What is detected by the HVA metabolite, produced by the organic chemical of the catecholamine and phenethylamine families?
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Homovanillic acid Homovanillic acid (HVA) is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine. Homovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.
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Dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is an organic chemical of the catecholamine and phenethylamine families that plays several important roles in the brain and body. It is an amine synthesized by removing a carboxyl group from a molecule of its precursor chemical L-DOPA, which is synthesized in the brain and kidneys. Dopamine is also synthesized in plants and most animals.
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Para-Chloroamphetamine "para"-Chloroamphetamine (PCA), also known as 4-chloroamphetamine (4-CA), is a substituted amphetamine and monoamine releaser similar to MDMA, but with substantially higher neurotoxicity, thought to be due to the unrestrained release of both serotonin and dopamine by a metabolite. It is used as a neurotoxin by neurobiologists to selectively kill serotonergic neurons for research purposes, in the same way that 6-hydroxydopamine is used to kill dopaminergic neurons.
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Ethyl loflazepate Ethyl loflazepate (marketed under the brand names Meilax, Ronlax and Victan) is a drug which is a benzodiazepine derivative. It possesses anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant properties. In animal studies it was found to have low toxicity, although in rats evidence of pulmonary phospholipidosis occurred with pulmonary foam cells developing with long-term use of very high doses. Its elimination half-life is 51–103 hours. Its mechanism of action is similar to other benzodiazepines. Ethyl loflazepate also produces an active metabolite which is stronger than the parent compound. Ethyl loflazepate was designed to be a prodrug for descarboxyloflazepate, its active metabolite. It is the active metabolite which is responsible for most of the pharmacological effects rather than ethyl loflazepate. The main metabolites of ethyl loflazepate are descarbethoxyloflazepate, loflazepate and 3-hydroxydescarbethoxyloflazepate. Accumulation of the active metabolites of ethyl loflazepate are not affected by those with renal failure or impairment. The symptoms of an overdose of ethyl loflazepate include sleepiness, agitation and ataxia. Hypotonia may also occur in severe cases. These symptoms occur much more frequently and severely in children. Death from therapeutic maintenance doses of ethyl loflazepate taken for 2 – 3 weeks has been reported in 3 elderly patients. The cause of death was asphyxia due to benzodiazepine toxicity. High doses of the antidepressant fluvoxamine may potentiate the adverse effects of ethyl loflazepate.
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Altropane Altropane, (O-587, IACFT, 2β-carbomethoxy-3β-(4-fluorophenyl)-"N"-((E)-3-iodo-prop-2-enyl)tropane) is a phenyltropane derivative which acts as a potent dopamine reuptake inhibitor and long-acting stimulant drug. It has mainly been used as the I radiolabelled form for mapping the distribution of dopamine transporters in the brain, and consequently this has led to its development as a potential diagnostic tool for early detection of Parkinson's disease. It is also being investigated for potential use in the diagnosis and treatment of attention deficit hyperactivity disorder (ADHD).
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Difluoropine Difluoropine (O-620) is a stimulant drug synthesised from tropinone, which acts as a potent and selective dopamine reuptake inhibitor. Difluoropine is unique among the tropane-derived dopamine reuptake inhibitors in that the active stereoisomer is the (S) enantiomer rather than the (R) enantiomer, the opposite way round compared to natural cocaine. It is structurally related to benztropine and has similar anticholinergic and antihistamine effects in addition to its dopamine reuptake inhibitory action.
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2-Methyl-3-oxopropanoic acid 2-Methyl-3-oxopropanoic acid (or methylmalonate semialdehyde) is an intermediate in the metabolism of valine.
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Chocamine Chocamine is a brand of cocoa extract found as an ingredient in many consumer health products, such as NightFood, ChocoMind, ChocoEnergy, LifeMap, Chocoslim, ChocoLift, and ErgoLean AMP. In these consumer products, Chocamine is included to provide the taste, smell and purported health benefits of chocolate, without the sugar, fat, and dairy found in many confectionery products. Cocoa solids contain alkaloids such as theobromine and phenethylamine. Chocamine contains methylxanthine alkaloids (with a high concentration of theobromine), adrenergic amines, amino acids, and some dietary minerals.
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Catechin Catechin is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids.
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Catecholborane Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula CHOBH.
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6-Chloro-MDMA 6-Chloro-MDMA (6-Cl-MDMA, 2-Cl-4,5-MDMA) is a derivative of the amphetamine drug MDMA, which has been identified both in seized "Ecstasy" tablets and in urine samples from drug users. It is thought most likely to be an impurity from synthesis and its pharmacological properties have not been established, however it has been banned in several countries.
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4,4'-Methylenebis(2-chloroaniline) 4,4'-Methylenebis(2-chloroaniline) (MOCA, MBOCA, bisamine) is a substance used as a curing agent in polyurethane production. It is a proven human carcinogen standing on the WHO List of IARC Group 1 carcinogens, with a current threshold limit value of 0.01 ppm in the industrial atmosphere. Animal studies have resulted in tumor growth in the liver, lung, and bladder. Employee exposure is often monitored by measurement of urinary MOCA in free and/or conjugated form.
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Hydroxylammonium chloride Hydroxylammonium chloride is the hydrochloric acid salt of hydroxylamine. Hydroxylamine is a biological intermediate in the nitrification (biological oxidation of ammonia with oxygen into nitrite) and in the anammox (biological oxidation of nitrite and ammonium into dinitrogen gas) which are important in the nitrogen cycle in soil and in wastewater treatment plants.
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DiFMDA Difluoromethylenedioxyamphetamine (DiFMDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, with the aim of finding a non-neurotoxic drug able to be used as a less harmful substitute for entactogenic drugs such as MDMA. Since a major route of the normal metabolism of these compounds is scission of the methylenedioxy ring, producing neurotoxic metabolites such as alpha-methyldopamine, it was hoped that the difluoromethylenedioxy bioisostere would show increased metabolic stability and less toxicity.
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Dihydroxyphenylethylene glycol Dihydroxyphenylethylene glycol (DOPEG) is a metabolite of norepinephrine through monoamine oxidase.
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Dipicolylamine Dipicolylamine is an organic compound with the formula HN(CHCHN). It is a yellow liquid that is soluble in polar organic solvents. The molecule is a secondary amine with two picolyl substituents. The compound is a common tridentate ligand in coordination chemistry.
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Camfetamine Camfetamine (N-methyl-3-phenyl-norbornan-2-amine) is a stimulant drug closely related to the appetite suppressant fencamfamine, being its N-methyl homologue. It has been sold as a designer drug following the banning of mephedrone and related substituted cathinone derivatives in many countries, and reportedly has slightly stronger stimulant effects than fencamfamine, but with correspondingly more severe side effects.
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Halostachine Halostachine (also known as "N"-methylphenylethanolamine) is a natural product, an alkaloid first isolated from the Asian shrub "Halostachys caspica" (synonym "Halostachys belangeriana"), and structurally a β-hydroxy-phenethylamine (a phenylethanolamine) related to its better-known "parent" biogenic amine, phenylethanolamine, to the adrenergic drug synephrine, and to the alkaloid ephedrine. The pharmacological properties of halostachine have some similarity to those of these structurally-related compounds, and "Halostachys caspica" extracts have been included as a constituent of certain OTC dietary supplements, but halostachine has never been developed as a prescription drug. Although it is found in nature as a single stereoisomer, halostachine is more commonly available as a synthetic product in the form of its racemate (see below). In appearance it is a colorless solid.
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Trolamine salicylate Trolamine salicylate (Aspercreme, Aspergel) is an organic compound which is the salt formed between triethanolamine and salicylic acid.
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Methamphetamine Methamphetamine (contracted from "N"-methylamphetamine ) is a strong central nervous system (CNS) stimulant that is mainly used as a recreational drug and less commonly as a treatment for attention deficit hyperactivity disorder and obesity. Methamphetamine was discovered in 1893 and exists as two enantiomers: levo-methamphetamine and dextro-methamphetamine. "Methamphetamine" properly refers to a specific chemical, the racemic free base, which is an equal mixture of levomethamphetamine and dextromethamphetamine in their pure amine forms. It is rarely prescribed due to concerns involving human neurotoxicity and potential for recreational use as an aphrodisiac and euphoriant, among other concerns, as well as the availability of safer substitute drugs with comparable treatment efficacy. Dextromethamphetamine is a much stronger CNS stimulant than levomethamphetamine.
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4-Chlorophenylisobutylamine 4-Chlorophenylisobutylamine (4-CAB, AEPCA), also known as 4-chloro-α-ethylphenethylamine, is an entactogen and stimulant drug of the phenethylamine class. It is an analogue of "para"-chloroamphetamine (PCA) where the alpha position methyl has been replaced with an ethyl group.
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Trimethylamine Trimethylamine (TMA) is an organic compound with the formula N(CH). This colorless, hygroscopic, and flammable tertiary amine has a strong "fishy" odor in low concentrations and an ammonia-like odor at higher concentrations. It is a gas at room temperature but is usually sold in pressurized gas cylinders or as a 40% solution in water. TMA is a nitrogenous base and can be readily protonated to give trimethylammonium cation. Trimethylammonium chloride is a hygroscopic colorless solid prepared from hydrochloric acid. Trimethylamine is a good nucleophile, and this reaction is the basis of most of its applications.