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4,4’-Dimethylaminorex

Brain

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4,4’-Dimethylaminorex - (4,4’-DMAR; 4-methyl-5-(4-methylphenyl)-4,5-dihydrooxazol-2-amine) is a synthetic substituted derivative of oxazoline, classified as an analog of aminorex and 4-methylaminorex. Aminorex is listed as Schedule IV of the 1971 United Nations Convention on Psychotropic Substances. A new synthetic psychostimulant 4,4’- DMAR was first found in November 2012 in the Netherlands, and after a while it spread all over Europe. Differences in chemical structure between the two psychostimulants are due to the presence of methyl groups. So, Aminorex doesn't have any methyl groups, while 4-methylaminorex has 4-position methyl group in oxazoline ring. Sometimes it is called «Serotoni», "Speckled Cherry", "Speckled Cross" on the streets. It is a designer entactogen with psychostimulant properties. 4,4’-DMAR has a molecular formula C11H14N2O, it has two chiral centers in oxazoline ring, which allows for formation of 4 enantiomers. Some other names of the substance include: 4-Methyl-5-(4-methylphenyl)-4,5-dihydrooxazol-2-amine; 4-Methyl-5-(p-tolyl)-4,5-dihydrooxazol-2-amine; 4,5-Dihydro-4-methyl-5-(4-methylphenyl)-2-oxazolamine; [4-Methyl-5-(p-tolyl)-2-oxazolin-2-yl]amine; 4-Methyl-5-(para-methylphenyl)-2-amino-oxazoline; para-Methyl-4-methylaminorex; p-Methyl-4-methylaminorex; 4-Methylaminorex; p-methyl derivative; 4,4′-Dimethylaminorex; p4-DMAR; 4-methyl-euphoria; 4-methyl-U4Euh; 4-M-4-MAR; ST; ST60; ICE; McN-822; 4-MAX.

Synthesis of 4,4'-DMAR


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Cis- and trans- free base racemates derived from the same precursor 4'-methyl-norephedrine by means of cyanogen bromide for synthesis of both products, which were described as colorless and solid substances. Cis- and trans- free base forms have a melting point of 136-138 °C and 101-103 °C, respectively, while the water-soluble form of hydrochloride has a melting point of 163-165 °C. Cis-4,4'-DMAR is a white crystalline powder available as a research chemical in online chemistry stores. The contents of the tablets, which usually have a high concentration of 4,4'-DMAR, can vary from product to product because they can have the substance in different concentrations and together with other substances, which have similar mechanism of action; for example, tablets may contain a certain amount of synthetic kathinones, synthetic cannabinoids, benzofuranes or ethylphenidates, which influences both kinetics and dynamics of the substance in human body. According to EMCDDA, as of 2015 there were a lot of cases of dangerous side effects and a lot of lethal outcomes, associated with its use.
Pharmacodynamics and pharmacokinetics.
To this date, there aren't any studies on pharmacodynamic effects of 4,4'-DMAR on the human body. After intravenous administration maximum concentration of the substance is reached after 15 minutes with a rapid decrease in its concentration during four hours, the half-life is about 46.5 minutes. After administration, the substance spreads rapidly to the brain tissue and reaches its maximum concentration in 30-60 minutes with a brain-to-plasma ratio of 24, which is associated with fairly good lipophilicity (logP 5 1.5). As for the metabolism, the process begins with hydroxylation, hydrolysis and oxidative deamination. The metabolite formed as a result of hydrolysis is a parameterized derivative of norephedrine, which is a psychoactive substance used as a stimulant, decongestant and anorexigenic agent. This fact suggests that the metabolite may have similar activity.

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In addition, oxidation and aromatic hydroxylation are metabolic pathways characteristic of amphetamine-like compounds. However, the main metabolite detected both in plasma and in the brain tissue, was formed by oxidation of the paramethyl group of cis-4,4-DMAR. In studies on 4,4'-DMAR in rats it was revealed that cis-4.4'-DMAR was a powerful releaser of dophamine, noradrenaline and serotonin. The dose-response curve for DAT, NET and SERT was determined, EC50=8.6 nm, 26.9 nm and 18.5 nm, respectively. The study also showed a DAT/SERT ratio with an indicator of 2. In terms of 4,4'-DMAR influence on the synaptosomes of the rat brain, it was found that the substance had a much more powerful dophamine- and noradrenaline-releasing activity than MDMA. Interestingly, cis-4,4’-DMAR acts as fully effective releaser, at the same time trans-4,4’-DMAR acts as absorption blocker. Binding of 4,4′-DMAR to 5-HT2A-receptor causes some mild hallucinogenic effects, similar to that of MDMA.

