The crystal and molecular structure of (±)-octopamine hydrochloride

Paxton, Keith; Hamor, T.A.

doi:10.1107/s0567740877007912

Cited by 17 publications

(5 citation statements)

References 10 publications

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“…In molecule A the side chain is maximally extended and is approximately perpendicular to the phenol plane [torsion angles C(1)-C(7)-C(8)-N(1) = 179 and C(2)-C(1)-C(7)-C(8) = 74 ° ]. The distance of the amino N from the center of the benzene ring is 5.24 A and the height of this N atom from the benzene plane is 1.57 A. Neosynephrine, norsynephrine (Paxton & Hamor, 1977) and most of the sympathomimetic amines studied so far adopt a similar conformation and this appears to be a preferred conformation necessary for activity at the receptor site (Duax, 1978;Carlstr6m, Bergin & Falkenberg, 1973). The amino group is gauche to the hydroxyl group at the side chain and this again is consistent with other studies not only in the solid state but also in liquid and gas phases (Portoghese, 1967;Penn & Curl, 1971).…”

Section: Discussionmentioning

confidence: 99%

Structure of synephrine monohydrogenphosphate monohydrate

Dattagupta¹,

Meyer²,

Mukhopadhyay³

1982

Acta Crystallogr Sect B

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Abstract2C9H14NO~-.HPOE-.H2 O, M r --450.4, monoclinic, P21/n, a = 12.108(4), b = 8.402(2), c = 21.549 (6)A, fl = 99.67 (3) °, Z = 4, D e = 1.384 Mg m -3, Cu Ka radiation, 2 = 1.54184 A,/z(Cu Ka) = 1.588 mm -I, V--2161.1A 3, F(000) = 960. The structure was solved by direct methods and refined by full-matrix least-squares calculations to a final R = 0.056 for 2562 uniquely observed diffractometer data with I > 2tr(I). The two molecules in the asymmetric unit exhibit different conformations, one of them being closely similar to other sympathomimetic amines including neo-and norsynephrine. The crystal structure is stabilized by a three-dimensional network of H bonds with p-hydroxyl and amino groups of the synephrine cations strongly bonded to O atoms of the phosphate anion, indicating a putative environment of these drug molecules at their receptor and storage sites in biological systems.

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Section: Discussionmentioning

confidence: 99%

Structure of synephrine monohydrogenphosphate monohydrate

Dattagupta¹,

Meyer²,

Mukhopadhyay³

1982

Acta Crystallogr Sect B

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“…Final fractional coordinates with mean isotropic temperature factors are in Table 1. (+)-NORPHENYLEPHRINE HYDROCHLORIDE 1973), (-)-adrenaline (Andersen, 1975a), (-)-noradrenaline hydrochloride (Carlstr6m & Bergin, 1967), (-)-noradrenaline (Andersen, 1975b), adrenalone hydrochloride monohydrate (Bergin, 1971), dopamine hydrochlori.de (Bergin & CarlstrOm, 1968), (-)-phenylephrine (Andersen, 1976), (+)-isoprenaline sulfate dihydrate (Mathew & Palenik, 1971), (+)-isoprenaline (Parvez, 1977), (+)-salbutamol (Beale & Stephenson, 1972), (+)-p-octopamine hydrochloride (Paxton & Hamor, 1977) and (+)-o-octopamine hydrochloride (Makriyannis, Anderson, Dipiro, Kostiner & Hite, 1979). In the crystal structure of (1).HCI the cation adopts the gauche conformation shown in Fig.…”

Section: Table 2 Molecular Dimensions (~ °)mentioning

confidence: 99%

“…Whether a gauche or anti conformation about the C(7)-C(8) bond is adopted in the solid state is clearly under crystal packing control. In o-octopamine hydrochloride (Makriyannis et al, 1979) with the anti conformation, there is an intramolecular OH...O hydrogen bond, and the terminal -N+H3 group is hydrogen bonded to two CI-ions and a side-chain OH of a related ion; in p-octopamine hydrochloride (Paxton & Hamor, 1977) the same type of inter-ion hydrogen bonding is observed. The hydrogen bonding in (1).HCI is shown in Fig.…”

Section: Table 2 Molecular Dimensions (~ °)mentioning

confidence: 99%

(±)-Norphenylephrine hydrochloride (m-octopamine hydrochloride), C8H12NO2+.Cl−

Ferguson¹,

Parvez²,

Ruhl³

et al. 1984

Acta Crystallogr C

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“…The structure of L-phenylephrine (free-base form) was reported earlier (Andersen, 1976). It was thought worthwhile to look at the structure of the therapeutically prescribed form, L-phenylephrine hydrochloride, so that one can compare the structural and conformational features with those of the free base L-phenylephrine, synephrine (Dattagupta, Meyer & Mukhopadhyay, 1982), norsynephrine (Paxton & Hamor, 1977), and of other sympathomimetic drugs most of which are found to assume a preferred conformation in the crystalline state (Carlstr6m, Bergin & Falkenberg, 1973). A preliminary account of this structure was reported earlier (Bhaduri & Saha, 1975), and the complete solution of the structure and its refined parameters are presented here.…”

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confidence: 99%