DOM: Difference between revisions

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'''2,5-Dimethoxy-4-methylamphetamine''' (also known as '''DOM''' and '''STP''' or '''"Serenity, Tranquility and Peace"''') is a synthetic [[psychoactive class::psychedelic]] substance of the [[substituted amphetamine]] class of chemicals. It is a member of the [[DOx]] family of compounds which are known for their high potency, long duration, and unique mixture of [[psychedelic]] and [[stimulant|stimulating]] effects.{{citation needed}}

DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]] who was investigating the effect of 4-position substitutions on [[psychedelic]] [[amphetamines]].<ref>Shulgin, Alexander (1991). PiHKAL: A Chemical Love Story. Berkeley, CA: Transform Press. pp. 53–56.</ref> It attained some popularity during the summer of 1967 as a psychedelic drug under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>"STP's faster, here's why". Berkeley Barb, June 16-22, 1967. 3-5 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGD19670616.1.3</ref> but widespread human use was short-lived. Subsequently, in 1991, the synthesis and pharmacology of DOM was published in Shulgin's book ''[[PiHKAL]]'' ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.

DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]] who was investigating the effect of 4-position substitutions on [[psychedelic]] [[amphetamines]].<ref name="DOM">Shulgin, Alexander (1991). PiHKAL: A Chemical Love Story. Berkeley, CA: Transform Press. pp. 53–56.</ref> It attained some popularity during the summer of 1967 as a psychedelic drug under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>"STP's faster, here's why". Berkeley Barb, June 16-22, 1967. 3-5 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGD19670616.1.3</ref> but widespread human use was short-lived. Subsequently, in 1991, the synthesis and pharmacology of DOM was published in Shulgin's book ''[[PiHKAL]]'' ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.

This particular substance is part of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds, all of which except [[mescaline]] he developed and synthesized himself. They are found within the first book of PiHKAL and are as follows: [[Mescaline]], DOM, [[2C-B]], [[2C-E]], [[2C-T-2]] and [[2C-T-7]].

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Today, DOM is rarely encountered in the street and is used either as a [[recreational drug]] or as an [[entheogen]].

==History and culture==

DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.<ref name="DOM" />

In mid-1967, tablets containing 20 mg (later 10 mg) of DOM were widely distributed in the Haight-Ashbury District of San Francisco under the name of "STP" (short for "Serenity, Tranquility, and Peace").{{citation needed}}

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 of action (which encouraged some users, familiar with substances 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 it was unknown at the time that the tablets called "STP" were, in fact, DOM.{{citation needed}}

==Chemistry==

DOM, or 4-methyl-2,5-dimethoxyamphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH2) group through an ethyl chain and a methyl group bound to the alpha carbon Rα. DOM contains methoxy functional groups OCH3 attached to carbons R2 and R5 and a methyl group attached to carbon R4 of the phenyl ring.

DOM is the amphetamine analogue of the phenethylamine [[2C-D]].<ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62</ref><ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=68</ref>

==Pharmacology==

@@ Line 4: / Line 4: @@
 '''2,5-Dimethoxy-4-methylamphetamine''' (also known as '''DOM''' and '''STP''' or '''"Serenity, Tranquility and Peace"''') is a synthetic [[psychoactive class::psychedelic]] substance of the [[substituted amphetamine]] class of chemicals. It is a member of the [[DOx]] family of compounds which are known for their high potency, long duration, and unique mixture of [[psychedelic]] and [[stimulant|stimulating]] effects.{{citation needed}}
-DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]] who was investigating the effect of 4-position substitutions on [[psychedelic]] [[amphetamines]].<ref>Shulgin, Alexander (1991). PiHKAL: A Chemical Love Story. Berkeley, CA: Transform Press. pp. 53–56.</ref> It attained some popularity during the summer of 1967 as a psychedelic drug under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>"STP's faster, here's why". Berkeley Barb, June 16-22, 1967. 3-5 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGD19670616.1.3</ref> but widespread human use was short-lived. Subsequently, in 1991, the synthesis and pharmacology of DOM was published in Shulgin's book ''[[PiHKAL]]'' ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.
+DOM was first synthesized and tested in 1963 by [[Alexander Shulgin]] who was investigating the effect of 4-position substitutions on [[psychedelic]] [[amphetamines]].<ref name="DOM">Shulgin, Alexander (1991). PiHKAL: A Chemical Love Story. Berkeley, CA: Transform Press. pp. 53–56.</ref> It attained some popularity during the summer of 1967 as a psychedelic drug under the name "STP" ("Serenity, Tranquility, and Peace"),<ref>"STP's faster, here's why". Berkeley Barb, June 16-22, 1967. 3-5 (Independent Voices) | http://voices.revealdigital.com/cgi-bin/independentvoices?a=d&d=BFBJFGD19670616.1.3</ref> but widespread human use was short-lived. Subsequently, in 1991, the synthesis and pharmacology of DOM was published in Shulgin's book ''[[PiHKAL]]'' ("Phenethylamines I Have Known And Loved")<ref name="PiHKAL">http://www.erowid.org/library/books_online/pihkal/pihkal.shtml</ref>.
 This particular substance is part of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds, all of which except [[mescaline]] he developed and synthesized himself. They are found within the first book of PiHKAL and are as follows: [[Mescaline]], DOM, [[2C-B]], [[2C-E]], [[2C-T-2]] and [[2C-T-7]].
@@ Line 12: / Line 12: @@
 Today, DOM is rarely encountered in the street and is used either as a [[recreational drug]] or as an [[entheogen]].
+==History and culture==
+DOM was first synthesized and tested in 1963 by Alexander Shulgin, who was investigating the effect of 4-position substitutions on psychedelic amphetamines.<ref name="DOM" />
+In mid-1967, tablets containing 20 mg (later 10 mg) of DOM were widely distributed in the Haight-Ashbury District of San Francisco under the name of "STP" (short for "Serenity, Tranquility, and Peace").{{citation needed}}
+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 of action (which encouraged some users, familiar with substances 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 it was unknown at the time that the tablets called "STP" were, in fact, DOM.{{citation needed}}
 ==Chemistry==
 DOM, or 4-methyl-2,5-dimethoxyamphetamine, is a molecule of the [[substituted amphetamine]] class. Amphetamines are substituted phenethylamines containing a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and a methyl group bound to the alpha carbon R<sub>α</sub>. DOM contains methoxy functional groups OCH<sub>3</sub> attached to carbons R<sub>2</sub> and R<sub>5</sub> and a methyl group attached to carbon R<sub>4</sub> of the phenyl ring.
 DOM is the amphetamine analogue of the phenethylamine [[2C-D]].<ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62</ref><ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=68</ref>
 ==Pharmacology==
 {{Further|Serotonergic psychedelic}}