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492-08-0,MFCD00869353
Catalog No.:AA003BAK

492-08-0 | Pachycarpine

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1g
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$45.00   $32.00
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5g
97%
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$128.00   $90.00
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25g
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100g
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003BAK
Chemical Name:
Pachycarpine
CAS Number:
492-08-0
Molecular Formula:
C15H26N2
Molecular Weight:
234.3803
MDL Number:
MFCD00869353
SMILES:
C1CC[C@@H]2N(C1)C[C@H]1C[C@@H]2CN2[C@@H]1CCCC2
Properties
Properties
 
BP:
340.9°C at 760 mmHg  
Form:
Liquid  
MP:
201℃  
Refractive Index:
n/D1.527  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
263  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
2  
XLogP3:
2.5  

Literature

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Journal: Bioorganic & medicinal chemistry 20121001

Title: Asymmetric synthesis of trans-2,3-disubstituted indoline derivatives.

Journal: The Journal of organic chemistry 20120106

Title: [Derivatives of lupinin and epilupinin as ligands of various cholinesterases].

Journal: Zhurnal evoliutsionnoi biokhimii i fiziologii 20120101

Title: [Isomeric derivatives of lupinine and epilupinine--organophosphorus inhibitors of cholinesterases].

Journal: Ukrains'kyi biokhimichnyi zhurnal (1999 ) 20120101

Title: [Reversible lupininin inhibitors of cholinesterases of mammalian blood and of optical ganglia of individuals of the commander squid Berryteuthis magister from different zones of species areal].

Journal: Zhurnal evoliutsionnoi biokhimii i fiziologii 20120101

Title: Enantioselective, palladium-catalyzed α-arylation of N-Boc pyrrolidine: in situ react IR spectroscopic monitoring, scope, and synthetic applications.

Journal: The Journal of organic chemistry 20110805

Title: Total syntheses of (-) epilupinine and (-)-tashiromine using imino-aldol reactions.

Journal: Organic letters 20110805

Title: Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.

Journal: Journal of medicinal chemistry 20110714

Title: Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.

Journal: The Journal of organic chemistry 20110415

Title: Total synthesis of (+)-epilupinine via an intramolecular nitrile oxide-alkene cycloaddition.

Journal: The Journal of organic chemistry 20110107

Title: Development and application of a method to investigate drug-metabolizing enzyme inhibitors using sparteine for probe of cytochrome P450 2D6 and tris(2,2'-bipyridine)ruthenium(II)-electrogenerated chemiluminescence detection.

Journal: Chemical & pharmaceutical bulletin 20110101

Title: Experimental and computational study of a direct O2-coupled Wacker oxidation: water dependence in the absence of Cu salts.

Journal: Journal of the American Chemical Society 20100901

Title: Can the genotype or phenotype of two polymorphic drug metabolising cytochrome P450-enzymes identify oral lichenoid drug eruptions?

Journal: Journal of oral pathology & medicine : official publication of the International Association of Oral Pathologists and the American Academy of Oral Pathology 20100701

Title: Characterization of a rhodium-sparteine complex, [((-)-sparteine)Rh(eta4-COD)]+: crystal structure and DNMR/DFT studies on ligand-rotation dynamics.

Journal: Dalton transactions (Cambridge, England : 2003) 20100321

Title: Short access to (+)-lupinine and (+)-epiquinamide via double hydroformylation.

Journal: Organic letters 20100205

Title: Asymmetric catalysis of homo-coupling of 3-substituted naphthylamine and hetero-coupling with 3-substituted naphthol leading to 3,3'-dimethyl-2,2'-diaminobinaphthyl and -2-amino-2'-hydroxybinaphthyl.

Journal: Chirality 20100201

Title: Estimation of the interindividual variability of cytochrome 2D6 activity from urinary metabolic ratios in the literature.

Journal: Drug metabolism and pharmacokinetics 20100101

Title: Reactions of (-)-sparteine with alkali metal HMDS complexes: conventional meets the unconventional.

Journal: Chemical communications (Cambridge, England) 20091021

Title: Optically active (aR)- and (aS)-linear and vaulted biaryl ligands: deracemization versus oxidative dimerization.

