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PubMed1975

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

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.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1992

Evidence that 5-HT2 receptor activation decreases noradrenaline release in rat hippocampus in vivo.

1. Recent electrophysiological studies have shown that 5-HT2/5-HT1C receptor agonists inhibit the electrical activity of noradrenergic neurones in the rat locus coeruleus. Here we examine the effect of various agonists and antagonists of 5-HT2/5-HT1C receptors on noradrenaline release in hippocampus of anaesthetized rats using microdialysis. 2. Subcutaneous administration of the 5-HT2/5-HT1C receptor agonist, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI: 0.2 and 0.5 mg kg-1), caused a marked decrease (50% of pre-drug levels 60 min after injection) of noradrenaline in hippocampal dialysates which was long-lasting (greater than 120 min). Noradrenaline output also decreased in response to administration of the structural analogue of DOI, 1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane (DOB: 1 mg kg-1, s.c.). 3. The effect of DOI on noradrenaline output was prevented by pretreatment with the 5-HT2/5-HT1C receptor antagonist, ritanserin (0.4 mg kg-1, s.c.). Spiperone (0.2 and 1 mg kg-1, s.c.), a 5-HT2/dopamine D2 receptor antagonist which has low affinity for 5-HT1C receptors, also antagonized the effect of DOI (0.5 mg kg-1, s.c.). Sulpiride (50 mg kg-1, s.c.), a dopamine D2 receptor antagonist did not alter the response to DOI (0.5 mg kg-1, s.c.). 4. Both the non-selective 5-HT receptor agonist, quipazine (1 mg kg-1, s.c.), and the 5-HT-releasing agent, p-chloroamphetamine (2 mg kg-1, s.c.), decreased noradrenaline release in hippocampus and these effects were antagonized by pretreatment with ritanserin (0.4 mg kg-1, s.c.).5. Our data suggest that in vivo, noradrenaline release in hippocampus is inhibited by 5-HT2 receptor activation. This effect is probably associated with a decrease in noradrenergic neuronal activity.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1975

A crystallographic and theoretical study of the conformation of DOET and its significance for the hallucinogenic amphetamines.

The crystal and molecular structure of 2, 5-dimethoxy-4-ethyl-alpha-methyl-phenylethylamine (DOET) has been determined by X-ray crystallography and the conformation of the side chain has been examined theoretically by the use of a potential energy calculation. There is no indication in the solid state of any intra or inter-molecular hydrogen bonding. The isopropylamine side chain is staggered to the plane of the benzene ring. The alpha-methyl group is fully extended (antiplanar) whereas the amino group is orientated back towards the ring (synclinal). The potential energy calculations show the existence of 6 minima, one of which corresponds to the crystal position. The calculations also show that the energy differences between the various minima of the side chain are very small. The relationship of these data to the conformations of the hallucinogens, mescaline and 2, 4, 5,-trimethoxyamphetamine is discussed.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1975

Some pharmacological actions of 2,5-dimethoxy-4-ethylamphetamine (DOET) in rats and mice.

DOET, like DOM, exhibited pressor action in rats. This increase of blood pressure was blocked by pretreatment with cinanserin. DOET at high doses decreased the spontaneous locomotor activity of mice at the first hour but increased the activity at the second hour; a low dose was less effective. DOET also increased the rectal temperature of rats and this hyperthermic action was suppressed by pretreating the animals with cinanserin or methysergide. These actions of DOET were compared with those of DOM.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1976

Drug flashbacks. II. Some additional findings.

A subsample was drawn from an earlier collection of data in order to answer a number of questions related to "acid" (LSD, STP) flashbacks. Acid users who reported flashbacks also reported significantly more marijuana use than those who did not; the two groups did not differ on use of other drugs, including acid. Simple correlations and multiple regression analyses both showed extent of marijuana use to be the only drug variable significantly related to acid flashbacks. No optimal combination of marijuana and acid improved flashback prediction. Among acid users, correlations between amounts of use for various drugs were high and significant, excepting only the marijuana-acid correlation.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1976

Discriminative response control by psychomotor stimulants.

Psychomotor stimulants are capable of controlling discriminative responding in rats. Evidence suggests that response control is central, of a fairly specific nature, and dependent on intact dopaminergic functions.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1975

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

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.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗
PubMed1976

Comparison of the effects of R-(-)-2-amino-1-(2,5-dimethoxy-4-methylphenyl) propane (DOM), r-(-)-2-amino-1-(2,5-dimethoxy-4-methylphenyl) butane (BL-3912A) and 5-hydroxytryptamine on non-innervated vascular smooth muscle.

Isolated strips of sheep umbilical arteries contracted in the presence of R-(-)-2-amino-1-(2,5-dimethoxy-4-methylphenyl) butane (BL3912A). These contractions faded over an hour period and at this time BL3912A antagonized contractions to R-(-)-DOM, 5-hydroxytryptamine (5-HT) but not to angiotensin. The initial contraction produced by BL3912A was antagonized by cinanserin, a 5-HT antagonist. These experiments indicate that BL3912A can be classified as a partial agonist of 5-HT receptors in sheep umbilical arteries.

DOM 2,5-Dimethoxy-4-Methylamphetamine↗