-
Drug Testing and Analysis Feb 2019Psychoactive substances of the 2C-series (2Cs) are phenethylamine-derived designer drugs that can induce psychostimulant and hallucinogenic effects. Chemically, the...
Psychoactive substances of the 2C-series (2Cs) are phenethylamine-derived designer drugs that can induce psychostimulant and hallucinogenic effects. Chemically, the classic 2Cs contain two methoxy groups in positions 2 and 5 of the phenyl ring, whereas substances of the so-called FLY series contain rigidified methoxy groups integrated in a 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran core. One of the pharmacological features that has not been investigated in detail is the inhibition of monoamine oxidase (MAO). Inhibition of this enzyme can cause elevated monoamine levels that have been associated with adverse events such as agitation, nausea, vomiting, tachycardia, hypertension, or seizures. The aim of this study was to extend the knowledge surrounding the potential of MAO inhibition for 17 test drugs, which consisted of 12 2Cs (2C-B, 2C-D, 2C-E, 2C-H, 2C-I, 2C-N, 2C-P, 2C-T-2, 2C-T-7, 2C-T-21, bk-2C-B, and bk-2C-I) and five FLY analogs (2C-B-FLY, 2C-E-FLY, 2C-EF-FLY, 2C-I-FLY, and 2C-T-7-FLY). The extent of MAO inhibition was assessed using an established in vitro procedure based on heterologously expressed enzymes and analysis by hydrophilic interaction liquid chromatography-high resolution tandem mass spectrometry. Thirteen test drugs showed inhibition potential for MAO-A and 11 showed inhibition of MAO-B. In cases where MAO-A IC values were determined, values ranged from 10 to 125 μM (7 drugs) and from 1.7 to 180 μM for MAO-B (9 drugs). In the absence of detailed clinical information on most test drugs, it is concluded that a pharmacological contribution of MAO inhibition cannot be excluded and that further studies are warranted.
Topics: Designer Drugs; Humans; In Vitro Techniques; Inhibitory Concentration 50; Molecular Structure; Monoamine Oxidase; Monoamine Oxidase Inhibitors; Phenethylamines
PubMed: 30188017
DOI: 10.1002/dta.2494 -
Journal of the American Pharmaceutical... Nov 1956
Topics: Acacia; Phenethylamines; Plant Extracts
PubMed: 13376357
DOI: 10.1002/jps.3030451104 -
Food Chemistry Apr 2015Biologically active amines were determined in commercial soybean products. The antioxidant polyamines were found in both non-fermented and fermented soybean products....
Biologically active amines were determined in commercial soybean products. The antioxidant polyamines were found in both non-fermented and fermented soybean products. Natto and tempeh showed the highest content of polyamines (75-124 and 11-24 mg/kg of spermidine and spermine, respectively). On the other hand, the bacterial-related biogenic amines, tyramine, histamine, tryptamine and β-phenylethylamine, were detected in practically all fermented products with a high variability. The highest contents were found in sufu, tamari and soybean paste. Extremely high tyramine and histamine contents, 1700 and 700 mg/kg, respectively, found in some sufu samples could be unhealthy. However, biogenic amines observed in the other soybean products should not be a risk for healthy consumers. However, individuals who take monoamine and diamine oxidase inhibitors drugs should be strongly recommended to avoid this kind of products in order to suffer no adverse health effects. These biogenic amines were not detected in non-fermented soybean products.
Topics: Amines; Biogenic Amines; Chromatography, High Pressure Liquid; Fermentation; Food-Drug Interactions; Histamine; Monoamine Oxidase Inhibitors; Phenethylamines; Risk Assessment; Soy Foods; Spain; Tyramine
PubMed: 25466133
DOI: 10.1016/j.foodchem.2014.10.118 -
European Journal of Pharmacology Nov 1983The conditioned place preference paradigm was used to study the reinforcing properties of beta-phenylethylamine (PEA), d-amphetamine and l-amphetamine. The results...
The conditioned place preference paradigm was used to study the reinforcing properties of beta-phenylethylamine (PEA), d-amphetamine and l-amphetamine. The results confirmed that each drug produced place preferences for a distinctive environment that had previously been paired with the drug treatment. PEA proved as effective as the amphetamine isomers, although substantially less potent. This is the first report of a reinforcing effect of PEA in the rat and supplements previous evidence that PEA is self-administered intravenously in the dog.
Topics: Amphetamine; Animals; Conditioning, Psychological; Dextroamphetamine; Environment; Humans; Male; Phenethylamines; Rats; Reinforcement, Psychology; Stereotyped Behavior
PubMed: 6686144
DOI: 10.1016/0014-2999(83)90653-2 -
Food Chemistry Feb 2017Tyramine is a biogenic compound derived from the decarboxylation of the amino acid tyrosine, and is therefore present at important concentrations in a broad range of raw...