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In studies on mice it was proved that 4,4'-DMAR induces dose-dependent psychomotor agitation, increased sweating, salivation, hyperthermia, stimulated aggression, seizures and death. cis- 4,4'-DMAR is less active in terms of acute toxicity effects than its transform. Immunohistochemical analysis determines that acute intoxication with this substance induces high expression of oxidative/nitrosative stress markers (8-OHdG, iNOS, NT and NOX2), apoptosis markers (Smac/DIABLO и NF-κB) and heat shock proteins (HSP27, HSP70, HSP90) in frontal cortex, which indicates a potential neurotoxic effect of the substance. Studies on excretion in urine revealed, that the deterioration of physiological and neurobehavioral parameters may be associated with inhibition of cis-4,4′-DMAR from metabolism at equivalent dose for a human of 0.486 mg/kg, which corresponds with low toxicity level, euphoric effects, decrease in appetite, heart rate and motor activity increase. Equivalent dose for a human 2.12 - 3.15 mg/kg corresponds to average effects with potentiation of standard acute toxicity effects, which involve the following symptoms: anxiety, agitation, insomnia, bruxism, etc. Higher doses 14-20 mg/kg are associated with classical clinical picture of acute toxicity due to psychostimulants consisting of fatal cardio-vascular system disorders and death.

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Psychomotor agitation, increased spontaneous motor activity, and a pattern of "unusual hyperactivity" observed in mice, are a classical presentation of initial effects of 4,4'-DMAR. In terms of pharmacology, it coincides with an increase in extracellular monoamine levels, especially in the dorsal and ventral striatum. Hyperthermia after 4,4'-DMAR intake occurs due to its influence on 5HT2A-receptors. Hyperthermia is potentiated by motor activity and increased metabolism, which, in turn, increases the risk of side effects and serotonin syndrome. Alternatively, increased level of norepinephrine can also underlie hypertheric effect. Its mechanism of action leads to impairment in heat loss due to vasoconstriction caused by α1AR, the stimulation of the adrenergic receptors α1 and β3 regulates mitochondrial protein in skeletal muscles, uncoupling the protein UCP-3, causing thermogenesis. Hyperthermia as a whole is considered potentially acute severe side effect and one of the main causes of death. Systemic administration of cis-4,4'-DMAR at a dose of 30 mg/kg causes lethal outcome in 50% of mice. Total tonic contractions of the entire musculature and convulsions occur before death. Such proconvulsive properties of this substance may be associated with its greater affinity and blocking activity in regard to SERT and monoamine transporters. In studies of Valavanidis it was revealed that mice administered 4-4'-DMAR in high doses had increased expression of 8-OHdG, which is a marker of oxidative damage to DNA, as well as other similar markers. This fact serves as the basis for the assumption of definite damage to the body by active forms of nitrogen, as well as the development of nitrosative stress. Official sources report, that after non-lethal 4,4’-DMAR toxicity in 14-year-old girl, the concentration of the substance in blood was 0,448 mg/l. The symptoms included dilated pupils and anxiety. As for the lethal cases, there were reports on 8 deaths in Hungary, 1 death in Poland and 23 deaths in the UK. The concentration in postmortem biological samples varied from 0,02 to 18, 68 mg/l in blood, from 5.93 to 43.9 mg/l in urine.
Clinical effects of 4,4’-DMAR.
According to ACMD and EVCDDA, desirable effects include euphoria, increased sociability and energy, alertness and self-confidence, while undesirable effects range from palpitations, hyperthermia, sweating, arousal, bruxism, facial spasms, stimulation, dysphoria and dilated pupils to psychosis and hallucinations. Desirable effects of 4,4'-DMAR include psychostimulation, which is described as almost identical to amphetamine action, but as less pronounced in equivalent doses, which is explained by a certain mechanism of action and affinity to receptors; pronounced euphoria and apathy similar to that of MDMA, but less pronounced; anxiety reduction is registered after intake of low or medium doses of the substance; increased empathy and desire to communicate; improved control over the body; wakefulness; the effect of "time distortion", increased libido; acceleration of thought and increased motivation; the effect of "ego inflation" when administered in medium doses, as well as a feeling of "drifting" with deformation and slight distortion of dynamic objects; increased endurance and decreased appetite.

