2,5-Dimethoxy-4-methylamphetamine

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists DOM's dose as 3 to 10mg orally and its duration as 14 to 24hours. An estimated typical dose is about 6mg. DOM is said by Shulgin to have a slow build-up, with an onset of 30 to 60minutes and a peak of 2 to 6hours. At low doses, such as 1 to 4mg, DOM produced effects including stimulation, euphoria, enhanced self-awareness, and mild dose-dependent perceptual disturbances. At higher doses, of above 5 to 7mg, DOM produces marked and full psychedelic effects. Hallucinogenic effects were said to start at doses of more than 3 to 5mg. Other effects of the drug were also described. Although Shulgin described the effects of DOM as typically lasting 14 to 20hours, clinical studies with low doses reported a duration of only 5 to 8hours, but with a lack of an unexpectedly long duration even at doses of up to 14mg. Another source listed the average duration as only 8 to 15hours at doses of 5 or 10mg. The reasons for these discrepancies are unclear. The onset was 0.5 to 1.5hours and peak effects occurred after 3 to 5hours. Low doses of DOM have been used as a stimulant, such as by the Grateful Dead. This may be the first known instance of psychedelic microdosing. The related drug DOET is also implicated as having stimulant and "psychic energizer" effects at low doses, which notably greatly impressed Shulgin. ==Interactions==

The typical antipsychotic and serotonin 5-HT2A receptor antagonist chlorpromazine has been reported to partially reduce the effects of DOM. ==Side effects==

Side effects of DOM include sweating, muscle tremors, and large increases in heart rate. In one study, in which five people were given 6mg DOM for 3days, there were "extremely intense" effects the first day, but diminished effects on the third day, ranging from "moderately strong" to "felt absolutely nothing". In another study, in which two people were given gradually increasing doses from 1 to 12mg over 8days, there was development of marked partial tolerance to the effects of DOM. Tolerance developed to both the psychoactive and physiological effects of the drug. ==Overdose==

Overdose of DOM can have a very long duration and result in an amphetamine psychosis-like state. It is said to have pronounced hallucinogenic effects as well as amphetamine-like side effects in overdose. ==Pharmacology==

Pharmacodynamics Actions DOM acts as a selective serotonin 5-HT2A, 5-HT2B, and 5-HT2C receptor full agonist. The drug is inactive as a human trace amine-associated receptor 1 (TAAR1) agonist but is an agonist of the rhesus monkey TAAR1. DOM is inactive as a monoamine reuptake inhibitor and releasing agent. It is a very weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A), whereas it was inactive at monoamine oxidase B (MAO-B). Effects DOM produces the head-twitch response in rodents, a behavioral proxy of psychedelic-like effects. The head-twitch response produced by DOM is robust. Conversely however, DOC has shown reinforcing effects, including conditioned place preference (CPP) and self-administration, in rodents similarly to methamphetamine. This is analogous to other findings in which various 2C and NBOMe drugs have been found to produce dopaminergic elevations and reinforcing effects in rodents. DOM has potent anti-inflammatory effects, which may have medical applications. Pharmacokinetics The pharmacokinetics of DOM, including in humans, have been very limitedly studied. They might contribute to the delayed onset and long duration of DOM in humans. About 5 to 20% of a dose of DOM is excreted unchanged in humans. ==Chemistry==

DOM, also known as 2,5-dimethoxy-4-methylamphetamine or as 2,5-dimethoxy-4-methyl-α-methylphenethylamine, is a substituted phenethylamine and amphetamine and is a member of the DOx group of drugs. Properties The chemical properties of DOM have been described. }} ==History==

DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines. His 15-year-old son Theodore "Ted" Shulgin assisted in the synthesis of DOM by performing the first step of the synthesis at Dow Chemical Company on June 22, 1963 during a brief period when he was interested in chemistry. Later, Alexander Shulgin completed the synthesis on November 30, 1963. He initially discovered the effects of DOM on January 4, 1964, when he ingested a 1mg dose orally. The hallucinogenic effects of DOM were discovered on February 3, 1964 by Shulgin's colleague Thornton W. Sargent when he ingested 2.3mg. The first clearly psychedelic experience occurred with a dose of 4.1mg on November 6, 1964. Shulgin hoped that Dow Chemical Company would develop DOM for medical purposes. In mid-1967, tablets containing 20mg and later 10mg of DOM were widely distributed in the Haight-Ashbury District of San Francisco under the name of STP, having been manufactured by underground chemists Owsley Stanley and Tim Scully. This short-lived appearance of DOM on the black market proved disastrous for several reasons. First, the tablets contained an excessively high dose of the chemical. This, combined with DOM's slow onset (which encouraged some users, familiar with drugs that have quicker onsets, such as LSD, to re-dose) and its remarkably long duration, caused many users to panic and sent some to the emergency room. Second, treatment of such overdoses was complicated by the fact that no one at the time knew that the tablets called STP were, in fact, DOM, and there was no effective antidote. ==Society and culture==

Names The name DOM is an acronym of the code name "des-oxy-methyl" coined by the drug's inventor Alexander Shulgin. Legal status Australia DOM is schedule 9 under the Australia Poisons standard. A schedule 9 substance is a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities." United Kingdom DOM is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971. United States DOM is Schedule I in the United States. This means it is illegal to manufacture, buy, possess, or distribute (make, trade, own or give) without a DEA license. ==Research==

DOM, along with DOET, was of interest in the potential treatment of psychiatric disorders such as depression in the 1960s. Subsequently, the related compound Ariadne (4C-D; BL-3912; Dimoxamine) was investigated in the 1970s, but was not marketed either. ==See also==