Tyramine is a biogenic compound derived from the decarboxylation of the amino acid tyrosine, and is therefore present at important concentrations in a broad range of raw and fermented foods. Owing to its chemical properties, tyramine can react with nitrite, a common food additive, in the acidic medium of stomach to form N- and C-nitroso compounds. Since toxicology studies have shown that the product of C-nitrosation of tyramine is mutagenic, in the present article tyramine nitrosation mechanisms have been characterized in order to discern which of them are favoured under conditions similar to those in the human stomach lumen. To determine the kinetic course of nitrosation reactions, a systematic study of the nitrosation of ethylbenzene, phenethylamine, and tyramine was carried out, using UV-visible absorption spectroscopy. The results show that, under conditions mimicking those of the stomach lumen, the most favoured reaction in tyramine is C-nitrosation, which generates mutagenic products.
Topics: Benzene Derivatives; Humans; Models, Theoretical; Mutagens; Nitrites; Nitrosation; Nitroso Compounds; Phenethylamines; Stomach; Tyramine
PubMed: 27596392
DOI: 10.1016/j.foodchem.2016.08.006 -
British Journal of Pharmacology Oct 19871 N-(2-cyanoethyl)-2-phenylethylamine (CEPEA) was examined as a possible prodrug of 2-phenylethylamine (PEA). 2 Pharmacokinetics of PEA and CEPEA were investigated in...
1 N-(2-cyanoethyl)-2-phenylethylamine (CEPEA) was examined as a possible prodrug of 2-phenylethylamine (PEA). 2 Pharmacokinetics of PEA and CEPEA were investigated in rat brain, blood and liver by gas chromatography with electron-capture detection (GC-ECD). Interactions of PEA and CEPEA with putative neurotransmitter amines were investigated by use of high performance liquid chromatography with electrochemical detection (h.p.l.c.-e.c.). 3 Administration of PEA caused transient increases in PEA concentrations which decreased rapidly in brain and blood and at a slower rate in liver. Administration of CEPEA caused sustained elevations of PEA concentrations and elimination of PEA was markedly decreased in these tissues relative to the situation after administration of PEA itself. 4 Administration of CEPEA caused more prolonged decreases in brain noradrenaline, dopamine and 5-hydroxytryptamine concentrations than those observed after PEA administration, although values increased to control levels eventually.
Topics: Animals; Brain; Catecholamines; Chromatography, Gas; Electrochemistry; Liver; Male; Monoamine Oxidase; Neurotransmitter Agents; Pharmacokinetics; Phenethylamines; Prodrugs; Rats; Rats, Inbred Strains
PubMed: 2890391
DOI: 10.1111/j.1476-5381.1987.tb11318.x -
Inflammopharmacology Jun 2021Pseudoephedrine (substituted phenethylamine) is well known as psychotic and bronchodilator. Numerous studies on phenethylamine derivatives indicated that these agents...
Anti-rheumatic activity of pseudoephedrine (a substituted phenethylamine) in complete Freund's adjuvant-induced arthritic rats by down regulating IL-1β, IL-6 and TNF-α as well as upregulating IL-4 and IL-10.
Pseudoephedrine (substituted phenethylamine) is well known as psychotic and bronchodilator. Numerous studies on phenethylamine derivatives indicated that these agents have the potential to abolish inflammatory responses in the non-biological and biological systems. These facts provided the basis to conduct a study on pseudoephedrine to explore its therapeutics in Complete Freund's Adjuvant (CFA)-induced arthritis. Furthermore, existing treatment approaches for RA associated with limited effect on chronic immunological models. Real-time polymerase chain reaction (q-PCR) was performed to execute the expression of pro and anti-inflammatory cytokines in treated and non-treated arthritic rats. These findings were further co investigate by histological observations. The paw volume, paw diameter, weight variations and arthritic score were determined at specific days throughout the experiment of 28 days. Pseudoephedrine at all doses significantly (p < 0.001) suppressed the expression of PGE2, TNF-α, IL-1β and IL-6. Moreover, pseudoephedrine (20 and 40 mg/kg) caused significant augmentation of IL-4 and IL-10. Similarly, the drug expressed a significant anti-arthritic effect by reducing the paw volume, paw diameter and arthritic score. Similarly, it also reverts the reduction in body weight of arthritic rats at all above-mentioned doses. These findings supported the anti-arthritic potential of pseudoephedrine and recommended it for clinical trials.
