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N -Methyltyramine

N-Methyltyramine, chemically known as 4-hydroxy-N-methylphenethylamine, is a naturally occurring protoalkaloid with the molecular formula C₉H₁₃NO and a molecular weight of 151.21 g/mol. It serves as an N-methylated derivative of tyramine, functioning as a trace amine in biological systems and exhibiting roles in stimulating gastrin release to promote appetite and digestion. Found in plants such as Acacia species (up to 0.5% dry weight), Citrus aurantium (bitter orange, comprising 3–4% of protoalkaloids), malted barley (up to 2 mg/g), and certain cacti, it also occurs in fermented alcoholic beverages like beer at concentrations around 2 mg/L, arising from microbial activity during production.^[1]^[2] Biosynthetically, N-methyltyramine is derived from L-tyrosine through decarboxylation to tyramine followed by N-methylation, a process mediated by enzymes such as phenylethanolamine N-methyltransferase in animals or tyramine N-methyltransferase in plants like barley. In plants, it can further methylate to form hordenine, contributing to secondary metabolite pathways, while in humans and mice, it appears as an endogenous metabolite involved in metabolic regulation. Its presence in foods and beverages underscores its dietary relevance, with absorption occurring efficiently in the small intestine (>90% in rats) and rapid hepatic metabolism leading to urinary excretion.^[3]^[1]^[2] Pharmacologically, N-methyltyramine acts primarily as an α₂-adrenoreceptor antagonist, inhibiting lipolysis (fat breakdown) and potentially elevating blood pressure through norepinephrine release, though it lacks the direct cardiovascular mimicry of catecholamines like norepinephrine. It stimulates pancreatic and gastric secretions at low doses (e.g., 25 µg/kg in rats), supporting its traditional use in anti-shock treatments alongside synephrine in herbal medicines like Fructus Aurantii immaturus. Safety profiles indicate low toxicity, with LD₅₀ values of 780 mg/kg (intraperitoneal) and 275 mg/kg (intravenous) in mice, and no reported harm to ruminants at dietary levels. Despite these effects, its role in supplements (e.g., from bitter orange extracts) warrants caution due to potential interactions with adrenergic systems.^[1]^[2]

History

Discovery and Isolation

N-Methyltyramine was first synthesized in 1910 by G. S. Walpole during studies on phenolic amines, although its structure was not fully characterized at that time.^[4] Walpole's work involved the identification of related compounds like tyramine in botanical sources, hinting at the presence of N-methylated derivatives in certain plant materials. This early observation laid groundwork for later investigations into trace alkaloids in flora. The compound was isolated and characterized for the first time in 1950 from germinating barley roots (Hordeum vulgare) by Edward Leete, Sam Kirkwood, and Léo Marion.^[5] They extracted the alkaloid from 600 g of roots after 10 days of growth following germination, yielding 168 mg of pure N-methyltyramine, marking the first natural isolation of this protoalkaloid. This discovery was detailed in their seminal paper in the Journal of the American Chemical Society, which emphasized its role as a precursor in alkaloid biogenesis, briefly referencing its formation from tyramine in the plant.^[5] Initial identification of N-methyltyramine relied on classical extraction techniques followed by chromatographic methods. In barley, Leete, Kirkwood, and Marion employed solvent extraction and fractional crystallization for purification, confirmed by melting point analysis and derivative formation.^[5] Subsequent early detections in Acacia species, such as Acacia berlandieri, utilized paper chromatography, thin-layer chromatography, and gas chromatography to separate and identify it alongside tyramine and hordenine in leaf extracts.^[6] These methods established N-methyltyramine's occurrence in diverse botanical sources during the mid-20th century.

Biosynthesis

N-Methyltyramine is primarily biosynthesized through the enzymatic N-methylation of tyramine, where S-adenosyl methionine (SAM) serves as the methyl donor.^[7] This reaction is catalyzed by tyramine N-methyltransferase (EC 2.1.1.27), which transfers the methyl group from SAM to the nitrogen atom of tyramine, yielding N-methyltyramine, S-adenosylhomocysteine, and a proton.^[7] The overall reaction can be represented as:

\text{tyramine} + \text{S-adenosyl-L-methionine} \rightarrow \text{N-methyltyramine} + \text{S-adenosyl-L-homocysteine} + \text{H}^+

