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PubMed1987

Local necrosis and interstitial nephritis due to topical methyl salicylate and menthol.

Excessive percutaneous absorption of potentially toxic substances such as menthol and methyl salicylate may occur through local application of heat, such as the use of a heating pad. Menthol and methyl salicylate are found in nonprescription items and used for muscular and arthritic pains. This patient experienced full-thickness skin and muscle necrosis as well as persistent interstitial nephritis as a result of topical application of methyl salicylate and menthol followed by use of a heating pad, despite the manufacturer's warning against the use of heating pads.

Administration, Cutaneous↗
PubMed2002

[Pharmacokinetics of carvone and menthol after administration of peppermint oil and caraway oil containing enteric formulation].

Enteric coating of peppermint oil/caraway oil capsules avoids subjective discomfort to the patient caused by gastroesophgeal reflux. In order to confirm bioequivalence of an enteric coated formulation containing peppermint oil and caraway oil (Enteroplant) and an immediate release formulation of both oils, the pharmacokinetics of menthol and carvone after oral administration of the two formulations were studied in a randomized, two-period crossover study in 16 healthy male volunteers. The subjects received 180 mg peppermint oil and 100 mg caraway oil, once as 2 enteric coated capsules of the fixed combination preparation Enteroplant containing 90 mg peppermint oil and 50 mg caraway oil each (test) and once in the form of 5 capsules of an immediate release formulation (reference) containing 36 mg peppermint oil and 20 mg caraway oil each. The capsules were taken with 250 ml water after a 10 h fast. Both substances were determined in plasma by GC/MS after extraction. The limit of quantification was 10 ng/ml for menthol and 0.5 ng/ml for carvone. The mean maximum plasma levels for menthol were 1196 ng/ml after administration of the test medication and 1492 ng/ml after administration of the reference medication. The bioavailability with respect to the AUC was comparable after administration of test and reference preparation, the 90% confidence interval was 97 to 105%. As expected, there were considerable differences for Tmax. After application of the enteric coated form the maximum concentration was reached significantly later (3.0 h vs. 1.7 h) compared to the immediate release capsule. Corresponding data were also calculated for carvone. After application of the test medication the maxima of 14 ng/ml for both formulations were reached later (2.5 h vs. 1.3 h). The 90% confidence interval of the AUC for carvone was 79% to 119% and therefore slightly outside the acceptable range for bioequivalence of 80% to 125%. However, this fact should not be relevant, in particular since the dosage of the enteric coated capsule lies at the upper limit of the model text and positive clinical studies, also on the therapeutic equivalence of the two formulations, are available.

Adult↗
PubMed1982

Metabolism of Monoterpenes: Conversion of l-Menthone to l-Menthol and d-Neomenthol by Stereospecific Dehydrogenases from Peppermint (Mentha piperita) Leaves.

The monoterpene ketone l-menthone is specifically converted to l-menthol and l-menthyl acetate and to d-neomenthol and d-neomenthyl-beta-d-glucoside in mature peppermint (Mentha piperita L. cv. Black Mitcham) leaves. The selectivity of product formation results from compartmentation of the menthol dehydrogenase with the acetyl transferase and that of the neomenthol dehydrogenase with the glucosyl transferase. Soluble enzyme preparations, but not particulate preparations, from mature peppermint leaves catalyzed the NADPH-dependent reduction of l-menthone to both epimeric alcohols, and the two dehydrogenases responsible for these stereospecific transformations were resolved by affinity chromatography on Mātrex Gel Red A. Both enzymes have a molecular weight of approximately 35,000, possess a K(m) for NADPH of about 2 x 10(-5)m, are very sensitive to inhibition by thiol-directed reagents, and are not readily reversible. The menthol dehydrogenase showed a pH optimum at 7.5, exhibited a K(m) for l-menthone of about 2.5 x 10(-4)m, and also reduced d-isomenthone to d-neoisomenthol. The neomenthol dehydrogenase showed a pH optimum at 7.6, exhibited a K(m) for l-menthone of about 2.2 x 10(-5)m, and also reduced d-isomenthone to d-isomenthol. These stereochemically distinct, but otherwise similar, enzymes are of key importance in determining the metabolic fate of menthone in peppermint, and they are probably typical of the class of dehydrogenases thought to be responsible for the metabolism of monoterpene ketones during plant development.

