cardio-cerebrovascular system: Rotundine has inhibitory effect on the injuries caused by cerebral ischemia and reperfusion and myocardial ischemia and reperfusion. It also could lower the blood pressure. The pharmacological mechanism of Rotundine on the cardiovascular and cerebrovascular aspects is quite complex and may relate to the regulation of inflammation and inhibition of apoptosis. It is also found that Rotundine acts on α-receptors and has a noncompetitive antagonistic effect on calcium.3. Rotundine can reverse the drug resistance of tumor cells; the mechanism may be through the downregulating of the expression of P-glycoprotein (P-gp) and the upregulating of the expression of topo II in tumor cells.4. Rotundine has an excitatory effect on the endocrine system, such as the pituitaryadrenal system, and also has a protective effect on the liver.5. Drug metabolisms: The absorption of Rotundine by oral administration is complete. At 15?min it can be absorbed by 40–50%. It begins to work at 10–30?min, and the effect can last 2–5?h. In vivo distribution is through fat and the lung, liver, and kidney. If administered by subcutaneous injection, after 12?h, Rotundine will be discharged by 80% with the urine.

Clinical Use

1. Pain induced by gastrointestinal and hepatobiliary disorders, menstrual pain, and pain after childbirth.2. Mild trauma and postoperative pain3. Headache insomnia and spasmodic cough.4. There is a report about the usage of Rotundine in arrhythmia caused by I–III hypertension and other diseases.5. The hypnotic effect of Rotundine happens in 15?min after administration and then appears after 2?h. Because the analgesic effect happens at the same time, Rotundine is particularly suitable for insomnia patients with pain.6. Side effects: drowsiness, dizziness, fatigue, and nausea. Large dose of Rotundine can inhibit the respiratory center and may cause extrapyramidal symptoms.

Purification Methods

Crystallise it from MeOH or EtOH by addition of water [see Kametani & Ihara J Chem Soc (C) 530 1967, Bradsher & Dutta J Org Chem 26 2231 1961]. When crystallised from Me2CO/Et2O, it has m 142o. The hydrate has m 115o(effervescence). The picrate has m 188o(dec) (from aqueous EtOH). [Bradsher & Datta J Org Chem 26 2231 1961, Beilstein 21 II 196, 21 III/IV 2769.]

Check Digit Verification of cas no

The CAS Registry Mumber 10097-84-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,9 and 7 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 10097-84:
(7*1)+(6*0)+(5*0)+(4*9)+(3*7)+(2*8)+(1*4)=84
84 % 10 = 4
So 10097-84-4 is a valid CAS Registry Number.
InChI:InChI=1/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

10097-84-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrahydropalmatine

1.2 Other means of identification

Product number -
Other names D-Tetrahydropalmatin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10097-84-4 SDS

10097-84-4Relevant articles and documents

Studies on the alkaloids of Menispermaceous plants. 233. Alkaloids of Tinomiscium petiolare Miers

Tomita,Furutawa

, p. 881 - 882 (1967)

-

-

Schmutz

, p. 335,342 (1959)

-

Method for synthesizing tetrahydroberberine and derivatives thereof

-

Paragraph 0094-0099, (2021/07/08)

The invention provides a method for synthesizing tetrahydroberberine and derivatives thereof. Specifically, in the presence of an iridium metal catalyst precursor, a chiral diphosphine ligand, an acid and a halogen-containing additive, in a hydrogen atmosphere, a compound (II) is subjected to an asymmetric catalytic hydrogenation reaction in an organic solvent so as to prepare the compound (I).

Asymmetric synthesis of (S)-(-)-tetrahydropalmatine and (S)-(-)-canadine via a sulfinyl-directed Pictet-Spengler cyclization

Mastranzo, Virginia M.,Olivares Romero, José Luis,Yuste, Francisco,Ortiz, Benjamín,Sánchez-Obregón, Rubén,García Ruano, José L.

, p. 1266 - 1271 (2012/02/15)

(S)-(-)-Tetrahydropalmatine 2 and (S)-(-)-canadine 4 were synthesized in three steps from (S)-6, in 33% and 34% overall yield, respectively. Thus, condensation of the (S)-(E)-sulfinylimines 10 and 11 with the carbanion derived from (S)-6 gave the tetrahydroisoquinolines 12 and 13, respectively, which upon TFA induced N-desulfinylation, and subsequent microwave assisted Pictet-Spengler cyclization effected both cyclization and C-desulfinylation producing (S)-(-)-tetrahydropalmatine 2 and (S)-(-)-canadine 4 in optically pure form.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 10097-84-4