Biomaterial Database

Metabolic O-demethylation of the psychotomimetic amine 1-(2, 5-dimetroxy-4-methylphenyl)-2-aminopropane. 1975

J S Zwieg, and N Castagnoli

In an effort to more fully characterize the metabolic fate of the psychotomimetic amine (1-(2, 5-dimethoxy-4-methylpheny.)-2-aminopropane (DOM, STP), the formation of the two possible monophenols and the p-hydroquinone metabolites of the parent drug by 10,000 X g supernatent fractions of rabbit liver homogenates has been investigated. All three metabolites have been fully characterized and quantitatively estimated by chemical ionization mass spectrometry with the aid of deuterium enriched compounds. The stereochemical course of the mono-O-demethylation reactions has been shown to proceed with enantiomeric enrichment of the S-aminophenols. The mechanistic implications concerning the mode of action of the parent drug and metabolic O-demethylation are discussed.

UI	MeSH Term	Description	Entries
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D007536	Isomerism	The phenomenon whereby certain chemical compounds have structures that are different although the compounds possess the same elemental composition. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Isomerisms
D008099	Liver	A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances.	Livers
D011809	Quinones	Hydrocarbon rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.
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
D003640	Dealkylation	The removing of alkyl groups from a compound. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Dealkylations
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
D006892	Hydroxydopamines	Dopamines with a hydroxy group substituted in one or more positions.	Hydroxydopamine
D000662	Amphetamines	Analogs or derivatives of AMPHETAMINE. Many are sympathomimetics and central nervous system stimulators causing excitation, vasopressin, bronchodilation, and to varying degrees, anorexia, analepsis, nasal decongestion, and some smooth muscle relaxation.
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia