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PubMed2003

Dose-response related efficacy in orthostatic hypotension of a fixed combination of D-camphor and an extract from fresh crataegus berries and the contribution of the single components.

Independent, double-blinded, randomized, placebo-controlled studies using sublingual/oral administration of D-camphor, an extract from fresh crataegus berries, and a combination of the two (CCC) yielded the following results: Both the D-camphor and the extract from fresh crataegus berries, the components of CCC, contribute to the pressoric effects of the combination. The underlying hemodynamic mechanisms can be attributed to an increase in total peripheral resistance induced by an increased tone of the arterioles with both components and the effect of crataegus is intensified by an additional direct positive action on cardiac performance. Conceivably, the D-camphor component is the main factor in inducing the rapid initial effect, whereas the extract from fresh crataegus berries adds a long-lasting effect. For CCC, a dose-dependent increase in supine blood pressure and prevention of orthostatic fall in blood pressure following tilt table-induced orthostasis in patients with orthostatic dysregulation was demonstrated as well. The effect revealed a very rapid onset of action within 1 min following administration, confirming the traditional use in emergency situations such as orthostatic (pre)syncope. Thus, these studies show that CCC, depending on the pressoric activity of its two mono-components, exerts a significant effect that counteracts an orthostatic fall in blood pressure and thereby provides a rationale for its application that reemphasizes the decades-long usefulness of this phyto-combination.

Administration, Oral↗
PubMed1999

Release of benzimidazole and benzylidene camphor from topical sunscreen formulations.

Absorption of two ultraviolet (UV) filters was evaluated through a lipophilic synthetic membrane (Folioxane) and excised hairless rat skin using a flow-through diffusion cell. Folioxane membrane is an artificial skin used in the treatment of third-degree burns. Diffusion tests were performed with aqueous solutions and galenic formulations (one water-in-oil [W/O] emulsion and two oily gels). Analyses were achieved with high-performance liquid chromatography (HPLC) with UV detection at 295 nm. Diffusion kinetics of 17 beta estradiol, a reference compound, through rat skin, human skin, and Folioxane membrane were performed to validate the in vitro model. Phenylbenzimidazole and methylbenzylidene camphor in aqueous solutions were diffused at a regular rate through the Folioxane film. The release of phenylbenzimidazole was very slow, whereas the release of benzylidene camphor was more pronounced: a decrease of the quantity was observed in the donor compartment (30% at 6 hr and 93% after 72 hr). A significant flow of benzylidene camphor was also measured through excised skin of rat in the first 3 hr. The skin absorption was 38% over 72 hr. The W/O emulsion had low penetration of UV filter: 20% of the initial amount for Folioxane membrane and 0.4% for rat skin. In contrast, the penetration of two oily gels was identical: 28% on Folioxane membrane and 0.6% on rat skin. This study demonstrates the transcutaneous diffusion of two important classes of sunscreens through a lipophilic Folioxane membrane and through excised hairless rat skin. From the results, Folioxane membrane appears to be an alternative model for studying diffusion of topical molecules and as a tool for guiding formulation choices.

Administration, Topical↗
PubMed1982

The pressure dependence of the spin equilibrium in camphor-bound ferric cytochrome P-450.

The spin equilibrium of camphor-bound ferric cytochrome P-450 has been measured between 1-1000 bar (10(5)-10(8) Pa). Increasing pressure shifts the absorption spectrum from the high-spin form at 392 nm to the low-spin form at 417 nm. The molar volume change for the spin states delta V = -RT delta ln Ke/ delta P and the equilibrium coefficient Ke = [high spin]/[low spin] depend on the solvent conditions. At pH 5.6 the equilibrium coefficient at 1 bar, K1 = 0.5 and delta V = 312 cm3/mol. A sample with 10 mM KCl at pH 7 has K1 = 7.0 amd delta V = 52 cm3/mol. Solvent changes producing a larger K1 also result in a larger delta V which ranged over 16-74 cm3/mol. The correlation can be approximated as delta V = 36 + 18 log K1, which implies that there is a pressure, 3000 bar, for camphor-bound ferric cytochrome P-450 at 4 degrees C, at which the changes in delta V are compensated by the other thermodynamic parameters leaving Ke independent of the solvent conditions. Although the protein is not stable about 1000 bar for most sample conditions, the extrapolated log Ke versus pressure curves for all sample conditions intersect near 3000 bar. Camphor-bound cytochrome P-450 appears to be a rather flexible protein, having a low denaturing pressure, a large volume change, and a high sensitivity to the protein environment.

Camphor↗
PubMed2004

Dermal absorption of camphor, menthol, and methyl salicylate in humans.