This pathway is prominent in plants, particularly during the germination of seeds, where tyramine—derived from the decarboxylation of tyrosine—is converted to N-methyltyramine as an intermediate in the formation of more complex alkaloids like hordenine. The biosynthetic role was confirmed in 1953 through isotope labeling experiments showing formation from tyramine in barley seedlings.^[8] In barley (Hordeum vulgare) seedlings, two distinct SAM-dependent N-methyltransferases facilitate the stepwise methylation: the first produces N-methyltyramine from tyramine, and the second dimethylates it to hordenine, with activity concentrated in young roots during early growth stages.^[9] Similar N-methylation pathways occur in other alkaloid-producing plants, such as species of Acacia, where tyramine serves as the precursor for phenethylamine-derived alkaloids. Secondary biosynthetic routes for N-methyltyramine have been identified in certain fungi and bacteria, often involving phenethylamine intermediates that undergo decarboxylation and subsequent N-methylation.^[10] In fungi like those producing nonribosomal peptides (e.g., Paramyrothecium and Colletotrichum species), dedicated N-methyltransferases such as LcsG catalyze iterative N-methylation starting from phenethylamine-like moieties, incorporating N-methyltyramine into larger metabolites like leucinostatins or xylomyrocins.^[11] Bacterial production of trace amines, including N-methyltyramine, follows analogous methylation steps from tyramine or phenethylamine precursors, though these pathways are less characterized and typically linked to secondary metabolism in soil microbes or fermented food contexts.^[12]

Chemistry

Structure and Properties

N-Methyltyramine, also known as 4-[2-(methylamino)ethyl]phenol, is a phenolic amine derivative of tyramine featuring a methyl group attached to the nitrogen atom of the ethylamine side chain.^[13] Its chemical formula is C₉H₁₃NO, with a molecular weight of 151.21 g/mol.^[13] The compound appears as colorless plates and exists as a crystalline solid at room temperature. It has a melting point of 130–131.5 °C and is soluble in water and hot absolute ethanol.^[14] Spectroscopic analysis confirms its structure: in the ¹H NMR spectrum (D₂O, with DSS as internal standard), the aromatic protons of the para-substituted benzene ring appear at δ 7.24 and δ 6.90 ppm, while the N-methyl group resonates at δ 2.61 (3H), and the methylene groups at δ 3.16 (2H) and δ 2.94 (2H). The IR spectrum shows characteristic absorptions for the aromatic ring at 1610, 1593, and 1511 cm⁻¹, and for the phenolic OH stretch at approximately 3300 cm⁻¹.^[14]

Synthesis

N-Methyltyramine can be synthesized through several laboratory methods, with classical approaches focusing on stepwise construction of the phenethylamine backbone followed by selective N-methylation. One early method involves the reduction of 4-hydroxyphenylacetamide to tyramine, followed by N-methylation of the primary amine group using methyl iodide or similar alkylating agents.^[15] This two-step process, reported in 1910, yields the target compound after purification, often as the hydrochloride salt, and was pivotal for early physiological studies of the amine.^[15] A synthetic route starts from commercially available 4-methoxyphenethylamine, which is first N-methylated (typically with methyl iodide in the presence of a base) to form N-methyl-4-methoxyphenethylamine, and then undergoes selective O-demethylation using hydrobromic acid or boron tribromide to afford N-methyltyramine. This method protects the phenolic hydroxyl during N-functionalization and provides a higher overall yield compared to unprotected routes, making it suitable for preparative scales.

Salts and Basicity

N-Methyltyramine is an amphoteric compound owing to its phenolic hydroxyl group, which can donate a proton, and its secondary amine group, which can accept a proton, leading to distinct protonation equilibria in aqueous solutions.^[13] This dual functionality allows the molecule to exist in zwitterionic or charged forms depending on the pH, with the phenolic group exhibiting acidic behavior and the amine group basic behavior.^[1] The pKa values reflect this acid-base character: the phenolic hydroxyl has a pKa of 10.54 (predicted), while the conjugate acid of the amine (ammonium ion) has a pKa of 9.82 (predicted).^[1] These values indicate that at physiological pH (~7.4), the amine is predominantly protonated (as RNH₃⁺), while the phenolic group remains deprotonated. The basicity of the amine is governed by the equilibrium:

\text{RNH}_2 + \text{H}^+ \rightleftharpoons \text{RNH}_3^+

where R represents the 4-hydroxyphenethyl group, and the pKa of 9.82 corresponds to the ammonium ion dissociation.^[1] Common salt forms of N-methyltyramine include the hydrochloride, which is widely used due to its stability and solubility properties. The hydrochloride salt has a melting point of 141–149 °C and is highly water-soluble, facilitating its use in pharmaceutical and supplement formulations.^[16] These salts enhance the compound's handling and bioavailability by improving solubility in polar solvents compared to the free base, which has limited water solubility (~3.4 g/L, predicted).^[1]