Topics: Animals; Anti-Inflammatory Agents; Antirheumatic Agents; Arthritis, Experimental; Cytokines; Dose-Response Relationship, Drug; Down-Regulation; Freund's Adjuvant; Interleukin-10; Interleukin-1beta; Interleukin-4; Interleukin-6; Phenethylamines; Pseudoephedrine; Rats; Rats, Sprague-Dawley; Tumor Necrosis Factor-alpha
PubMed: 33772383
DOI: 10.1007/s10787-021-00804-z -
Food Additives & Contaminants. Part A,... Mar 2021Biogenic amines (BAs) are natural components of food produced mainly during metabolism in animals and plants. The determination of BAs is important because of their...
Biogenic amines (BAs) are natural components of food produced mainly during metabolism in animals and plants. The determination of BAs is important because of their potential toxicity and their potential use as food spoilage indicators. In the present study, a method for the determination of six BAs (putrescine, cadaverine, histamine, β-phenylethylamine, tyramine, and tryptamine) by Liquid Chromatography - Tandem Mass Spectrometry (LC-MS/MS) with Atmospheric Pressure Chemical Ionisation (APCI) source has been used on trout samples () stored in ice for 15 days. The results showed that on day 15 quite large amounts of putrescine (76.530 mg/kg), cadaverine (85.530 mg/kg), tryptamine (25.210 mg/kg), and histamine (15.975mg/kg) were detected, while the other BAs remained low (β-phenylethylamine: 3.230 mg/kg, tyramine: 0.165mg/kg). Furthermore, microbiological data (Total Vial Count- TVC, , and ) showed that trout samples became organoleptically unacceptable on day 12, while volatile compound analysis showed a significant increase in total amounts of alcohols, aldehydes, and ketones on days 12 and 15.
Topics: Animals; Biogenic Amines; Cadaverine; Colony Count, Microbial; Food Safety; Food Storage; Histamine; Ice; Phenethylamines; Putrescine; Seafood; Solid Phase Extraction; Tandem Mass Spectrometry; Time Factors; Trout; Tryptamines; Tyramine; Volatile Organic Compounds
PubMed: 33481671
DOI: 10.1080/19440049.2020.1865580 -
Acta Crystallographica. Section C,... Jan 1989C8H12N+.C4H5O6-, Mr = 271.27, monoclinic, P21, a = 6.352 (2), b = 14.195 (5), c = 7.507 (2) A, beta = 107.08 (2) degrees, V = 647.0 (8) A3, Z = 2, Dx = 1.39 g cm-3,...
C8H12N+.C4H5O6-, Mr = 271.27, monoclinic, P21, a = 6.352 (2), b = 14.195 (5), c = 7.507 (2) A, beta = 107.08 (2) degrees, V = 647.0 (8) A3, Z = 2, Dx = 1.39 g cm-3, lambda (Mo K alpha) = 0.71069 A, mu (Mo K alpha) = 1.05 cm-1, F(000) = 288, T = 294 K, R = 0.037 for 941 observed reflections [F greater than 2 sigma (F)]. This (+)-tartrate structure is very similar to its meso-tartrate analogue. O(6) occupies an unusual antiperiplanar position relative to the carboxyl group. A strong hydrogen-bond network stabilizes the crystal packing.
Topics: Chemical Phenomena; Chemistry, Physical; Crystallization; Crystallography; Molecular Structure; Phenethylamines
PubMed: 2610953
DOI: 10.1107/s0108270188009710 -
Journal of Medical Toxicology :... Jun 2013The phenethylamines, including 2, 5 dimethoxy-4-iodophenethylamine, commonly referred to as 2C-I, have recently emerged as a new class of designer drugs. Cases of...
The phenethylamines, including 2, 5 dimethoxy-4-iodophenethylamine, commonly referred to as 2C-I, have recently emerged as a new class of designer drugs. Cases of toxicity from these drugs are not well described in the literature. This case report describes a 19 year-old male who insufflated 2C-I. Following the ingestion, the patient developed recurrent seizures, and was taken to the emergency department, where he was noted to be hyperadrenergic and had recurrent seizures. The patient was diagnosed with serotonin syndrome and experienced prolonged respiratory failure, although he ultimately made a full recovery. Comprehensive drug testing revealed the presence of 2C-I. The pharmacologic properties of 2C-I are also discussed.
Topics: Adult; Designer Drugs; Dimethoxyphenylethylamine; Emergency Service, Hospital; Humans; Insufflation; Male; Phenethylamines; Respiratory Insufficiency; Seizures; Serotonin Syndrome; Substance-Related Disorders; Treatment Outcome; Young Adult
PubMed: 23378129
DOI: 10.1007/s13181-013-0287-x