Biomaterial Database

N-Hydroxylation of 1-(2,5-demethoxy-4-methylphenyl)-2-aminopropane by rabbit liver microsomes. 1975

J Gal, and L D Gruenke, and N Castagnoli

Metabolic N-hydroxylation of the potent psychotomimetic amine 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (5) by rabbit liver microsomal preparations has been investigated. Synthetic hydroxylamine 8 was obtained by sequential reduction of the corresponding nitropropene 10 with sodium borohydride followed by zinc reduction of the resulting nitropropane 11. Compound 8 in water (pH 7.4) was rapidly air oxidized to oxime 12; this oxidation was completely blocked by rabbit liver microsomes. Microsomal incubations of amine 5 or its bis(methoxy-d3)hexadeuterio analog 5-d6 resulted in the formation of 8 and 8-d6, respectively, identified as their bis(trifluoroacetyl) derivatives by GLC-MS. Quantitative estimations of metabolite formation employing selected ion monitoring with the aid of an accelerating voltage alternator were accomplished by stable isotope dilution analyses with 5-d6 as substrate and 8-d0 as internal standard. Similar analyses starting with "pseudoracemates" (R)-5-d0:(S)-5-d6 or (R)-5-d6:(S)-5-d0 as substrates established metabolite 8 to be enriched with its R enantiomer.

UI	MeSH Term	Description	Entries
D008297	Male		Males
D008862	Microsomes, Liver	Closed vesicles of fragmented endoplasmic reticulum created when liver cells or tissue are disrupted by homogenization. They may be smooth or rough.	Liver Microsomes,Liver Microsome,Microsome, Liver
D008968	Molecular Conformation	The characteristic three-dimensional shape of a molecule.	Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D010091	Oximes	Compounds that contain the radical R2C	Aldoximes,Hydroxyimino Compounds,Ketoxime,Ketoximes,Oxime,Compounds, Hydroxyimino
D011817	Rabbits	A burrowing plant-eating mammal with hind limbs that are longer than its fore limbs. It belongs to the family Leporidae of the order Lagomorpha, and in contrast to hares, possesses 22 instead of 24 pairs of chromosomes.	Belgian Hare,New Zealand Rabbit,New Zealand Rabbits,New Zealand White Rabbit,Rabbit,Rabbit, Domestic,Chinchilla Rabbits,NZW Rabbits,New Zealand White Rabbits,Oryctolagus cuniculus,Chinchilla Rabbit,Domestic Rabbit,Domestic Rabbits,Hare, Belgian,NZW Rabbit,Rabbit, Chinchilla,Rabbit, NZW,Rabbit, New Zealand,Rabbits, Chinchilla,Rabbits, Domestic,Rabbits, NZW,Rabbits, New Zealand,Zealand Rabbit, New,Zealand Rabbits, New,cuniculus, Oryctolagus
D002849	Chromatography, Gas	Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix.	Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D003903	Deuterium	The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	Deuterons,Hydrogen-2,Hydrogen 2
D004290	DOM 2,5-Dimethoxy-4-Methylamphetamine	A psychedelic phenyl isopropylamine derivative, commonly called DOM, whose mood-altering effects and mechanism of action may be similar to those of LSD.	2,5-Dimethoxy-4-Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine (DOM),1-(2,5-Dimethoxy-4-Methylphenyl)-2-Aminopropane,2 5 DOM,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine Hydrochloride, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (+,-)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (R)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, (S)-Isomer,2,5-Dimethoxy-4-Methylamphetamine, Hydrochloride,2,5 Dimethoxy 4 Methylamphetamine,2,5-Dimethoxy-4-Methylamphetamine, DOM,DOM 2,5 Dimethoxy 4 Methylamphetamine
D006898	Hydroxylamines	Organic compounds that contain the (-NH2OH) radical.
D006900	Hydroxylation	Placing of a hydroxyl group on a compound in a position where one did not exist before. (Stedman, 26th ed)	Hydroxylations