Occurrence

In Plants

N-Methyltyramine occurs in various plant species as a secondary metabolite involved in alkaloid biosynthesis pathways, where it serves as an intermediate derived from tyramine via methylation by plant enzymes.^[17] High concentrations have been reported in Acacia species, with levels of approximately 0.5% dry weight in seeds.^[2] It is also present in germinating barley (Hordeum vulgare) roots at up to 1960 μg/g and in bitter orange (Citrus aurantium) at approximately 180 μg/g in ripe fruit.^[2]^[18] Additionally, it has been isolated from several cacti, including Ariocarpus retusus, Ariocarpus kotschoubeyanus, and Obregonia denegrii.^[19]^[20]^[21] Quantification of N-methyltyramine in plant extracts typically employs high-performance liquid chromatography (HPLC) or gas chromatography-mass spectrometry (GC-MS), often coupled with tandem mass spectrometry (LC-MS/MS) for enhanced sensitivity and specificity in identifying trace levels within complex matrices.^[22] These methods allow for accurate measurement of its distribution across plant tissues, confirming its role in species like Acacia and Citrus.

In Foods and Beverages

N-Methyltyramine occurs in beer as a result of barley fermentation, with concentrations in commercial samples ranging from 0.59 to 4.61 mg/L.^[23] These levels remain stable throughout mashing, fermentation, and conditioning, contributing to human exposure in the low milligram range upon moderate consumption.^[23] In processed barley products, N-methyltyramine is present in trace amounts, reaching up to 2 mg/g in malted barley depending on the malting conditions and malt type. This compound, derived from barley used in brewing, exemplifies its dietary presence in fermented grain-based foods. N-Methyltyramine in alcoholic beverages, particularly beer, acts as a stimulant for gastrin release, with beer containing sufficient levels (around 2 mg/L) to elicit this effect during ingestion. For instance, consumption of 750 mL of beer by a 60 kg individual delivers approximately 25 μg/kg body weight of N-methyltyramine. As a biogenic amine, N-methyltyramine is monitored under food safety standards for fermented beverages like beer, where regulatory limits on total biogenic amines help mitigate potential health risks from accumulation.^[24]

Pharmacology

Mechanism of Action

N-Methyltyramine (NMT) acts as an agonist at trace amine-associated receptor 1 (TAAR1), a Gs-coupled receptor expressed in various brain regions and peripheral tissues, where it stimulates adenylyl cyclase to increase intracellular cAMP levels. This activation modulates monoaminergic neurotransmission by enhancing the release and inhibiting the reuptake of neurotransmitters such as dopamine, norepinephrine, and serotonin, with EC50 values for NMT at human TAAR1 reported in studies ranging from approximately 2–23 μM, comparable to tyramine (around 1–10 μM depending on the assay).^[25]^[26]^[27] The potency of NMT at TAAR1 is comparable to that of tyramine but generally lower than β-phenylethylamine, positioning it as a moderate endogenous trace amine ligand that influences sympathetic tone and central nervous system functions. NMT also serves as an antagonist at α-adrenoreceptors, particularly the α2 subtype, with inhibitory effects observed in binding assays using radiolabeled ligands like [3H]p-aminoclonidine on mouse brain membranes (IC50 ≈ 10-5 M). By blocking presynaptic α2-adrenoreceptors on sympathetic nerve terminals, NMT disrupts the autoinhibitory feedback loop that normally attenuates norepinephrine release in response to nerve stimulation. This antagonism thereby potentiates norepinephrine efflux from sympathetic nerves, contributing to elevated sympathetic activity and associated pressor responses in experimental models.^[28] In adipocytes, NMT inhibits stimulated lipolysis, suppressing the breakdown of triglycerides into free fatty acids and glycerol more potently than insulin in human primary cells. This effect involves interference with the activation of hormone-sensitive lipase (HSL), a serine esterase phosphorylated by protein kinase A to initiate lipolysis downstream of β-adrenergic signaling. Although the precise pathway linking NMT to HSL inhibition is not fully characterized, it occurs independently of TAAR1, which is absent in adipose tissue, and manifests at concentrations relevant to dietary exposure (0.01–1 mM).^[29]

Physiological Effects

N-Methyltyramine displays pressor activity, elevating blood pressure through sympathomimetic effects. In canine models, intravenous administration at 0.25 mg/kg markedly increases peripheral resistance, while infusion at 0.04 mg/kg/min raises mean arterial pressure and renal vascular resistance.^[2] This compound's pressor potency is approximately 1/140 that of epinephrine, as determined in early pharmacological studies using dogs, where it was characterized as an effective agent for inducing vasoconstriction and cardiac stimulation. The compound potently stimulates gastrin release, promoting digestive processes. In anesthetized rats, oral doses achieve an ED50 of ~10 μg/kg for gastrin secretion, with maximal effects at 25 μg/kg, sufficient to account for the gastrin-releasing activity observed in beer consumption.^[30] This action enhances appetite and nutrient digestion by triggering cholinergic reflexes that increase pancreatic secretions.^[2] N-Methyltyramine exhibits potential antilipolytic effects in adipose tissue, inhibiting fat mobilization. In human adipocytes derived from surgical samples, it suppresses isoprenaline-induced lipolysis more potently than insulin, significantly reducing glycerol release (p < 0.05–0.001) at concentrations of 0.01–1 mM, while showing minimal direct lipolytic activity itself.^[31] These inhibitory properties, mediated partly through α2-adrenoreceptor antagonism, suggest a role in limiting lipid breakdown and supporting lipid storage, with implications for weight management.^[2] As a TAAR1 agonist, N-methyltyramine may contribute to neuromodulation in the central nervous system, similar to other trace amines.^[32]