Journal: Journal of the American Chemical Society 20091014

Title: Enantiomerization dynamics and a catalytic dynamic resolution of N-trimethylallyl-2-lithiopyrrolidine.

Journal: Journal of the American Chemical Society 20090527

Title: Epiquinamide: a poison that wasn't from a frog that was.

Journal: Journal of natural products 20090227

Title: Total synthesis of (+/-)-alpha-isosparteine, (+/-)-beta-isosparteine, and (+/-)-sparteine from a common tetraoxobispidine intermediate.

Journal: The Journal of organic chemistry 20081017

Title: A new catalytic Cu(II)/sparteine oxidant system for beta,beta-phenolic couplings of styrenyl phenols: synthesis of carpanone and unnatural analogs.

Journal: Organic letters 20080918

Title: A direct stereoselective approach to trans-2,3-disubstituted piperidines: application in the synthesis of 2-Epi-CP-99,994 and (+)-epilupinine.

Journal: Organic letters 20080619

Title: A new sparteine surrogate for asymmetric deprotonation of N-Boc pyrrolidine.

Journal: Organic letters 20080403

Title: Basic instinct: design, synthesis and evaluation of (+)-sparteine surrogates for asymmetric synthesis.

Journal: Chemical communications (Cambridge, England) 20080214

Title: Asymmetric lithiation-substitution of amines involving rearrangement of borates.

Journal: Organic letters 20080103

Title: Cholinesterase hydrolysis of substituted lupinine benzoates.

Journal: Doklady. Biochemistry and biophysics 20080101

Title: Bactericidal and fungicidal activities of Calia secundiflora (Ort.) Yakovlev.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101

Title: Stereocontrolled synthesis and alkylation of cyclic beta-amino esters: asymmetric synthesis of a (-)-sparteine surrogate.

Journal: Organic & biomolecular chemistry 20071121

Title: A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties.

Journal: The Journal of organic chemistry 20070803

Title: A natural variant of the heme-binding signature (R441C) resulting in complete loss of function of CYP2D6.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20070801

Title: Hypoglycaemic effect of quinolizidine alkaloids--lupanine and 2-thionosparteine on non-diabetic and streptozotocin-induced diabetic rats.

Journal: European journal of pharmacology 20070622

Title: [Phenotypes of oxidation and acetylation in Alzheimer's disease--preliminary report].

Journal: Psychiatria polska 20070101

Title: Enantioselective nitroaldol (Henry) reaction using copper(II) complexes of (-)-sparteine.

Journal: Chemical communications (Cambridge, England) 20061021

Title: Neuronal damage and changes in the expression of muscarinic acetylcholine receptor subtypes in the neonatal rat cerebral cortical upon exposure to sparteine, a quinolizidine alkaloid.

Journal: International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20061001

Title: Pd(II)-catalyzed conversion of styrene derivatives to acetals: impact of (-)-sparteine on regioselectivity.

Journal: Organic letters 20060316

Title: Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation.

Journal: Journal of the American Chemical Society 20060315

Title: Asymmetric synthesis of 4,5,6- and 3,4,5,6-substituted azepanes by a highly diastereoselective and enantioselective lithiation-conjugate addition sequence.

Journal: Journal of the American Chemical Society 20060222

Title: [Clinical significance of oxidation and acetylation genetic polymorphism in patients with hyperthyreosis].

Journal: Endokrynologia Polska 20060101

Title: Origin of enantioselection in chiral alcohol oxidation catalyzed by Pd[(-)-sparteine]Cl2.

Journal: Journal of the American Chemical Society 20051026

Title: A practical synthesis of (+/-)-alpha-isosparteine from a tetraoxobispidine core.

Journal: Organic letters 20051013

Title: Stereocontrolled total synthesis of (-)-kainic acid. Regio- and stereoselective lithiation of pyrrolidine ring with the (+)-sparteine surrogate.

Journal: Organic letters 20050929

Title: Enantioselective lithiation of O-alkyl and O-alk-2-enyl Carbamates in the presence of (-)-sparteine and (-)-alpha-isosparteine. A theoretical study.

Journal: The Journal of organic chemistry 20050527

Title: Cascade iminium ion reactions for the facile synthesis of quinolizidines. Concise syntheses of (+/-)-epilupinine and (-)-epimyrtine.

