Lupanine - ≥96% , CAS No.550-90-3

CAS: 550-90-3 Cat. No.: L647118 Summenformel: C₁₅H₂₄N₂O Molekulargewicht: 348.82 PubChem CID: 91471

GRADE & PURITY ≥96%

Synonyms

Lupanine d-form | MFCD00220969 | 3-(2,4-DICHLOROPHENYL)PROPIONICACID | SMR000062994 | LUPANINE DL-FORM [MI] | 9K48888N9P | (7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol(1,2-a:1',2'-e)(1,5)diazocin-11-one | AT20203 | Ethanone,

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Übersicht

Lupanine (D-Lupanine) is a natural ketonic derivative of Sparteine ( (+)-Sparteine ) with a ganglioplegic activity. Lupanine shows binding affinity for nicotinic receptor ( nAChR ) with a K i value of 500 nM

In Vitro

Lupanine shows binding affinity for nicotinic receptor with a K i value of 500 nM. While, Lupanine shows a very weak affinity for the muscarinic receptor with a K i value of 11000 nM. Lupanine (0-100 μM) is a weak agonist and desensitizer in SH-SY5Y cells, with EC 50 and DC 50 of 10.7 μM and 28.2 μM, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Lupanine (100-300 mg/kg for i.p.; 175-700 mg/kg for p.o.) is much less toxic in one single injection in EOPS male Swiss mice (20-22 g) and Hartley guinea-pigs (400-500 g) . Lupanine (1-7.5 mg/kg; i.v.) is more efficient than Sparteine for antagonizing secondary reflex hypertension in carotid occlusion and hypotension resulting from the stimulation of the pneumogastric nerve in both the cat and the dog . Lupanine has an inhibitory action on nicotinic type hypertension produced by injection of Acetylcholine (500 p.g/kg i.v.) in the Atropine-treated dog . MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Liquid

IC50& Target:Ki: 500 nM (Nicotinic receptor) and 11000 nM (Muscarinic receptor)

Specifications

Synonyme

Lupanine d-form | MFCD00220969 | 3-(2,4-DICHLOROPHENYL)PROPIONICACID | SMR000062994 | LUPANINE DL-FORM [MI] | 9K48888N9P | (7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol(1,2-a:1',2'-e)(1,5)diazocin-11-one | AT20203 | Ethanone,

Spezifikationen & Reinheit

≥96%

Biochemische und physiologische Mechanismen

Lupanine (D-Lupanine) is a natural ketonic derivative of Sparteine ( (+)-Sparteine ( HY-W008350 ) ) with a ganglioplegic activity. Lupanine shows binding affinity for nicotinic receptor ( nAChR ) with a K i value of 500 nM.

Storage

Protected from light,Store at -80°C

Verschickt in

Dry ice packs + Cold packs

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Aktionsart

INHIBITOR

Reinheit

≥96%

Namen und Kennungen

Kanonisches Lächeln

C1CCN2CC3CC(C2C1)CN4C3CCCC4=O

IUPAC Name

(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one

InChIKey

JYIJIIVLEOETIQ-XDQVBPFNSA-N

INCHI

1S/C15H24N2O/c18-15-6-3-5-14-11-8-12(10-17(14)15)13-4-1-2-7-16(13)9-11/h11-14H,1-10H2/t11-,12-,13-,14+/m0/s1

Isomere SMILES

C1CCN2C[C@@H]3C[C@H]([C@@H]2C1)CN4[C@@H]3CCCC4=O

PubChem CID

91471

Molekulargewicht

348.82

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Klasse Lupin alkaloids
      • Subclass Sparteine, lupanine, and related alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Klasse: Lupin alkaloids
• Subclass: Sparteine, lupanine, and related alkaloids
• Intermediate Tree Nodes: Not available
• Direct Parent: Sparteine, lupanine, and related alkaloids
• Alternative Parents: Quinolizidinones Piperidinones Delta lactams Tertiary carboxylic acid amides Trialkylamines Amino acids and derivatives Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Sparteine-lupanine skeleton - Quinolizidinone - Quinolizidine - Delta-lactam - Piperidinone - Piperidine - Tertiary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Lactam - Tertiary amine - Tertiary aliphatic amine - Azacycle - Carboxylic acid derivative - Organoheterocyclic compound - Organic nitrogen compound - Amine - Organooxygen compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Hydrocarbon derivative - Aliphatic heteropolycyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as sparteine, lupanine, and related alkaloids. These are alkaloids with a structure based on either sparteine, lupanine, or derivatives thereof. These are tetracyclic compounds made of two fused quinolizidine ring systems.
• External Descriptors: tertiary amine - quinolizidine alkaloid - delta-lactam

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Wirkungsmechanismen

Chemische und physikalische Eigenschaften

• Molekulargewicht: 248.360 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 248.189 Da
• Monoisotopic Mass: 248.189 Da
• Topological Polar Surface Area: 23.600 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 356.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥96% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?80 °C, protected from light. The material is light-sensitive — keep it in its original opaque or amber container.

How is this product shipped?

This product ships frozen with dry ice and cold packs. Unpack on arrival and transfer it to the storage condition stated above; handle dry ice with insulated gloves in a ventilated area.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 550-90-3, the molecular formula is C15H25ClN2O5, and the molecular weight is 348.82 g/mol. InChIKey JYIJIIVLEOETIQ-XDQVBPFNSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.