A monoclinic polymorph of venlafaxine hydrochloride

Sivalakshmidevi, A.; Vyas, K.; Rao, S. Mahender; Reddy, G. Om

doi:10.1107/s160053680201588x

Cited by 14 publications

(11 citation statements)

References 6 publications

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“…Desvenlafaxine is asynthetic formofthe major active metabolite of venlafaxine and is being investigated as the first non-hormonal based treatment for menopause. It is aracemic mixture and is reported to exist in four crystalline polymorphs [2].Furthermore the crystal structure of venlafaxine hydrochloride [3], am onoclinic polymorph of venlafaxine hydrochloride [4],venlafaxine itself [5], desvenlafaxine succinate monohydrate [6] and two polytypes of desvenlafaxine succinate monohydrate [7]h aveb eenr eported. Thec rystal structure of at ernary complex,4 -(2-pyridyl)pyridinium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid (1/1/1), is apparent in the literature [8], and an orthorhombic-to-monoclinic temperature-dependent phase transition of hexa-methylenetetraminium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid monohydrate in the solid state has been described [9].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of desvenlafaxinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid monohydrate, C30H35N5O15

Kaur

Yathirajan

Byrappa

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialDesvenlafaxine succinatewas obtained as agift sample from R. L. Fine Chem,B engaluru,I ndia. As olution of desvenlafaxine succinate in water was treated with ammonium hydroxide solution till apH>7was reached upon which awhite precipitate of desvenlafaxine was obtained. The precipitate was filtered and driedinopen airovernight.Itwas used for the preparation of the dinitrobenzoate salt without further purification. Desvenlafaxine (200 mg, 0.76 mmol) and 3,5-dinitrobenzoic acid (161 mg,0.76 mmol) were dissolved in hot methanol and stirred at 333 Kfor 30 minutes. The resulting solution was allowed to cool slowly to room temperature. The salt obtained was filtered and dried in a vacuum desiccator over phosphorous pentoxide. The resulting compound was recrystallized from acetonitrile by slow evaporation. Experimental detailsCarbon-bound Hatomswere placed in calculated positions (C-H 0.95 Å, C-H 0.99 Åfor methylene groups and C-H 1.00 Åfor methine groups) and were included in the refinement in the riding model approximation, with U iso (H) setto1.2U eq (C). The Hatoms of the methyl groups were allowed to rotate with afixed angle around the C-C bond to best fit the experimental electron density (HFIX 137 [7]h aveb eenr eported. Thec rystal structure of at ernary complex,4 -(2-pyridyl)pyridinium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid (1/1/1), is apparent in the literature [8], and an orthorhombic-to-monoclinic temperature-dependent phase transition of hexa-methylenetetraminium-3,5-dinitrobenzoate-3,5-dinitrobenzoic acid monohydrate in the solid state has been described [9]. In the crystal, amolecule of water is present next to onea dditional molecule of the -n on-dissociated -c arboxylic acid. While the least-squares planes defined by the atomsofthe nitro groups of the deprotonated carboxylic acid enclose angles of 5.8(2)°and 9.8(2)°with the plane defined by the carbon atomsof thearomaticsystemtheyare bonded to,t he least-squares plane defined by theatoms of thecarboxylate groupintersectwiththe aromat's planeatanangle of 13.88(14)°.T he respective values fort he co-crystallized carboxylic acid are found at 4.9(2)°and 7.25(16)°for thenitro groups and 11.12(16)°for the least-squares plane defined by the non-hydrogen atomsofthe carboxylic acid group on the one hand and the plane defined by the carbon atoms of the aromatic system they are bonded to on the other hand. According to apuckering analysis, the saturated six-membered ring adopts a 4 C 1 conformation ( C24 C C21 ) [10,11]. In the crystal, hydrogen bonds of the N-H×××Oaswell as the O-H×××Otype areob-

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Section: Discussionmentioning

confidence: 99%

Crystal structure of desvenlafaxinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid monohydrate, C30H35N5O15

Kaur

Yathirajan

Byrappa

et al. 2014

Zeitschrift Für Kristallographie - New Crystal Structures

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“…For background information, see: Venu et al (2008); Tessler & Goldberg (2004);Van Eupen et al (2008); Yardley et al (1990); Banjeree et al (2005); Vega et al (2000); Sivalakshmidevi et al (2002); Roy et al (2007). For ring-puckering calculations, see: Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