Pharmacokinetics

Absorption and Distribution

N-Methyltyramine exhibits rapid oral absorption primarily in the small intestine. In rat models, over 90% of an orally administered dose (20 mg/kg) is absorbed, predominantly in the duodenum, jejunum, and ileum.^[33] Upon entering the bloodstream, N-methyltyramine distributes extensively and rapidly to various tissues. In rabbits following intravenous administration, the distribution kinetics follow a two-compartment model with an α-phase half-life of 0.3 minutes and a β-phase half-life of 5.6 minutes, reflecting quick equilibration between plasma and tissues. The apparent volume of distribution is 1.79 L/kg, indicating broad tissue penetration facilitated by its moderate lipophilicity (logP ≈ 0.48).^[34]^[35] N-Methyltyramine also penetrates the blood-brain barrier to a limited extent. In mice, radiolabeled tracer studies detected the compound in brain tissue shortly after administration, suggesting potential for central nervous system effects despite its peripheral predominance.^[34]

Metabolism and Elimination

N-Methyltyramine is primarily metabolized via N-demethylation to tyramine, followed by oxidative deamination catalyzed by monoamine oxidase (MAO) enzymes, yielding 4-hydroxyphenylacetic acid as the major metabolite.^[36] This biotransformation occurs predominantly in the liver, contributing to its short duration of action.^[36] Oral bioavailability of N-methyltyramine is limited by extensive hepatic first-pass metabolism, estimated at approximately 50%, resulting in systemic exposure of about 30–50% of the administered dose in rat models.^[33] Absorption exceeds 90% in the small intestine, but the pronounced first-pass effect significantly attenuates circulating levels.^[33] Elimination is rapid, with a terminal half-life of 5.6 minutes in rabbits following intravenous administration.^[34] In these animal studies, over 80% of the radiolabeled dose is recovered in urine within 1 hour, indicating efficient renal clearance primarily as metabolites, with negligible amounts remaining in tissues after this period.^[34]

Toxicology

Acute Toxicity

N-Methyltyramine exhibits low acute toxicity in animal models, with reported LD50 values of 780 mg/kg via intraperitoneal administration and 275 mg/kg via intravenous administration in mice.^[2] These values indicate a low risk of lethality at typical exposure levels but highlight potential hazards with higher doses, particularly through parenteral routes. It is not considered toxic to ruminants at typical dietary levels.^[2] At high doses, N-methyltyramine can induce symptoms such as hypertension and tachycardia, primarily due to its sympathomimetic effects that mimic catecholamine release and elevate cardiovascular activity.^[2] These acute responses underscore the compound's pressor mechanism, which contributes to immediate cardiovascular risks in overdose scenarios. Under the Globally Harmonized System (GHS), N-methyltyramine is classified as harmful if swallowed (H302), causing severe skin burns and eye damage (H314), and may cause respiratory irritation (H335).^[13]

Safety Concerns

N-Methyltyramine, as a trace amine structurally similar to tyramine, may pose a risk of hypertensive crisis similar to the "cheese effect" when consumed by individuals taking monoamine oxidase inhibitors (MAOIs), due to its pressor effects that can lead to sudden elevations in blood pressure through norepinephrine release.^[29]^[37] This interaction emphasizes the need for caution in patients on MAOI therapy for conditions like depression. The use of N-methyltyramine in weight loss supplements lacks robust scientific evidence supporting its safety or efficacy, with potential adverse effects including elevated blood pressure reported in limited studies.^[38] Furthermore, it is prohibited by the World Anti-Doping Agency (WADA) under the category of specified stimulants, having been added to the banned list in 2015 to prevent its use in competitive sports.^[39] N-Methyltyramine is not approved by the U.S. Food and Drug Administration (FDA) for any therapeutic or supplemental use, and in 2024, the FDA classified it as a new dietary ingredient requiring premarket notification due to lack of history of safe use.^[40]^[41] Its presence in dietary products has prompted regulatory warnings due to undeclared inclusion and safety risks. In the European Union, it is monitored as a biogenic amine in foods, with recommended limits for related compounds like tyramine generally below 200 mg/kg to mitigate toxicity risks in fermented products.^[42]

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