13425-06-4

Basic information

• Product Name: CSH 068
• Synonyms: CSH 068;Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-((4-methoxyphenyl)methyl)-2-methyl-
• CAS NO: 13425-06-4
• Molecular Formula: C20H25NO3
• Molecular Weight: 327.4174
• Mol File: 13425-06-4.mol

Chemical Properties

• Boiling Point: 445.7°Cat760mmHg
• Flash Point: 126.9°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 3.87E-08mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: CSH 068(CAS DataBase Reference)
• NIST Chemistry Reference: CSH 068(13425-06-4)
• EPA Substance Registry System: CSH 068(13425-06-4)

Safety Data

• Hazardous Substances Data: 13425-06-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H25NO3/c1-21-10-9-15-12-19(23-3)20(24-4)13-17(15)18(21)11-14-5-7-16(22-2)8-6-14/h5-8,12-13,18H,9-11H2,1-4H3

Upstream product

• 518-34-3 Tetrandrin 
• 5096-71-9 (+)-O-methylthalicberine 
• 477-57-6 (+)-isotetrandrine 
• 50-00-0 formaldehyd 
• 186581-53-3 diazomethane 
• 87183-77-5 (+)-O,O-Dimethylvanuatine 
• 182305-80-2 {(S)-1-[(S)-6,7-Dimethoxy-1-(4-methoxy-benzyl)-3,4-dihydro-1H-isoquinolin-2-yl]-pyrrolidin-2-yl}-methanol 
• 3611-33-4 O,O-Dimethylcoclaurine 
• 182305-82-4 (9R,13S)-2,3-Dimethoxy-6,9,13,15,16,17-hexahydro-7H,12H-11-oxa-8,14-diaza-cyclopenta[a]phenanthrene 
• 123190-12-5 2-(2-bromoethyl)-4,5-(dimethoxy)benzaldehyde 
• 93780-79-1 (+)-thaliphylline 
• 38769-92-5 4-methoxybenzylmagnesium chloride 
• 51714-24-0 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline-1-carbonitrile 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 7630-50-4 N,O-dimethyl-N-norarmepavine methyliodide 

Relevant articles and documents

Effect of isoquinoline alkaloids of different structural types on antiplatelet aggregation in vitro

Forty-one isoquinoline alkaloids were tested for antiplatelet aggregation effects. Among them, (-)-discretamine (6), protopine (7), ochotensimine (18), O-methylarmepavinemethine (23), lindoldhamine (25), isotetrandrine (26), thalicarpine (27), papaverine (28), and D-(+)-N-norarmepavine (32) exhibited significant inhibitory activity towards adenosine 5′-diphosphate (ADP)-, arachidonic acid (AA)-, collagen-, and/or platelet-activating factor (PAF)-induced platelet aggregation. The results are discussed on the basis of structure-activity relationships. Georg Thieme Verlag KG Stuttgart.

Dehatrine, an antimalarial bisbenzylisoquinoline alkaloid from the Indonesian medicinal plant Beilschmiedia madang, isolated as a mixture of two rotational isomers

Through bioassay-guided separations of the chemical constituents of the Indonesian medicinal plant Beilschmiedia madang BL. A bisbenzylisoquinoline alkaloid was obtained as the major antimalarial principle. The physicochemical properties of the alkaloid were consistent with the proposed structure of dehatrine (1). However, the alkaloid isolated by us was shown to be a mixture of two rotational isomers. The X-ray crystallographic analysis of 1 has shown that two rotamers are incorporated in a single crystal 1:1 ratio. The complex NMR spectrum of 1 has also been defined as a mixture of two rotamers by extensive use of 2D (COSY and COLOC) techniques. Dehatrine (1) has been shown to significantly inhibit the growth of cultured Plasmodium falciparum K1 strain (chloroquine resistant) with similar activity to quinine.

Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C-C-Bond Metathesis

A light-induced C-C-σ-bond metathesis was achieved through transition-metal-free activation of an unstrained C(sp3)-C(sp3)-σ-bond in 1-benzyl-1,2,3,4-tetrahydroisoquinolines. A photoredox-mediated single-electron oxidation of these precursor amines yield radical cations which undergo a homolytic cleavage of a C(sp3)-C(sp3)-σ-bond rather than the well-known α-C-H-scission. The resulting carbon-centered radicals are used in the ipso-substitution of (hetero)aromatic nitriles proceeding through another single-electron transfer-mediated C-C-bond cleavage and formation.

Enantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme

N-Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers o

Synthesis of (+)-O-methylthalibrine by employing a stereocontrolled Bischler-Napieralski reaction and an electrochemically generated diaryl ether

An efficient electrochemical four-step route was developed for the preparation of diaryl ether derivatives by using halogenation and dehalogenation processes in addition to electrochemical phenolic oxidation and reduction reactions. The synthesis of (+)-O

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.

A new benzylisoquinoline alkaloid from Argemone mexicana

A new benzylisoquinoline alkaloid, argemexirine, together with two known protoberberine alkaloids, dl-tetrahydrocoptisine and dihydrocoptisine, have been isolated from the methanolic extract of the whole plant of Argemone mexicana L. The compounds were identified by spectral and chemical evidence. This is the first report of these alkaloids in this plant species.

Method and health food for preventing and/or alleviating psychiatric disorder, and/or for effectuating sedation

A method for preventing and/or alleviating a psychiatric disorder, and/or effectuating sedation, comprising administering a benzylisoquinoline derivative represented by General Formula (I): wherein R1, R2, R3 and X each re

A novel straightforward synthesis of enantiopure tetrahydroisoquinoline alkaloids

A novel, direct, and high-yielding stereoselective method for enantiopure 1-substituted tetrahydroisoquinolines (THIQ) is described. The successful approach, which creates the stereocenter during the formation of the THIQ nucleus is based on (i) formation of chiral 2,3-substituted perhydro-1,3-benzoxazines derived from (-)-8-aminomenthol, (ii) diastereoselective intramolecular ring opening of the N,O-acetal moiety by an arylmetal generated from the substituent at the nitrogen atom in the perhydrobenzoxazine ring, and (iii) removal of the chiral auxiliary appendage. The starting perhydrobenzoxazines are easily prepared from (-)-8-aminomenthol and two different aldehydes, and the intramolecular opening is stereospecific, leading to a single stereoisomer. The method allows the preparation of a wide variety of enantiopure 1-substituted THIQ, with different substituents at C-1, by changing the nature of the starting aldehydes.

Syntheses of the seco benzyltetrahydroisoquinoline alkaloids polysignine and methoxypolysignine

The structures previously assigned to the seco benzyltetrahydroisoquinoline alkaloids polysignine (1) and methoxypolysignine (2) have been confirmed by total syntheses in which the key step involved cleavage of the C 1-N bonds in the corresponding N-methylbenzyltetrahydroisoquinolines. CSIRO 2000.