Camphor, menthol, and methyl salicylate occur in numerous over-the-counter products. Although extensively used, there have been no estimates of human exposure following administration via dermal application. Furthermore, there is little information about the pharmacokinetics of those compounds. The authors report the plasma concentrations of the intact compounds as a function of dose following dermal patch application. Three groups of 8 subjects (4 male, 4 female) applied a different number of commercial patches (2, 4, or 8) to the skin for 8 hours. Plasma samples were assayed using sensitive and selective gas-chromatographic methods. For the 8-patch group, the average maximum plasma concentrations (Cmax +/- SD) were 41.0 +/- 5.8 ng/mL, 31.9 +/- 8.8 ng/mL, and 29.5 +/- 10.5 ng/mL for camphor, menthol, and methyl salicylate, respectively. The corresponding values for the 4-patch group were 26.8 +/- 7.2 ng/mL, 19.0 +/- 5.4 ng/mL, and 16.8 +/- 6.8 ng/mL. The harmonic mean terminal half-lives were 5.6 +/- 1.3 hours, 4.7 +/- 1.6 hours, and 3.0 +/- 1.2 hours for camphor, menthol, and methyl salicylate, respectively. The 2-patch group had measurable but low plasma concentrations of each compound. Low-dose dermal application for an extended time results in low plasma concentrations of all 3 compounds. Four and 8 patches, when applied for 8 hours, gave measurable and nearly proportional plasma concentrations. Although unable to determine the absolute dermal bioavailability of these compounds, there appears to be relatively low systemic exposure to these potentially toxic compounds, even when an unrealistically large number of patches are applied for an unusually long time.

Administration, Topical↗
PubMed1991

Effects of l-menthol and dl-camphor on the penetration and hydrolysis of methyl salicylate in hairless mouse skin.

Plasters containing methyl salicylate with and without l-menthol and dl-camphor were prepared and topically applied on hairless mouse skin to investigate the effects of l-menthol and dl-camphor on the skin penetration and hydrolysis of methyl salicylate in the skin. The in vitro hydrolysis of methyl salicylate was also investigated using the skin homogenate. It was found that l-menthol with dl-camphor enhanced the skin penetration of methyl salicylate, and they inhibited both the in vivo and in vitro hydrolysis of methyl salicylate to salicylic acid.

Administration, Topical↗
PubMed2004

Total degradation of pentachloroethane by an engineered Alcaligenes strain expressing a modified camphor monooxygenase and a hybrid dioxygenase.

We engineered biphenyl-degrading Alcaligenes sp. strain KF711 for total degradation of pentachloroethane (PCA), which expresses a modified camphor monooxygenase and a hybrid dioxygenase consisting of TodC1 (a large subunit of toluene dioxygenase of Pseudomonas putida F1) and BphA2-BphA3-pbhA4 (a small subunit, ferredoxin and ferredoxin reductase of biphenyl dioxygenase, respectively, in strain KF707). Modified camphor monooxygenase genes (camCAB) were supplied as a plasmid and the todC1 gene was integrated within the chromosomal bph gene cluster by a single crossover recombination. The resultant strain KF711S-3cam dechlorinated PCA to trichloroethene by the action of the modified camphor monooxygenase under anaerobic conditions. The same strain subsequently degraded trichloroethene formed oxidatively by the action of the Tol-Bph hybrid dioxygenase under aerobic conditions. Thus sequential anaerobic and aerobic treatments of the KF711S-3cam resting cells resulted in efficient and total degradation of PCA.

Alcaligenes↗
PubMedDate not supplied

The effects of camphor, eucalyptus and menthol vapour on nasal resistance to airflow and nasal sensation.

The effects of five minutes exposure to camphor, eucalyptus or menthol vapour on nasal resistance to airflow and nasal sensation of airflow were compared with the effects of exercise on the nose. Inhalation of camphor, eucalyptus or menthol had no effect on nasal resistance to airflow but the majority of subjects reported a cold sensation in the nose with the sensation of improved airflow. Exercise caused a decrease in nasal resistance but did not induce any nasal sensation of cold or improved airflow. The results indicate that camphor, eucalyptus and menthol stimulate cold receptors in the nose. The clinical significance of nasal sensation of airflow is discussed.

Adult↗
PubMed2001

Laboratory evaluation of the insecticidal activity of camphor on the development of Oestrus ovis larvae.

The essential oil of E. globulus leaves or camphor against the maturation of Oestrus ovis larvae was evaluated at the laboratory conditions. Camphor at concentrations 1:0 and 1.1 showed 100% mortality rate. At concentrations of 1:2-1:6 the mortality rate ranged between 45-98%. On the other hand, 38 or 27.5% of the developed pupae emerged to adults but only 36.8% of them were fertile. Camphor is safely used in Medicine. So, it is recommended in controlling the zoonotic myiasis producer, O. ovis.

Animals↗
PubMed2004

[Synthesis and luminescence properties of europium (III ) complexes with camphoric acid and 1,10-phenanthroline].