Journal: Organic letters 20050512

Title: A synthesis of (+/-)-sparteine.

Journal: Organic & biomolecular chemistry 20050421

Title: Absolute configuration of 2-(tributylstannyl)pyrrolidine by anomalous dispersion X-ray analysis.

Journal: The Journal of organic chemistry 20050107

Title: [Synthesis of lupinine derivatives of flavonoids].

Journal: Bioorganicheskaia khimiia 20050101

Title: Is the A-ring of sparteine essential for high enantioselectivity in the asymmetric lithiation-substitution of N-Boc-pyrrolidine?

Journal: Journal of the American Chemical Society 20041201

Title: An experimental and computational study of the enantioselective lithiation of N-Boc-pyrrolidine using sparteine-like chiral diamines.

Journal: Journal of the American Chemical Society 20041201

Title: Comparison of plasma disposition of alkaloids after lupine challenge in cattle that had given birth to calves with lupine-induced arthrogryposis or clinically normal calves.

Journal: American journal of veterinary research 20041101

Title: Total synthesis of (-)-alpha-kainic acid by (-)-sparteine-mediated asymmetric deprotonation-cycloalkylation.

Journal: Organic letters 20041014

Title: Effect of ligand structure on the asymmetric cyclization of achiral olefinic organolithiums.

Journal: The Journal of organic chemistry 20040903

Title: Synthesis of a new N-acetyl thiazolidinethione reagent and its application to a highly selective asymmetric acetate aldol reaction.

Journal: Organic letters 20040902

Title: Concise asymmetric synthesis of (-)-sparteine.

Journal: Chemical communications (Cambridge, England) 20040821

Title: Evaluation of (+)-sparteine-like diamines for asymmetric synthesis.

Journal: The Journal of organic chemistry 20040820

Title: A short synthesis of (+/-)-cytisine.

Journal: Organic & biomolecular chemistry 20040707

Title: Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20040705

Title: A computational model relating structure and reactivity in enantioselective oxidations of secondary alcohols by (-)-sparteine-Pd(II) complexes.

Journal: Journal of the American Chemical Society 20040630

Title: [Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].

Journal: Zhurnal evoliutsionnoi biokhimii i fiziologii 20040101

Title: Palladium-catalyzed aerobic oxidative kinetic resolution of alcohols with an achiral exogenous base.

Journal: The Journal of organic chemistry 20030919

Title: Mechanistic investigations of the palladium-catalyzed aerobic oxidative kinetic resolution of secondary alcohols using (-)-sparteine.

Journal: Journal of the American Chemical Society 20030611

Title: Scope of enantioselective palladium(II)-catalyzed aerobic alcohol oxidations with (-)-sparteine.

Journal: The Journal of organic chemistry 20030530

Title: Synthetic applications of lithiated N-Boc allylic amines as asymmetric homoenolate equivalents.

Journal: The Journal of organic chemistry 20030221

Title: Homology modeling of rat and human cytochrome P450 2D (CYP2D) isoforms and computational rationalization of experimental ligand-binding specificities.

Journal: Journal of medicinal chemistry 20030102

Title: Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.

Journal: Doklady. Biochemistry and biophysics 20030101

Title: A readily-accessible (+)-sparteine surrogate.

Journal: Journal of the American Chemical Society 20021009

Title: Enantioselective synthesis of 2-substituted 2-phenylethylamines by lithiation-substitution sequences: synthetic development and mechanistic pathway.

Journal: The Journal of organic chemistry 20020920

Title: Control of the conformational equilibria in aza-cis-decalins: structural modification, solvation, and metal chelation.

Journal: The Journal of organic chemistry 20020906

Title: First asymmetric total synthesis of (+)-sparteine.

Journal: Organic letters 20020725

Title: Practical and highly selective oxazolidinethione-based asymmetric acetate aldol reactions with aliphatic aldehydes.

Journal: Organic letters 20020627

Title: Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

Journal: Phytochemistry 20020601

Title: Lobocyclamide B from Lyngbya confervoides. Configuration and asymmetric synthesis of beta-hydroxy-alpha-amino acids by (-)-sparteine-mediated aldol addition.

Journal: Organic letters 20020530

Title: Conformational control of flexible molecules: design and synthesis of novel chiral 1,5-diaza-cis-decalins.

