Lupanine - ≥96% , CAS No.550-90-3

CAS: 550-90-3 Cat. No.: L647118 Molecular Weight: 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

Overview

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

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,

Specifications & Purity

≥96%

Biochemical and Physiological Mechanisms

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

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥96%

Names and Identifiers

• Canonical Smiles: 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
• Isomeric SMILES: C1CCN2C[C@@H]3C[C@H]([C@@H]2C1)CN4[C@@H]3CCCC4=O
• PubChem CID: 91471
• Molecular Weight: 348.82

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: 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
• Description: 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

Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 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