Journal Article↗
PubMed1981

GLC analysis of menthol, phenol, benzocaine, and pyrilamine maleate in aerosol spray lotion.

A GLC method is presented for the quantitative determination of menthol, phenol, benzocaine, and pyrilamine maleate. The propellent was exhausted from a pressurized can, and an aliquot of the alcoholic base was weighed. After the addition of the internal standard diluted with chloroform, 1 microliter of the mixture was injected in the chromatograph with a flame-ionization detector and a glass column packed with 2.5% OV-225. Average recoveries were 100.3 +/- 1.4, 100.0 +/- 1.4, 101.3 +/- 1.5, and 101.5 +/- 1.5% for menthol, phenol, benzocaine, and pyrilamine maleate, respectively.

Aerosols↗
PubMed2006

Hepatic UDP-glucose 13C isotopomers from [U-13C]glucose: a simple analysis by 13C NMR of urinary menthol glucuronide.

Menthol glucuronide was isolated from the urine of a healthy 70-kg female subject following ingestion of 400 mg of peppermint oil and 6 g of 99% [U-(13)C]glucose. Glucuronide (13)C-excess enrichment levels were 4-6% and thus provided high signal-to-noise ratios (SNRs) for confident assignment of (13)C-(13)C spin-coupled multiplet components within each (13)C resonance by (13)C NMR. The [U-(13)C]glucuronide isotopomer derived via direct pathway conversion of [U-(13)C]glucose to [U-(13)C]UDP-glucose was resolved from [1,2,3-(13)C(3)]- and [1,2-(13)C(2)]glucuronide isotopomers derived via Cori cycle or indirect pathway metabolism of [U-(13)C]glucose. In a second study, a group of four overnight-fasted patients (63 +/- 10 kg) with severe heart failure were given peppermint oil and infused with [U-(13)C]glucose for 4 hr (14 mg/kg prime, 0.12 mg/kg/min constant infusion) resulting in a steady-state plasma [U-(13)C]glucose enrichment of 4.6% +/- 0.6%. Menthol glucuronide was harvested and glucuronide (13)C-isotopomers were analyzed by (13)C NMR. [U-(13)C]glucuronide enrichment was 0.6% +/- 0.1%, and the sum of [1,2,3-(13)C(3)] and [1,2-(13)C(2)]glucuronide enrichments was 0.9% +/- 0.2%. From these data, flux of plasma glucose to hepatic UDPG was estimated to be 15% +/- 4% that of endogenous glucose production (EGP), and the Cori cycle accounted for at least 32% +/- 10% of GP.

Adult↗
PubMed2006

Desensitization of cold- and menthol-sensitive rat dorsal root ganglion neurones by inflammatory mediators.

The interaction between cold sensitivity and inflammation in mammals is not entirely understood. We have used adult rat dorsal root ganglion neurones in primary culture together with calcium microfluorimetry to assess the effects of selected inflammatory mediators on cold responses of cold- and menthol-sensitive (most likely TRPM8-expressing) neurones. We observed a high degree of functional co-expression of TRPM8, the receptors for the inflammatory agents bradykinin, prostaglandin E2 and histamine, and TRPA1 in cultured sensory neurones. Treatment with either bradykinin or prostaglandin E2 led to a reduction in the amplitude of the response to cooling and shifted the threshold temperature to colder values, and we provide evidence for a role of protein kinases C and A, respectively, in mediating these effects. In both cases the effects were mainly restricted to the subgroups of cold- and menthol-sensitive cells which had responded to the application of the inflammatory agents at basal temperature. This desensitization of cold-sensitive neurones may enhance inflammatory pain by removing the analgesic effects of gentle cooling.

Analgesia↗
PubMed1995

Effects of menthol and cold on histamine-induced itch and skin reactions in man.

The effects of cooling and topical application of menthol on histamine-induced itch, wheal and flare reactions of the left lower arm were investigated in a threefold cross-over design with 15 healthy male volunteers. Lowering skin temperature by cooling from 32.8 +/- 0.3 degrees C to 29.7 +/- 0.5 degrees C reduced itch intensity from 260 +/- 47 units to 55 +/- 12 units (visual analogue scale) and flare diameters from 39.0 +/- 2.0 mm to 30.2 +/- 1.8 mm; wheal reactions were not affected. A similar reduction in itch was found under menthol (42 +/- 14 units) although skin temperature was not decreased. These findings suggest a central inhibitory effect of cold sensitive A-delta fibre activation on itch.