Journal: The Journal of organic chemistry 20020503

Title: Bacterial removal of quinolizidine alkaloids and other carbon sources from a Lupinus albus aqueous extract.

Journal: Journal of agricultural and food chemistry 20020410

Title: Acute hypoxia and cytochrome P450-mediated hepatic drug metabolism in humans.

Journal: Clinical pharmacology and therapeutics 20020401

Title: An experimental and computational investigation of the enantioselective deprotonation of Boc-piperidine.

Journal: Journal of the American Chemical Society 20020306

Title: Effect of growth hormone on hepatic cytochrome P450 activity in healthy elderly men.

Journal: Clinical pharmacology and therapeutics 20020301

Title: Pharmacokinetics of therapeutic doses of tropisetron in healthy volunteers.

Journal: British journal of clinical pharmacology 20011201

Title: Dose-dependent inhibition of the CYP2D6 catalyzed oxidation of sparteine by mepyramine in healthy volunteers.

Journal: Pharmacology & toxicology 20011201

Title: Inhibition of cytochrome P4502D6 activity with paroxetine normalizes the ultrarapid metabolizer phenotype as measured by nortriptyline pharmacokinetics and the debrisoquin test.

Journal: Clinical pharmacology and therapeutics 20011001

Title: Indolizidine and quinolizidine alkaloids.

Journal: Natural product reports 20011001

Title: Chiral diamines 4: a computational study of the enantioselective deprotonation of Boc-pyrrolidine with an alkyllithium in the presence of a chiral diamine.

Journal: Journal of the American Chemical Society 20010829

Title: Absorption and disposition of levocetirizine, the eutomer of cetirizine, administered alone or as cetirizine to healthy volunteers.

Journal: Fundamental & clinical pharmacology 20010801

Title: Influence of CYP2D6 genotype and medication on the sparteine metabolic ratio of psychiatric patients.

Journal: European journal of clinical pharmacology 20010701

Title: Kinetics and mechanism of the (-)-sparteine-mediated deprotonation of (E)-N-Boc-N-(p-methoxyphenyl)-3-cyclohexylallylamine.

Journal: Journal of the American Chemical Society 20010530

Title: Novel sparteine-mediated enantio-dichotomic formal synthesis of R-(-)- and S-(+)-curcuphenol.

Journal: The Journal of organic chemistry 20010420

Title: Synthesis of enantiomerically enriched allenes by (-)-sparteine-mediated lithiation of alkynyl carbamates.

Journal: Organic letters 20010419

Title: Moving toward genetic profiling in patient care: the scope and rationale of pharmacogenetic/ecogenetic investigation.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20010401

Title: 2-(4-R-phenoxy/phenylthio)alkanoic esters of l-lupinine.

Journal: Farmaco (Societa chimica italiana : 1989) 20010301

Title: Asymmetric aldol additions: use of titanium tetrachloride and (-)-sparteine for the soft enolization of N-acyl oxazolidinones, oxazolidinethiones, and thiazolidinethiones.

Journal: The Journal of organic chemistry 20010209

Title: Immunolocalization of alkaloids and X-ray microanalysis of elements in lupin seeds.

Journal: Protoplasma 20010101

Title: Drug metabolism and genetic polymorphism in subjects with previous halothane hepatitis.

Journal: Scandinavian journal of gastroenterology 19930801

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Severe complications of antianginal drug therapy in a patient identified as a poor metabolizer of metoprolol, propafenone, diltiazem, and sparteine.

Journal: Klinische Wochenschrift 19871215

Title: Screening for new compounds with antiherpes activity.

Journal: Antiviral research 19841001

Title: Antifibrillatory, cardiovascular and toxic effects of sparteine, butylsparteine and pentylsparteine.

Journal: Arzneimittel-Forschung 19800101

Title: [Effect of sparteine sulfate on the predamaged conduction system of the heart].

Journal: Zeitschrift fur Kardiologie 19750501

Title: Voitenko S, et al. Effect of (+)-sparteine on nicotinic acetylcholine receptors in the neurons of rat superior cervical ganglion. Mol Pharmacol. 1991 Aug;40(2):180-5.

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Tags:492-08-0 Molecular Formula|492-08-0 MDL|492-08-0 SMILES|492-08-0 Pachycarpine