2,5-Dimethoxy-4-methylamphetamine
Encyclopedia
2,5-Dimethoxy-4-methylamphetamine (commonly referred to as DOM or on the street as STP, allegedly standing for 'Serenity, Tranquility, and Peace', but based on the motor oil company STP
as named by Owsley Stanley
) is a psychedelic
and a substituted amphetamine
. It was first synthesized by Alexander Shulgin
, and later reported in his book PiHKAL: A Chemical Love Story
. DOM is classified as a 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
. It is generally taken orally.
, 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.
, 5-HT2B
, and 5-HT2C receptor
partial agonist
. Its psychedelic effects are mediated by its agonist
ic properties at the 5-HT2A receptor. Due to its selectivity, DOM is often used in scientific research when studying the 5-HT2 receptor subfamily. DOM is a 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.
Analogues and derivatives
The 2,6-dimethoxy positional isomer of DOM, known as Ψ-DOM
, is also mentioned in PiHKAL as being active, as is the alpha-ethyl homologue 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-HT2A 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-HT2A binding.
STP (motor oil company)
STP is an American brand and trade name for the automotive additives, lubricants and performance division of Armored AutoGroup.Founded in 1953 in Saint Joseph, Missouri, the company’s name, STP, was derived from “Scientifically Treated Petroleum”...
as named by Owsley Stanley
Owsley Stanley
Owsley Stanley also known as Bear, was an essential and transitional personality in the development of the San Francisco Bay counter-culture. Spanning the Beat-era years of Ken Kesey's Merry Pranksters scenes, he was equally pivotal to the explosion of 1960's Psychedelia culture...
) is a psychedelic
Psychedelic drug
A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...
and a substituted amphetamine
Substituted amphetamine
Substituted amphetamines are a chemical class of stimulants, entactogens, hallucinogens, and other drugs. They feature a phenethylamine core with a methyl group attached to the alpha carbon resulting in amphetamine, along with additional substitutions...
. It was first synthesized by Alexander Shulgin
Alexander Shulgin
Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
, and later reported in his book PiHKAL: A Chemical Love Story
PiHKAL
PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens...
. DOM is classified as a 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
Convention on Psychotropic Substances
The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, benzodiazepines, and psychedelics signed at Vienna on February 21, 1971...
. It is generally taken orally.
History
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. 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 LSDLSD
Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...
, 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, increased sexual drive and pleasure, and increased contrasts. It may also cause pupillary dilation and a rise in systolic blood pressure.Pharmacology
DOM is a selective 5-HT2A5-HT2A receptor
The mammalian 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor . This is the main excitatory receptor subtype among the GPCRs for serotonin , although 5-HT2A may also have an inhibitory effect on certain areas such...
, 5-HT2B
5-HT2B receptor
5-hydroxytryptamine receptor 2B, also known as HTR2B, is a 5-HT2 receptor, but also denotes the human gene encoding it.-Function:...
, and 5-HT2C receptor
5-HT2C receptor
The 5-HT2C receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gq/G11 and mediates excitatory neurotransmission. HTR2C denotes the human gene encoding for the receptor, that in humans is located at the...
partial agonist
Partial agonist
Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist...
. Its psychedelic effects are mediated by its agonist
Agonist
An agonist is a chemical that binds to a receptor of a cell and triggers a response by that cell. Agonists often mimic the action of a naturally occurring substance...
ic properties at the 5-HT2A receptor. Due to its selectivity, DOM is often used in scientific research when studying the 5-HT2 receptor subfamily. DOM is a chiral
Chirality (chemistry)
A chiral molecule is a type of molecule that lacks an internal plane of symmetry and thus has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom....
molecule, and R-(-)-DOM is the more active enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
, functioning as a potent agonist of the serotonin 5-HT family of receptors; mainly of the 5-HT2 subtype.
Analogues and derivatives
The 2,6-dimethoxy positional isomer of DOM, known as Ψ-DOM
Psi-DOM
Ψ-DOM, or 2,6-dimethoxy-4-methylamphetamine, is a hallucinogenic drug and a structural isomer of the better-known hallucinogen DOM. Ψ-DOM was first reported by Alexander Shulgin in his book PiHKAL ....
, is also mentioned in PiHKAL as being active, as is the alpha-ethyl homologue Ariadne
Ariadne (psychedelic)
Ariadne , or 4-methyl-2,5-dimethoxy-alpha-ethylphenethylamine, is a lesser-known psychedelic drug. It is a homologue of 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin...
. 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-HT2A 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-HT2A binding.