Adult↗
PubMed1993

Evidence of cold receptors in the human bladder: effect of menthol on the bladder cooling reflex.

The effect of menthol on the human bladder cooling reflex was studied prospectively in a group of patients with a positive ice water test. Menthol has a selective potentiating action on cutaneous cold receptors and shifts the temperature response curve of the bladder cooling reflex towards higher temperatures in animal experiments. The substance had an almost identical effect on the human bladder, that is it caused a shift of the threshold temperature of the bladder cooling reflex towards a higher value in all tested patients. Thus, it can be concluded that the human bladder cooling reflex originates from cold receptors within the bladder wall.

Administration, Intravesical↗
PubMed2000

Physicochemical studies of lidocaine-menthol binary systems for enhanced membrane transport.

The melting properties of lidocaine and l-menthol binary systems were studied using differential scanning calorimetry (DSC). A eutectic mixture was obtained for the lidocaine:menthol ratio of 30:70 (w:w) with a eutectic point of 26 degrees C. The binary melt systems formed within a range of 30:70-50:50 (w:w) remained as homogeneous oils at ambient temperature. The solubilities of pure lidocaine and lidocaine from the binary melt systems were determined with and without propylene glycol in pH 8.0 phosphate buffer. Lidocaine from the melt systems was less soluble in the buffers due to the partition of lidocaine between the oil and aqueous phases. The addition of propylene glycol to the buffer significantly increased both the solubility and heat of solubilization of lidocaine. The permeation rates of lidocaine from the binary melt systems across shed snake-skin were concentration dependent and significantly higher than those from the reference solutions.

Anesthetics, Local↗
PubMed2001

Effect of pH on skin permeation enhancement of acidic drugs by l-menthol-ethanol system.

The effect of pH on the skin permeation enhancement of three acidic drugs by the l-menthol-ethanol system was investigated. The total flux of acidic drugs from the system remarkably varied over the pH range 3.0-8.0, and the permeation enhancement factor depended on the system pH and drug. A skin permeation model, which consists of two permeant (unionized and ionized) species, two system (oily and aqueous) phases, and two permeation (lipid and pore) pathways, was developed. The assumptions were made that only the unionized species can distribute to the oily phase and transport via the lipid pathway. The model explained the relationship between the concentration of drug in the aqueous phase and system pH. The skin permeability data were also described by the model and permeability coefficients corresponding to the physicochemical properties of permeant were calculated for the lipid and pore pathways. The model simulation showed that the permeation of acidic drugs occurred from the aqueous phase and the oily phase acted as a reservoir. Whether the total flux increased with increase of pH was dependent on the lipophilicity of drug. These results suggest that the pH of l-menthol-ethanol system should be given attention to elicit the maximum permeation enhancement.

Animals↗
PubMed2003

Influence of menthol and pressure-sensitive adhesives on the in vivo performance of membrane-moderated transdermal therapeutic system of nicardipine hydrochloride in human volunteers.

A membrane-moderated transdermal therapeutic system of nicardipine hydrochloride was developed using 2% w/w hydroxypropylcellulose (HPC) gel as a reservoir system containing 5% w/w of menthol as a penetration enhancer. The permeability flux of nicardipine hydrochloride through the ethylene vinyl acetate (EVA) copolymer membrane was found to increase with an increase in vinyl acetate content in the copolymer. The effect of various pressure-sensitive adhesives (MA-31, MA-38 or TACKWHITE A 4MED on the permeability of nicardipine hydrochloride through EVA 2825 membrane (28% w/w vinyl acetate) or EVA 2825 membrane/skin composite was also studied. The results showed that nicardipine hydrochloride permeability through EVA 2825 membrane coated with TACKWHITE A 4MED/skin composite was higher than that coated with MA-31 or MA-38. Thus, a new transdermal therapeutic system for nicardipine hydrochloride was formulated using EVA 2825 membrane coated with a pressure-sensitive adhesive TACKWHITE A 4MED, and 2% w/w HPC gel as reservoir containing 5% w/w of menthol as a penetration enhancer. In vivo studies in healthy human volunteers indicated that the TTS of nicardipine hydrochloride, designed in the present study, provided steady-state plasma concentration of the drug with minimal fluctuations for 26h with improved bioavailability in comparison with the immediate release capsule dosage form.

