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Chemistry

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Also known as: 480-85-3, Senecifolinene, Retronecin, (+)-retronecine, Ccris 5776, (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol
Molecular Formula
C8H13NO2
Molecular Weight
155.19  g/mol
InChI Key
HJSJELVDQOXCHO-HTQZYQBOSA-N
FDA UNII
2P5723M6II

Retronecine
retronecine is a natural product found in Senecio nebrodensis, Senecio squalidus, and other organisms with data available.
1 2D Structure

Retronecine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol
2.1.2 InChI
InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1
2.1.3 InChI Key
HJSJELVDQOXCHO-HTQZYQBOSA-N
2.1.4 Canonical SMILES
C1CN2CC=C(C2C1O)CO
2.1.5 Isomeric SMILES
C1CN2CC=C([C@@H]2[C@@H]1O)CO
2.2 Other Identifiers
2.2.1 UNII
2P5723M6II
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Heliotridine

2. Retronecine, (1s-cis)-isomer

3. Retronecine, Monohydrochloride, (1s-cis)-isomer

4. Retronecine, Monohydrochloride, (1s-trans)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 480-85-3

2. Senecifolinene

3. Retronecin

4. (+)-retronecine

5. Ccris 5776

6. (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol

7. (1r,8r)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1h-pyrrolizin-1-ol

8. 2p5723m6ii

9. (1r,7ar)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizine-7-methanol

10. ( )-retronecine

11. Hsdb 3567

12. Unii-2p5723m6ii

13. Retronecine [mi]

14. 1h-pyrrolizine-7-methanol, 2,3,5,7a-beta-tetrahydro-1-alpha-hydroxy-

15. Retronecine [hsdb]

16. Schembl673883

17. Chebi:8821

18. Retronecine, Analytical Standard

19. Dtxsid401020156

20. Hy-n8419

21. Zinc1996064

22. Mfcd01684783

23. Stl564628

24. 1h-pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1r-trans)-

25. Akos003672869

26. Cs-0144131

27. C06177

28. Q3933789

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 155.19 g/mol
Molecular Formula C8H13NO2
XLogP3-1.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass155.094628657 g/mol
Monoisotopic Mass155.094628657 g/mol
Topological Polar Surface Area43.7 Ų
Heavy Atom Count11
Formal Charge0
Complexity191
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

Lactating rats dosed with (3)H-retronecine excreted within 3 hr approx 0.08% of the applied radioactivity in the milk mainly as yet not identified water soluble retronecine-derived metabolites and approx 0.02% as unchanged pyrrolizidine alkaloids (pas). Highest tissue levels of pas and metabolites, 6 hr after admin were found in liver and lungs.

PMID:6623523 Luthy J et al; Toxicol Lett 17(3-4): 283 (1983)


4.2 Metabolism/Metabolites

Steric hindrance around the ester groups was the major factor inhibiting hydrolysis of pyrrolizidine alkaloids. Enzymic hydrolysis of retronecine di-isovalerate occurred primarily at the allylic 9-ester group. The results supported the view that a factor contributing to the lower hepatotoxicity of semisynthetic retronecine diesters compared with some natural pyrrolizidine alkaloids, is their greater susceptibility to detoxication by hydrolysis.

Mattocks A; Toxicol Lett 14(1-2) 111 (1982)


Levels of pyrrolic metabolites were measured in the livers of rats given some pyrrolizidine alkaloids and semisynthetic derivatives. Structural and chemical features favoring the formation of such metabolites were defined. The most important of these were steric hindrance or chemical properties giving resistance to ester hydrolysis; lipophilic character, allowing access to hepatic microsomal enzymes; a conformation favoring microsomal oxidation of the pyrroline ring in preference to n-oxidation.

PMID:7226276 Mattocks A; Chem-Biol Interact 35(3): 301 (1981)


Levels of pyrrolic metabolites were measured in the livers of rats given some pyrrolizidine alkaloids and semisynthetic derivatives. ... Heliotridine-based alkaloids gave more pyrrole than similar retronecine esters, heliotridine ditiglate gave less pyrrole than retronecine ditiglate because the former was more open to hydrolytic attack.

PMID:7226276 Mattocks AR; Chem-Biol Interact 35(3): 301-310 (1981)


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

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Retronecine manufacturer or Retronecine supplier.

PharmaCompass also assists you with knowing the Retronecine API Price utilized in the formulation of products. Retronecine API Price is not always fixed or binding as the Retronecine Price is obtained through a variety of data sources. The Retronecine Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Retronecine

Synonyms

480-85-3, Senecifolinene, Retronecin, (+)-retronecine, Ccris 5776, (1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol

Cas Number

480-85-3

Unique Ingredient Identifier (UNII)

2P5723M6II

About Retronecine

retronecine is a natural product found in Senecio nebrodensis, Senecio squalidus, and other organisms with data available.

Retronecine Manufacturers

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

Retronecine Suppliers

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

Retronecine GMP

Retronecine 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 Retronecine 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 Retronecine GMP manufacturer or Retronecine GMP API supplier for your needs.

Retronecine CoA

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

Retronecine CoA mostly includes findings from lab analyses of a specific batch. For each Retronecine 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.

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