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Chemistry

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Also known as: Recinnamine, Reserpinene, Trimethoxycinnamoyl methyl reserpate, Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate, Ncgc00016787-01, 3,4,5-trimethoxycinnamoyl methyl reserpate
Molecular Formula
C35H42N2O9
Molecular Weight
634.7  g/mol
InChI Key
SZLZWPPUNLXJEA-LAFLMMDJSA-N

Rescinnamine
Rescinnamine is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia.
1 2D Structure

Rescinnamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
2.1.2 InChI
InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1
2.1.3 InChI Key
SZLZWPPUNLXJEA-LAFLMMDJSA-N
2.1.4 Canonical SMILES
COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC
2.1.5 Isomeric SMILES
CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=C4C=CC(=C5)OC)OC(=O)C=CC6=CC(=C(C(=C6)OC)OC)OC
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. Recinnamine

2. Reserpinene

3. Trimethoxycinnamoyl Methyl Reserpate

4. Methyl (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyloxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

5. Ncgc00016787-01

6. 3,4,5-trimethoxycinnamoyl Methyl Reserpate

7. Cas-24815-24-5

8. Prestwick0_000568

9. Prestwick1_000568

10. Dsstox_cid_3554

11. Dsstox_rid_77079

12. Dsstox_gsid_23554

13. Spbio_002575

14. Chembl3182071

15. Tox21_110611

16. Db01180

17. Q27164665

18. (1r,15s,17r,18r,19s,20s)-6,18-dimethoxy-17-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic Acid Methyl Ester

2.3 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 634.7 g/mol
Molecular Formula C35H42N2O9
XLogP34.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count10
Rotatable Bond Count11
Exact Mass634.28903092 g/mol
Monoisotopic Mass634.28903092 g/mol
Topological Polar Surface Area118 Ų
Heavy Atom Count46
Formal Charge0
Complexity1080
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count1
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of hypertension.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Used to treat hypertension. Rescinnamine inhibits angiotensin-converting enzyme. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor substance, angiotensin II. Angiotensin II also stimulates aldosterone secretion by the adrenal cortex and general vasoconstriction, both of which lead to increases vascular resistance. By inhibiting angiotensin II, aldosterone reabsorption is decreased as well as vasoconstriction. This combined effect serves to decrease blood pressure.


5.2 Mechanism of Action

Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.


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ABOUT THIS PAGE

Rescinnamine Manufacturers

A Rescinnamine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Rescinnamine, including repackagers and relabelers. The FDA regulates Rescinnamine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Rescinnamine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Rescinnamine Suppliers

A Rescinnamine supplier is an individual or a company that provides Rescinnamine active pharmaceutical ingredient (API) or Rescinnamine finished formulations upon request. The Rescinnamine suppliers may include Rescinnamine API manufacturers, exporters, distributors and traders.

click here to find a list of Rescinnamine suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Rescinnamine USDMF

A Rescinnamine DMF (Drug Master File) is a document detailing the whole manufacturing process of Rescinnamine active pharmaceutical ingredient (API) in detail. Different forms of Rescinnamine DMFs exist exist since differing nations have different regulations, such as Rescinnamine USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Rescinnamine DMF submitted to regulatory agencies in the US is known as a USDMF. Rescinnamine USDMF includes data on Rescinnamine's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Rescinnamine USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Rescinnamine suppliers with USDMF on PharmaCompass.

Rescinnamine GMP

Rescinnamine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Rescinnamine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Rescinnamine GMP manufacturer or Rescinnamine GMP API supplier for your needs.

Rescinnamine CoA

A Rescinnamine CoA (Certificate of Analysis) is a formal document that attests to Rescinnamine's compliance with Rescinnamine specifications and serves as a tool for batch-level quality control.

Rescinnamine CoA mostly includes findings from lab analyses of a specific batch. For each Rescinnamine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Rescinnamine may be tested according to a variety of international standards, such as European Pharmacopoeia (Rescinnamine EP), Rescinnamine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Rescinnamine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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