“…This intramolecular hydrogen bond is absent in the Venlafaxine cation, probably due to the presence of an extra hydrogen atom at N1. The mean value of the torsion angle C8-C7-C14-N1 on six cation molecules is 138 (7)° (refcodes KIDGUZ, VAWQAM, WOBMUV, WOBMUV01 and two molecules in WOBMUV02) (Yardley et al, 1990, Banjeree et al, 2005, Vega et al, 2000, Sivalakshmidevi et al, 2002, Roy et al, 2007, featuring the open conformation for cations. However, the crystal structure introduced here is the first case where a Venlafaxine cation is in a closed conformation.…”

Section: S1 Commentmentioning

confidence: 99%

Venlafaxine besylate monohydrate

Corvalán

Vega

2013

Acta Cryst E

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The title compound {systematic name: [2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]dimethylazanium benzenesulfonate monohydrate}, C17H28NO2 +·C6H5O3S−·H2O, is a besylate salt hydrate of the antidepressant drug venlafaxine. In the crystal, besylate anions and water molecules self-assemble, forming hydrogen-bonded dimers linked around inversion centers, with graph set R 4 4(6). The crystal packing features a chain of alternate dimers and venlafaxine cations in the b-axis direction with the components linked by O—H⋯O hydrogen bonds and C—H⋯O and C—H⋯π interactions. This is the first example of a venlafaxine cation with a closed conformation, as it features an intramolecular N—H⋯O interaction involving the protonated N atom.

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“…For the pharmacological importance of Desvenlafaxine {systematic name: 4-[2-dimethylamino-1-(1-hydroxycyclohexyl)ethyl]phenol}, see: Deecher et al (2006). For related structures, see: Dayananda et al (2012); Duggirala et al (2009); Hadfield et al (2004); Mungkornasawakul et al (2009); Sivalakshmidevi et al (2002); Sun et al (2006); Tessler & Goldberg (2004); Vega et al (2000); Venu et al (2008); Zhang et al (2006). For puckering parameters, see: Cremer & Pople (1975).…”

Section: Related Literaturementioning

confidence: 99%

“…It is a racemic mixture and is reported to exist in four crystalline polymorphs (Hadfield et al, 2004). The crystal structure of venlafaxine hydrochloride (Vega et al, 2000), a monoclinic polymorph of venlafaxine hydrochloride (Sivalakshmidevi et al, 2002), venlafaxine (Tessler & Goldberg, 2004), desvenlafaxine succinate monohydrate (Venu et al, 2008) and two polytypes of desvenlafaxine succinate monohydrate (Duggirala et al, 2009) have been reported. Some of the ethyl acetate solvate structures reported are:…”

Section: S1 Commentmentioning

confidence: 99%

Desvenlafaxinium chloranilate ethyl acetate solvate

et al. 2013

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Key indicators: single-crystal X-ray study; T = 123 K; mean (C-C) = 0.004 Å; disorder in solvent or counterion; R factor = 0.057; wR factor = 0.158; data-toparameter ratio = 24.7.In the cation of the title compound, C 16 H 26 NO 2 + ÁC 6 HCl 2 O 4 À Á-C 4 H 8 O 2 , the 1-hydroxy-cyclohexyl ring adopts a slightly distorted chair conformation. The dihedral angle between the mean planes of the 1-hydroxycyclohexyl and 4-hydroxyphenyl rings is 84.0 (8) . In the anion, the hydroxyl H atom is twisted slightly out of the ring plane with a C-C-O-H torsion angle of À171.9 . Disorder was modeled for the methyl group of the acetate group in the solvate with an occupancy ratio of 0.583 (15)

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A monoclinic polymorph of venlafaxine hydrochloride

Cited by 14 publications

References 6 publications

Crystal structure of desvenlafaxinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid monohydrate, C30H35N5O15

Crystal structure of desvenlafaxinium 3,5-dinitrobenzoate 3,5-dinitrobenzoic acid monohydrate, C30H35N5O15

Venlafaxine besylate monohydrate

Desvenlafaxinium chloranilate ethyl acetate solvate

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