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DOM: Difference between revisions
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==Chemistry== | ==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, 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 name=":0">http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=62</ref><ref>http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=68</ref> | ||
This is one of the last of the experimental compounds within the phenethylamine family on which any animal toxicity studies were performed prior to human studies. The <abbr>LD50</abbr> of DOM is between 100 - 125 mg/kg for a mouse. An effective dose in a human of 2 mg (for an 80 kg man) is equivalent to 25 μg/kg. | |||
As with DOI, the presence of a heavy atom, the bromine atom, in DOB makes the radioactive isotope labelled material a powerful research tool.<ref name=":0" /> | |||
==Pharmacology== | ==Pharmacology== | ||
{{Further|Serotonergic psychedelic}} | {{Further|Serotonergic psychedelic}} | ||
DOM is a selective [[agonist|partial agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] family. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors, but less so on the 5-HT<sub>2C</sub> receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] subfamily. | DOM is a selective [[agonist|partial agonist]] at the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] family. Its psychedelic effects are mediated by its [[agonist]]ic properties at the 5-HT<sub>2A</sub> and 5-HT<sub>2B</sub> receptors, but less so on the 5-HT<sub>2C</sub> receptor. Due to its selectivity, DOM is often used in scientific research when studying the [[Serotonin#The 5-HT System|5-HT<sub>2</sub> receptor]] subfamily. DOM is a [[Chirality|chiral]] molecule, and ''R''-(-)-DOM is the more active [[enantiomer]], functioning as a potent agonist of the serotonin family of receptors (mainly of the 5-HT<sub>2</sub> subtype).<ref>Sanders-Bush, Burris, KD; Knoth, K, (September 1988). "Lysergic acid diethylamide and 2,5-dimethoxy-4-methylamphetamine are partial agonists at serotonin receptors linked to phosphoinositide hydrolysis" http://www.ncbi.nlm.nih.gov/pubmed/2843634</ref> However, the role of these interactions and how they result in the psychedelic experience continues to remain elusive. | ||
DOM is | 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-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>Eckler JR, Chang-Fong J, Rabin RA, Smith C, Teitler M, Glennon RA, Winter JC (July 2003). "Behavioral characterization of 2-O-desmethyl and 5-O-desmethyl metabolites of the phenylethylamine hallucinogen DOM". ''Pharmacology Biochemistry and Behavior''. '''75''' (4): 845–52. doi:10.1016/S0091-3057(03)00159-X. <nowiki>PMID 12957227</nowiki>. S2CID 36463979.</ref> | ||
There is a strong implication that some metabolic conversion occurs in the lung, and it is only after this that the truly active metabolite is available for central action. This is consistent with the relatively slow onset of effect, and the very long duration of action.<ref name=":0" /> | |||
==Subjective effects== | ==Subjective effects== | ||