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(+/-)-Narwedine, also known as the biogenetic precursor of galanthamine, is a naturally occurring compound with various pharmacological properties. It has been studied for its potential as a respiratory stimulator and its ability to influence cardiac contractions, making it a promising candidate for various medical applications.

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  • 1668-86-6 Structure
  • Basic information

    1. Product Name: (+/-)-Narwedine
    2. Synonyms: (4aR;12-hexahydro-3-Methoxy-11-Methyl-;2-ef][2]benzazepin-6-one;6H-Benzofuro[3a;8aR)-rel-;GalantaMine interMediate (dl-Narwedine);Narwedine,racemic;(+/-)-3-Deoxy-3-oxogalanthamine
    3. CAS NO:1668-86-6
    4. Molecular Formula: C17H19NO3
    5. Molecular Weight: 285.341
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1668-86-6.mol
  • Chemical Properties

    1. Melting Point: 198-199 °C(Solv: ethyl acetate (141-78-6))
    2. Boiling Point: 397.388 °C at 760 mmHg
    3. Flash Point: 194.134 °C
    4. Appearance: /
    5. Density: 1.28
    6. Vapor Pressure: 1.59E-06mmHg at 25°C
    7. Refractive Index: 1.626
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 7.84±0.20(Predicted)
    11. CAS DataBase Reference: (+/-)-Narwedine(CAS DataBase Reference)
    12. NIST Chemistry Reference: (+/-)-Narwedine(1668-86-6)
    13. EPA Substance Registry System: (+/-)-Narwedine(1668-86-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1668-86-6(Hazardous Substances Data)

1668-86-6 Usage

Uses

Used in Respiratory Applications:
(+/-)-Narwedine is used as a respiratory stimulator to increase the amplitude of respiratory movements, which can be beneficial in treating conditions that require enhanced respiratory function.
Used in Cardiac Applications:
(+/-)-Narwedine is used to decrease the frequency of cardiac contractions, which can be valuable in reducing blood loss during surgery by promoting a more controlled and stable heart rate.
Used in Anesthesia and Pain Management:
(+/-)-Narwedine is used to inhibit the action of narcotics and hypnotics, making it a potential candidate for improving the effectiveness of anesthesia during surgical procedures. Additionally, it increases the analgesic effect of morphine, enhancing pain management in patients.
Used in Enhancing Pharmacological Effects:
(+/-)-Narwedine is used to increase the pharmacological effects of various substances, such as caffeine, carbazole, arecoline, and nicotine. This property can be beneficial in optimizing the therapeutic outcomes of these compounds in different medical applications.

Check Digit Verification of cas no

The CAS Registry Mumber 1668-86-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,6,6 and 8 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1668-86:
(6*1)+(5*6)+(4*6)+(3*8)+(2*8)+(1*6)=106
106 % 10 = 6
So 1668-86-6 is a valid CAS Registry Number.
InChI:InChI=1/C17H19NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,14H,7-10H2,1-2H3/t14-,17-/m1/s1

1668-86-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Narwedine

1.2 Other means of identification

Product number -
Other names rac-6-methoxy-10-methyl-galantham-1-en-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1668-86-6 SDS

1668-86-6Relevant articles and documents

A total synthesis of galanthamine involving de novo construction of the aromatic C-ring

Nugent, Jeremy,Matou?ová, Eli?ka,Banwell, Martin G.

, p. 3771 - 3778 (2015)

The tetracyclic alkaloid galanthamine is used clinically in a number of countries for the symptomatic treatment of mild to moderate forms of Alzheimer's disease, and this feature coupled with its novel molecular architecture has prompted an extensive focus on its synthesis. The present study reports a new and distinct synthesis of galanthamine wherein the AB-ring substructure and associated quaternary carbon centre are constructed by using a palladium-catalyzed intramolecular Alder-ene reaction. The product of this process is engaged in a Tsuji-Trost-type reaction to generate a semicyclic diene that participates in a normal-electron-demand Diels-Alder reaction to generate, after oxidation of the initially formed adduct, the aromatic C-ring of the target alkaloid. Modified Bischler-Napieralski chemistry is then deployed to construct the seven-membered D-ring and thereby furnishing narwedine, an established precursor to both (+)- and (-)-galanthamine. The first synthesis of the alkaloid galanthamine is reported in which the aromatic C-ring is assembled from non-aromatic precursors. This was accomplished by a Diels-Alder cycloaddition reaction. The diene used embodies the AB-ring system (and associated quaternary carbon centre) and was constructed by intramolecular Alder-ene and Tsuji-Trost-type chemistries. The D-ring was closed by a modified Bischler-Napieralski reaction.

Total synthesis of (±)-galanthamine from GABA through regioselective aryne insertion

Venkatesh, Telugu,Mainkar, Prathama S.,Chandrasekhar, Srivari

, p. 2192 - 2198 (2019/02/27)

The total synthesis of (±)-galanthamine is achieved in ~5% overall yield using a key regioselective aryne insertion reaction into a GABA (γ-amino butyric acid) derivative. The strategy presented involves only two sub-critical temperature reactions and less than five chromatographic purifications to achieve the synthesis of galanthamine.

An Eleven-Step Synthesis of Galanthamine from Commercially Available Materials

Nugent, Jeremy,Banwell, Martin G.

, p. 5862 - 5867 (2016/12/18)

Narwedine, an immediate precursor to the therapeutically valuable alkaloid (–)-galanthamine, has been synthesised by engaging an iodinated isovanillin derivative in an intermolecular Mitsunobu reaction with a 2-cyclohexen-1-ol derivative. The resulting aryl ether participated in an exceptionally efficient intramolecular Heck reaction to give a tetracyclic lactol after the hydrolysis of the primary cyclisation product. This last compound is an advanced intermediate associated with the Magnus synthesis of narwedine and could be elaborated to narwedine itself under reductive amination conditions. As a result, an eleven-step synthesis of galanthamine has been established.

Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors

Gallagher, Ryan,Chebib, Mary,Balle, Thomas,McLeod, Malcolm D.

, p. 1834 - 1841 (2015/12/26)

Alkaloids including galanthamine (1) and codeine (2) are reported to be positive allosteric modulators of nicotinic acetylcholine receptors (nAChRs), but the binding sites responsible for this activity are not known with certainty. Analogues of galanthamine (1), codeine (2), and morphine (3) with reactivity towards cysteine thiols were synthesized including conjugated enone derivatives of the three alkaloids 4-6 and two chloro-alkane derivatives of codeine 7 and 8. The stability of the enones was deemed sufficient for use in buffered aqueous solutions, and their reactivity towards thiols was assessed by determining the kinetics of reaction with a cysteine derivative. All three enone derivatives were of sufficient reactivity and stability to be used in covalent trapping, an extension of the substituted cysteine accessibility method, to elucidate the allosteric binding sites of galanthamine and codeine at nAChRs.

Stereoselective syntheses of galanthamine and its stereoisomers by complementary Luche and L-selectride reductions

Trinadhachari, Ganala Naga,Kamat, Anand Gopalkrishna,Raghu Babu, Korupolu,Sanasi, Paul Douglas,Prabahar, Koilpillai Joseph

, p. 117 - 124 (2014/02/14)

A diastereodivergent approach for the stereoselective syntheses of all four stereoisomers of galanthamine, (-)-galanthamine 1, (+)-galanthamine 2, (-)-epigalanthamine 3, and (+)-epigalanthamine 4, from (±)-narwedine 5 is reported. Thus (±)-narwedine 5 was resolved by dynamic kinetic resolution to obtain enantiomerically pure (-)-narwedine 6 and (+)-narwedine 7. Each enantiomerically pure isomer of narwedine was subjected to Luche and L-selectride reactions to obtain all four isomers of galanthamine. In these reactions, the (-)-galanthamine 1 and (+)-galanthamine 2 isomers were obtained with an enantiomeric purity of >99.5%, whereas (-)-epigalanthamine 3 and (+)-epigalanthamine 4 are obtained with a chiral purity of >97%. The axial hydride attack by the Luche reduction and the equatorial hydride attack by the L-selectride reduction on the cyclic enone system are explored in the stereoselective synthesis of the galanthamine isomers and thus it was demonstrated that the stereoselective synthesis involving the Luche and L-selectride reductions are complementary in yielding enantiomeric stereogenic centers from a prochiral carbonyl group on the cyclic enone system.

Commercial scale process of galanthamine hydrobromide involving Luche reduction: Galanthamine process involving regioselective 1,2-reduction of α,β-unsaturated ketone

Trinadhachari, Ganala Naga,Kamat, Anand Gopalkrishna,Prabahar, Koilpillai Joseph,Handa, Vijay Kumar,Srinu, Kukunuri Naga Venkata Satya,Babu, Korupolu Raghu,Sanasi, Paul Douglas

, p. 406 - 412 (2013/06/05)

Effect of lanthanide chloride in the Luche regioselective 1,2-reduction of 1-bromo-11-formyl-nornarwedine (5) was studied. Thus, 1-bromo-11-formyl- nornarwedine (5) is reduced with sodium borohydride in the presence of lanthanide chloride to yield 1-bromo-11-formyl-galanthamine isomers (6), which is a key intermediate for the commercial production of highly pure galanthamine hydrobromide (1), a modern drug against Alzheimer's disease.

Total synthesis of (±)-Galanthamine via a C3-selective stille coupling and IMDA cycloaddition cascade of 3,5-dibromo-2-pyrone

Chang, Jay Hyok,Kang, Ho-Ung,Jung, In-Hak,Cho, Cheon-Gyu

supporting information; experimental part, p. 2016 - 2018 (2010/06/21)

Figure presented A new efficient synthetic route to (±)-galanthamine was devised by using a tandem C3-selective Stille coupling-IMDA cascade of 3,5-dibromo-2-pyrone as a key strategy.

SYNTHESIS OF MORPHINE AND RELATED DERIVATIVES

-

Page/Page column 86-87, (2010/12/17)

The present invention relates to methods for the synthesis of galanthamine, morphine, intermediates, salts and derivatives thereof, wherein the starting compound is biphenyl.

Concise syntheses of (-)-galanthamine and (±)-codeine via intramolecular alkylation of a phenol derivative

Magnus, Philip,Sane, Neeraj,Fauber, Benjamin P.,Lynch, Vince

supporting information; experimental part, p. 16045 - 16047 (2010/02/16)

(Figure Presented). A new solution-processable fabrication protocol using a soluble tetrabenzoporphyrin (BP) precursor and bis(dimethylphenylsilylmethyl) [60]fullerene (SIMEF) created three-layered p-i-n photovoltaic devices, in which the i-layer possesses a well-defined bulk heterojunction structure in which columnar BP crystals grow vertically from the bottom p-layer. The device showed a power conversion efficiency of 5.2% (VOC = 0.75 V; JSC = 10.5 mA/cm2; FF = 0.65).

An improved process for the preparation of galantamine hydrobromide

-

Page/Page column 10; 11, (2009/01/24)

The present invention relates to an improved process for the preparation of [4aS,6R,8aS]-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol of Formula I

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