Adhesives↗
PubMed1998

Mutagenicity testing (+/-)-camphor, 1,8-cineole, citral, citronellal, (-)-menthol and terpineol with the Salmonella/microsome assay.

The essential oils and their monoterpenoid constituents have been widely used as fragrances in cosmetics, as flavouring food additives, as scenting agents in a variety of household products, as active ingredients in some old drugs, and as intermediates in the synthesis of perfume chemicals. The present study was undertaken to investigate the mutagenic potential of six monoterpenoid compounds: two aldehydes (citral and citronellal), a ketone ((+/-)-camphor), an oxide (1,8-cineole, also known as eucalyptol), and two alcohols (terpineol and (-)-menthol). It is part of a more comprehensive toxicological screening of monoterpenes under way at our laboratory. Mutagenicity was evaluated by the Salmonella/microsome assay (TA97a, TA98, TA100 and TA102 tester strains), without and with addition of an extrinsic metabolic activation system (lyophilized rat liver S9 fraction induced by Aroclor 1254). In all cases, the upper limit of the dose interval tested was either the highest non-toxic dose or the lowest dose of the monoterpene toxic to TA100 strain in the preliminary toxicity test. No mutagenic effect was found with (+/-) camphor, citral, citronellal, 1,8-cineole, and (-) menthol. Terpineol caused a slight but dose-related increase in the number of his+ revertants with TA102 tester strain both without and with addition of S9 mixture. The results from this study therefore suggest that, with the exception of terpineol, the monoterpenoid compounds tested are not mutagenic in the Ames test.

Acyclic Monoterpenes↗
PubMed2003

Lytic activity of l-menthol derivatives against the snow blight disease fungus, Micronectriella nivalis.

Lytic activity of l-menthol (1) derivatives [(-)-(1S,3R,4S,6S)-6-hydroxymenthol (2), (-)-(1S,3R,4S)-1-hydroxymenthol (3), and (+)-(1S,3R,4R,6S)-6,8-dihydroxymenthol (4)] against the snow blight disease fungus, Micronectriella nivalis was investigated. Compounds 2, 3, and 4 had 85.0, 63.9, and 81.9% lytic activity, respectively, at a concentration of 0.2 mg/mL. The activity of each of the three compounds increased in a dose-response manner. To study the structure-activity relationship, acetyl esters of 1-4 [(-)-menthyl acetate (1Ac), (-)-6-hydroxymenthyl diacetate (2Ac), (-)-1-hydroxymenthyl 3-monoacetate (3Ac), and (-)-6,8-dihydroxymenthyl 3,6-diacetate (4Ac)] were synthesized with yields of 80.2-99.8% and were also assayed. The acetyl esters of 1Ac, 2Ac, 3Ac, and 4Ac had 51.2, 91.5, 66.0, and 95.2% lytic activity, respectively, at a concentration of 0.2 mg/mL, and these compounds showed further high lytic activity compared with the alcohols of 1-4. These acetyl esters also showed higher lytic activity as their concentration was increased. Of particular interest is the fact that 2Ac and 4Ac both had higher lytic activity at 0.05-0.2 mg/mL compared with copper 8-hydroxyquinolate, a standard chemical widely used to control snow blight. This is the first report on lytic activity of l-menthol derivatives.

Acetylation↗
PubMed2005

Improvement of table grapes quality and safety by the combination of modified atmosphere packaging (MAP) and eugenol, menthol, or thymol.

Table grape is a nonclimacteric fruit that shows a rapid loss of quality during storage and is very susceptible to colonization by fungi, especially Botrytis cinerea, which is considered the most important disease of this commodity. To solve this problem, synthetic fungicides have been used, although legal restrictions and consumer's concern demand the search of other safe means. In the present paper, and as an alternative of synthetic fungicides, an active packaging to improve MAP effectiveness on preserving table grape (cv. Crimson Seedless) quality and safety was developed by the addition of 0.5 mL of eugenol, thymol, or menthol inside the packages. Packages were stored at 1 degree C for 35 days. The final gas composition inside the packages was 1.4-2.0 and 10.0-14.5 kPa of CO(2) and O(2), respectively, with no significant slight differences among treatments. Results showed that the addition of eugenol, thymol, or menthol improved the beneficial effect of MAP in terms of delaying weight loss and color changes, retarding degrees Brix/acidity ratio evolution, and maintaining of firmness. Thereafter, these treatments showed additional benefit in terms of delayed rates of rachis deterioration and berry decay. Finally, the total viable counts for both mesophilic aerobics and especially yeast and molds were significantly reduced in the grapes packaged with the natural antimicrobial compounds. All of the above effects led to maintenance of table grape quality and safety for longer storage periods (3 additional weeks as compared to controls under MAP only).