The complexes of europium(II) with camphoric acid and 1,10-phenanthroline have been synthesized and characterized by elemental analysis, (1)H NMR, IR and FT-Raman. The compositions of the complexes have been confirmed to be Eu2 (CA)3.(2)H2O and Eu2 (CA)3 (phen)2 (CA: camphoric acid, phen: 1, 10-phenanthroline). In addition, the camphoric acid and 1, 10-phenanthrolinemixed coordination compounds of Eu3+ -La3+ have been synthesized. Three-dimensional fluorescence spectra showed that the optimum excitation wavelength was 310 nm, and the strongest emission wavelength was 612 nm. When 310 nm light was used as an excitation wavelength, the seven bands due to (5)D0 - (7) F0 (579 nm), (5)D0 - (7)F1 (594 nm), (5)D0 - (7)F2 (612 and 620 nm), (5)D0 - (7)F3 (650 nm) and (5)D0 - (7)F4 (689 and 697 nm) were observed between 550-700 nm, in which (5)D0 - (7)F2 transitions contain two lines (612 and 620 nm), and (5)D0 - (7)F4 transitions also contain two lines (689 and 697 nm). The excitation spectra showed that excitation band was from 240 to 340 nm, and the maximum was at about 310 nm. The fluorescence studies on all of samples showed that the fluorescence intensities of europium ions were sensitized by lanthanum ions, but the peak position of their emission band did not shift obviously.

Camphor↗
PubMed2005

[Historical study of the moth repellent, "Fujisawa Camphor" (7) - selling price and packaging.].

The selling price of "Fujisawa Camphor" has increased 1,000-fold in the 100 years since it first went on sale. This 1,000-fold increase is not high at all. The price of "Fujisawa Camphor" was not low in the 1980s, one of grounds for setting the price was the damage caused by moths to expensive Japanese clothes and curios. For packaging in the Edo era, being wrapped in paper was the mainstream form, but modern-age packaging shifted to a cardboard box. As for "Fujisawa Camphor", a beautiful design was created for the cardboard.

Animals↗
PubMed1984

Camphor toxicity: development of a triage strategy.

Camphor remains in over 950 products listed in Poisindex. To provide triage guidelines for gastric decontamination and referral, we reviewed all camphor ingestions estimated to be 2 mg/kg or greater reported to U. VA (1980-83) and to M.C.V. (1982-83). Seventy-three patients (90%) remained asymptomatic, 3 (4%) developed minor symptoms, and 5 (6%), all ingesting over 59 mg/kg, developed major symptoms. There were no deaths. (table; see text) A literature review of 63 evaluable cases revealed 6 deaths; the mean fatal dose was 199 mg/kg (range 64-570, median 113). Based on these data, we manage asymptomatic patients ingesting camphor at less than 10 mg/kg by observation only 10-30 mg/kg at home with 1 g/kg activated charcoal or emesis, and over 30 mg/kg by gastric decontamination plus referral.

Camphor↗
PubMed1996

[dl-Camphor Reference Standard (Control 951) of the National Institute of Health Sciences].

The raw material of dl-camphor was examined for the preparation of the "dl-Camphor Reference Standard". Analytical data obtained are as follows: ultraviolet spectrum, lambda max = 290 nm; infrared spectrum, the same as that of the present JP Camphor Reference Standard; melting point, 179.6 degrees C; purity test by gas-chromatography (GC), three kinds of impurities were detected; assay by GC, 99.0%. Based on the above results, the candidate raw material was authorized as the JP Reference Standard (Control 951).

Camphor↗
PubMed1997

Reproductive toxicity studies of D-camphor in rats and rabbits.

The embryotoxicity of D-Camphor (CAS 76-22-2), orally employed for the treatment of hypotonic circulatory dysregulations, was investigated in rats and rabbits. D-Camphor elicited no evidence of teratogenicity when administered orally during the fetal period of organogenesis to pregnant rats at doses up to 1000 mg/kg b.w./day, and to pregnant rabbits at doses up to 681 mg/kg b.w./day. The no-observed-effect level for the fetal organism for the rat was above 1000 mg/kg b.w., and for the rabbit above 681 mg/kg b.w. In rat dams a dose-dependent reduction in food intake and salivation was noted from 464 mg/kg b.w./p.o. onwards. The high dose of 1000 mg/kg b.w./d p.o. resulted in fairly pronounced signs of toxicity such as clonic convulsion, pilo-erection, reduced motility and reduced body weight gain. In rabbit dams the high dose level of 681 mg/kg b.w./d p.o. resulted in reduced body weight gain and food consumption. No increased incidence in variations, retardations or malformations were observed at any of the treated dose levels not even at the highest tested dose level (rat: 1000 mg/kg b.w./d p.o.; rabbit: 681 mg/kg b.w./d p.o.). The daily maximum human therapeutic camphor dose is approximately 1.43 mg/kg b.w. Hence, under the present test conditions the therapeutic ratio is above 450 for the endpoint embryotoxicity reflecting a wide margin of safety.

Animals↗
PubMed2007

Alternative synthetic route to chiral N-substituted camphor-derived beta-amino alcohols.

An alternative route from (1R)-(+)-camphor to chiral N-substituted camphor-derived beta-amino alcohol (4b-e) consists of four steps with a total yield of 28%. N-Alkylation of camphor-derived beta-amino alcohol (4a) involves condensation and hydride reduction in one pot without isolation of intermediates. Condensation of 4a with aldehydes or ketones generates a mixture of 1,3-oxazolidines (6) and imino-alcohols (7), which are reduced to 4b-e by NaBH(4).

Journal Article↗
PubMed1997

Central to Axial Transfer of Chirality in Menthone or Camphor-Derived 2,2'-Biphenols.

A study aimed at defining a molecular arrangement where a chiral fragment derived from menthone or camphor transfers its central chirality to a 2,2'-biphenol residue, inducing an axial chirality, is reported. The menthol or isoborneol groups are attached at the two benzylic positions at 3,3' in order to maximize efficiency in practical applications. A reliable and high-yielding procedure for the synthesis of such C(2)-symmetric molecules substituted at the 3,3'-positions has been developed. The procedure entails Mannich condensation with paraformaldehyde and morpholine, protection of the hydroxylic functions, chlorination, metalation, and addition to (-)-menthone and (+)-camphor. The use of samarium diiodide is essential in the latter step for optimum selectivity and efficiency. The tetrols exhibit intramolecular hydrogen bonding between phenolic and alcoholic hydroxy functions within each monomeric unity, so that they retain their rotational freedom. NOEDS and COSY experiments show that the tetrols are present in more than one rotamer. The tetrols react with tetrachlorosilane to afford siloxanes as pure diastereoisomers, showing that the metal is able to induce preferential helicity at the biphenyl residue; i.e., the central chirality of menthol or isoborneol auxiliary is totally transfered to the axial chirality of the biphenyl. The configurations could be determined by NOEDS and heterocorrelated HMQC experiments. Remarkably, while the menthol derivative induces total M helicity, the camphor induces complementary P helicity. These results suggest that these tetrols may be useful as ligands in catalysts for asymmetric synthesis.

Journal Article↗
PubMed1999

1H and (13)C NMR and Molecular Dynamics Study of Chiral Recognition of Camphor Enantiomers by alpha-Cyclodextrin.

1H and (13)C NMR spectra of the complexes of camphor enantiomers with alpha-cyclodextrin in D(2)O manifest splittings due to chiral recognition. The complexes were found to be of 1:2 guest-to-host stoichiometry. Free energies of the complex formation obtained from (1)H NMR titration data are equal to -7.95 +/- 0.09 kcal mol(-)(1) for the complex with (1S,4S)- and -7.61 +/- 0.06 kcal mol(-)(1) for that with (1R,4R)-enantiomer. Thus, the free energy difference between the complexes is equal to 0.34 +/- 0.11 kcal mol(-)(1), with the complex involving the (1S,4S)-camphor more stable. A strong positive cooperativity of the guests binding has been found. In agreement with experimental results, molecular dynamics simulations yielded greater stability of the complex with (1S,4S)-camphor. However, they reproduced only qualitatively the experimental trend since the corresponding difference in average energies obtained from molecular dynamic simulations carried out in a water solution is equal to 5 kcal/mol with the CVFF force field.

Journal Article↗
PubMed2002

Eucalyptus globulus (camphor oil) in the treatment of human demodicidosis.

Demodex folliculorum (Follicular or Demodicid mite) is a zoonotic obligatory parasite with clinical manifestations range from normal infestation to complicated ones. Treatment of human facial demodicidosis with freshly prepared camphor oil with or without glycerol dilutions gave complete cure with concentrations of 100%, 75%. and 50%. Incomplete cure but marked drop in infestation density was achieved with diluted camphor oil at concentrations of 25-20%. Camphor oil application proved to be safe with no side effects.

Adolescent↗
PubMed1994

Effects of monovalent cations on cytochrome P-450 camphor. Evidence for preferential binding of potassium.

Binding of monovalent cations of increasing ionic radius to ferric cytochrome P-450cam was measured. Potassium has the highest affinity for the cation binding site observed in the X-ray crystallographic structure with Kdcat = 12 mM, compared with the smaller cation lithium, (Kdcat = 37 mM) and the larger cation cesium (Kd cat = 20 mM). Coupling between cation binding and camphor binding is established by the observation of a linear relationship between the corresponding binding free energies. Potassium binding favours a conformational change of tyrosine 96 which increases the affinity of the protein for camphor and fully dehydrates the active site.

Binding Sites↗