View source for 2,5-Dimethoxy-4-methylamphetamine

{{chembox
| ImageFile1 = 2,5-Dimethoxy-4-methylamphetamine.svg
| ImageSize1 = 200px
| ImageFile2 = DOM-3d-sticks.png
| ImageSize2 = 200px
| IUPACName = 1-(2,5-Dimethoxy-4-methylphenyl)-2-aminopropane
| OtherNames = 2,5-Dimethoxy-4-methylamphetamine
| Section1 = {{Chembox Identifiers
| CASNo = 26011-50-7
| CASOther = (R): 43061-13-8<br>(S): 43061-14-9
| PubChem = 
| SMILES = N[C@H](C)CC1=C(OC)C=C(C)C(OC)=C1 (''R''-[[isomer]])
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>12</sub>H<sub>19</sub>NO<sub>2</sub>
| MolarMass = 209.29 g/mol
| Appearance = 
| Density = 
| MeltingPtC = 61
| BoilingPt = 
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards = 
| FlashPt = 
| Autoignition = }}
}}

'''2,5-Dimethoxy-4-methylamphetamine''' ('''DOM''' or '''STP''', allegedly standing for "''Serenity, Tranquility and Peace''", but based on the motor oil company [[STP (motor oil company)|STP]] as named by [[Owsley Stanley]]) is a [[psychedelic]] ([[hallucinogenic drug]]) and a [[substituted amphetamine]]. It was first synthesized by [[Alexander Shulgin]], and later reported in his book ''[[PiHKAL|PiHKAL (Phenethylamines i Have Known And Loved)]]''.  DOM is classified as a [[Controlled Substances Act#Schedule I drugs|Schedule I]] substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the [[Convention on Psychotropic Substances]].<ref>{{cite web |url=http://www.incb.org/pdf/e/list/green.pdf |title= List of psychotropic substances under international control |accessdate= 2007-03-30}}</ref>  It is generally taken orally.

==History==
In mid-1967, tablets containing 20&nbsp;mg (later 10&nbsp;mg) of DOM were widely distributed in the [[Haight-Ashbury|Haight-Ashbury District]] of [[San Francisco]] under the name of STP.  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 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.

==Effects==
Effects of this drug include substantial perceptual changes such as blurred vision, multiple images, vibration of objects, visual hallucinations, distorted shapes, enhancement of details, slowed passage of time, and increased contrasts. It may also cause pupillary dilation and a rise in systolic blood pressure.<ref name=Snyder>{{cite journal |doi=10.1126/science.158.3801.669 |last=Snyder |first=Solomon H. |authorlink= |coauthors=Louis Faillace and Leo Hollister |year=1967 |month=November |title=2,5-Dimethoxy-4-methyl-amphetamine (STP): A New Hallucinogenic Drug |journal=Science |volume=158 |issue=3801 |pages=669–670 |id= |url= |accessdate= |quote= }}</ref>

== Pharmacology ==
DOM is a selective [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[5-HT2B receptor|5-HT<sub>2B</sub>]], and [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]] [[partial agonist]]. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[5-HT2|5-HT<sub>2</sub> receptor]] subfamily.  DOM is a [[Chirality (chemistry)|chiral]] molecule, and ''R''-(-)-DOM is the more active [[enantiomer]], functioning as a potent agonist of the serotonin [[5-HT]] family of receptors; mainly of the [[5-HT2]] subtype.<ref>{{cite journal |last=Sanders-Bush |first=E |authorlink= |coauthors=Burris, KD; Knoth, K |year=1988 |month= |title=Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis |journal=The Journal of pharmacology and experimental therapeutics |volume=246 |issue=3 |pages=924–928 |id= |url= |accessdate= |quote= |pmid=2843634 }}</ref>

;Analogues and derivatives
The 2,6-dimethoxy positional isomer of DOM, known as [[Psi-DOM|Ψ-DOM]], is also mentioned in PiHKAL as being active, as is the alpha-ethyl homologue [[Ariadne (psychedelic)|Ariadne]]. Analogues where the methoxy groups at the 2,5- positions of the aromatic ring have been altered have also been synthesised and tested as part of an effort to identify the binding mode of DOM at the 5-HT<sub>2A</sub> receptor. Both the 2- and 5- O-desmethyl derivatives 2-DM-DOM and 5-DM-DOM, and the 2- and 5- ethyl analogues 2-Et-DOM and 5-Et-DOM have been tested, but in all cases were significantly less potent than the corresponding methoxy compound, showing the importance of the oxygen lone pairs in 5-HT<sub>2A</sub> binding.<ref name="pmid12957227">{{cite journal |author=Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC |title=Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM |journal=Pharmacology, Biochemistry, and Behavior |volume=75 |issue=4 |pages=845–52 |year=2003 |month=July |pmid=12957227 |doi= 10.1016/S0091-3057(03)00159-X|url=}}</ref><ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref>

[[Image:DOM-25-varients.png|280px|thumb|left]]{{clear-left}}

==Toxicity==
Very little is known about the toxicity of DOM. According to Shulgin, the effects of DOM typically last 14 to 20 hours, though other clinical trials indicate a duration of 7 to 8 hours.<ref name=Snyder />

== See also ==
* [[2,5-Dimethoxy-4-Substituted Amphetamine]]s

== References ==
{{More footnotes|date=September 2009}}
{{Reflist|2}}

==External links==
* [http://www.erowid.org/library/books_online/pihkal/pihkal068.shtml DOM Entry in PiHKAL]
* [http://pihkal.info/read.php?domain=pk&id=68 DOM Entry in PiHKAL • info]
* [http://www.erowid.org/chemicals/dom/dom.shtml Erowid DOM Vault]

{{Hallucinogens}}
{{Serotonergics}}
{{Phenethylamines}}

{{DEFAULTSORT:Dimethoxy-4-methylamphetamine, 2,5-}}
[[Category:Serotonin receptor agonists]]
[[Category:Amphetamines]]
[[Category:Phenol ethers]]

{{hallucinogen-stub}}

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[[Category:2Fix]]