Carbon Dioxide↗
PubMed2006

The cold and menthol receptor TRPM8 contains a functionally important double cysteine motif.

We have investigated the glycosylation, disulfide bonding, and subunit structure of mouse TRPM8. To do this, amino-terminal c-myc or hemagglutinin epitope-tagged proteins were incorporated and expressed in Chinese hamster ovary cells. These modifications had no obvious effects on channel function in intracellular calcium imaging assays upon application of agonists, icilin or menthol, and cold temperatures. Unmodified TRPM8 migrates with an apparent mass of 129 kDa and can be glycosylated in Chinese hamster ovary cells to give glycoproteins with apparent masses of 136 and 147 kDa. We identified two potential N-linked glycosylation sites in TRPM8 (Asn-821 and Asn-934) and mutated them to show that only the site in the putative pore region at position 934 is modified and that glycosylation of this site is not absolutely necessary for cell surface expression or responsiveness to icilin, menthol, and cool temperatures. Enzymatic cleavage of the carbohydrate chains indicated that they are complex carbohydrate. The glycosylation site is flanked in the pore by two cysteine residues that we mutated, to prove that they are involved in a conserved double cysteine motif, which is essential for channel function. Mutation of either of these cysteines abolishes function and forces the formation of a non-functional complex of the size of a homodimer. The double cysteine mutant is also non-functional. Finally, we showed in Perfluoro-octanoic acid-polyacrylamide gels that TRPM8 can form a tetramer (in addition to dimer and trimer forms), consistent with current thinking that functional TRP ion channels are tetrameric.

Amino Acid Motifs↗
PubMed2006

Differential expression of capsaicin-, menthol-, and mustard oil-sensitive receptors in naive rat geniculate ganglion neurons.

The roles of capsaicin, menthol, and mustard oils and their receptors in geniculate ganglion (GG) neurons still remain to be elucidated. These receptors belong to the transient receptor potential (TRP) family. Capsaicin-, menthol-, and mustard oil-sensitive receptors are TRPV1, TRPM8, and TRPA1, respectively. The present study aimed to investigate the expression of TRPV1, TRPM8, and TRPA1 in naive rat GG neurons. Furthermore, we examined whether these TRP-expressing GG neurons are myelinated A-fiber or unmyelinated C-fiber neurons. Firstly, using reverse transcription-polymerase chain reaction, TRPV1 mRNA and TRPA1 mRNA were distinctly detected in the naive GG. TRPM8 mRNA was faintly detected. Secondly, using in situ hybridization, TRPV1 mRNA- or TRPA1 mRNA-labeled neurons (signal/noise ratio >or= 10) were observed in 15-20% of GG neurons. Few neurons were labeled by TRPM8 mRNA. Thirdly, neurofilament 200 (NF200) protein, a marker of mylinated A-fiber neurons, was detected in 57% of naive GG neurons. Coexpression of TRPV1 mRNA or TRPA1 mRNA with NF200 was detected in 10% of GG neurons. The present study confirmed the expression of the TRP receptors in the naive GG. The possible roles of TRP receptors in naive GG neurons in somatosensory or gustatory function were suggested.

Animals↗
PubMed2003

A comparative study of the ability of different techniques to extract menthol from Mentha piperita.

Supercritical fluid extraction, direct thermal desorption, hydroalcoholic extraction, and atomization are used to extract menthol from leaf plants of Mentha piperita. The investigated methods are comparatively evaluated on the basis of their reliability to determine the enantiomeric distribution of menthol. The enantioselectivity required for the gas chromatographic analysis is achieved using Octakis (2,6-di-O-n-pentyl-3-O-butyryl)-gamma-cyclodextrin as the stationary phase. From the obtained results, it is established that there is a significant effect of the combination of pressure and temperature to achieve the effective isolation and fractionation of the less and most volatile compounds using supercritical fluids.

Chromatography, Gas↗