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Negative undesirable effects include: dry mouth, dehydration, increased blood pressure, development of anxiety and paranoia (even in small doses due to the specific mechanism of action), increased heart rate, change in emotions, increased sweating, disorders of the gastrointestinal tract with dyspepsia symptoms, disorder of hydrochloric acid synthesis with changes in stomach pH, bronchodilation, frequent urination or inability to urinate due to spasm, bruxism, temporary erectile dysfunction, muscle spasms and convulsions, "restless legs" syndrome, the development of a transient subdepressive state, temperature regulation impairment, uncontrollable increase in body temperature, the effect of "vibrating vision", psychosis, the occurrence of depersonalization (unlikely), cognitive fatigue, headache, the occurrence of malignant arterial hypertension, cold extremities due to peripheral vascular spasms of the microcirculatory bed and impaired blood outflow from the veins, arrhythmia with impaired AV conduction, transient coronary spasm, toxic encephalopathy (in high doses).​

Methods of use and doses.
When administered orally by gelatin capsules (or by swallowing tablets containing the substance or powder, wrapped in cigarette paper beforehand, «bombing») minimum dose of 4,4′‐DMAR starts with 0.8-2.1 mg/kg. The initial effects are described as a gradual change in vision, the development of some illusions on the periphery of the view, mood improvement, empathy, mild or moderate psychostimulation. The initial effects begin 10-20 minutes after use and reach their peak in 45-60 minutes with rapid leveling. Medium dose when administered orally range from 2.2 to 3.15 mg/kg. More pronounced psychostimulation and appearance of illusions up to mild hallucinations (visual and auditory) are added to the effects above. Other side effects include anxiety and paranoia; high dose of the substance starts with 4 mg/kg. When administered intranasally the minimum effective dose of pure 4,4′‐DMAR, associated with certain effects, is 0.5-0.8 mg/kg, medium dose is 1.2-1.9 mg/kg. High dose of the substance administered intranasally is 2.5 mg/kg and more.

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Special instructions and interactions.
It is not recommended to use 4,4′‐DMAR together with vitamin K antagonists, antidepressants, clonidine, b-blockers (excluding sympathomimetic action), hypertensive agents, halogenated anesthetics, alcohol and anticonvulsants. Also, the joint use of this substance with antibacterial drugs of the aminoglycoside group, tetracyclines and macrolides is not recommended. Absolute contrandications of 4,4′‐DMAR use include severe vascular atherosclerosis, any symptomatic cardiovascular disease, course of MAOis (and 14 days after the last intake of a drug of this group), glaucoma, hyperthyroidism.

After use, it is advisable to monitor blood pressure, pulse and body temperature every hour. It is absolutely necessary to restore the water-electrolyte balance. For this purpose, chloride-bicarbonate-sodium water is used in a volume of about three liters within 24 hours. If it is impossible to empty the bladder, it is recommended to take a warm bath, drink an antispasmodic agent. For preventive purposes, 24 hours before the act of use, it is necessary to start taking a course of proton pump inhibitors, magnesium preparations (preferably combination of asparaginate and orotate), ascorbic acid at a dose of 500 mg per day and continue taking these drugs for at least 5 days after the act of use. Intranasal use is always associated with damage to the mucous membranes. To reduce the risks of developing consequences, it is necessary to wash the nose with a slightly saturated saline solution every 30 minutes for preventive purposes, perform respiratory exercises with acts of forced exhalation, use herbal preparations that include such components as yellow gentian, spring primrose, acetosa, sorrel, black elderberry, verbena officinalis.​

Low risk when used together with 4,4’-DMAR (or amplification of 4,4’-DMAR effects): N2O, MDMA, amphetamine, cocaine and other psychostimulants.
High risk when used together with 4,4’-DMAR: DOx, NBOMes, 2C-T-x, 5-MeO-xxT, DXM, PCP.
Extremely high risk when used together with 4,4’-DMAR: αMT, tramadol, MAOis, mushrooms, LSD, DMT, mescaline, 2C-x, cannabis, ketamine, MXE, Caffeine, Alcohol, GHB/GBL, opioids.
 
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