3,4-Methylenedioxy-N-hydroxyamphetamine: Difference between revisions
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{{Short description|Psychedelic amphetamine}} |
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{{Drugbox |
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{{DISPLAYTITLE:3,4-Methylenedioxy-''N''-hydroxyamphetamine}} |
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{{Infobox drug |
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| image = 3,4-MDOH.png |
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| drug_name = 3,4-Methylenedioxy-''N''-hydroxyamphetamine |
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| image = MDOH_structure.svg |
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| width = 200px |
| width = 200px |
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| tradename = |
| tradename = |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_CA = Schedule I |
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| legal_UK = Class A |
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| legal_DE = Anlage I |
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| legal_US = Schedule I |
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| legal_UN = P I |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number = 74698-47-8 |
| CAS_number = 74698-47-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = SJE1T2B1A7 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = 98528 |
| PubChem = 98528 |
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| DrugBank = |
| DrugBank = |
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| KEGG = C22807 |
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| ChemSpiderID = 88979 |
| ChemSpiderID = 88979 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=10 | H=13 | N=1 | O=3 |
| C=10 | H=13 | N=1 | O=3 |
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| molecular_weight = 195.22 g/mol |
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| smiles = CC(CC1=CC2=C(C=C1)OCO2)NO |
| smiles = CC(CC1=CC2=C(C=C1)OCO2)NO |
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'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH''') is an [[entactogen]], [[ |
'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH''', '''N-hydroxytenamphetamine''') is an [[entactogen]], [[psychedelic drug|psychedelic]], and [[stimulant]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es.<ref name="de_Boer_2004">{{cite journal | vauthors = de Boer D, Bosman I | title = A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs | journal = Pharmacy World & Science | volume = 26 | issue = 2 | pages = 110–113 | date = April 2004 | pmid = 15085947 | doi = 10.1023/b:phar.0000018600.03664.36 }}</ref> It is the ''N''-[[hydroxyl|hydroxy]] [[Homologous series|homologue]] of [[3,4-Methylenedioxyamphetamine|MDA]], and the ''N''-[[desmethyl]] homologue of [[methylenedioxyhydroxymethamphetamine|MDHMA]]. MDOH was first [[Organic synthesis|synthesized]] and [[assay]]ed by [[Alexander Shulgin]].<ref name = "CitePiHKAL">{{CitePiHKAL|name-list-style = vanc }}</ref> In his book ''[[PiHKAL]]'' (''Phenethylamines i Have Known And Loved''), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours.<ref name = "CitePiHKAL" /> He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.<ref name = "CitePiHKAL" /> He also mentioned several negative side effects also seen with [[MDMA]] ("Ecstasy") such as difficulty urinating and internal dryness.<ref name = "CitePiHKAL" /> |
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== See also == |
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* [[Substituted methylenedioxyphenethylamines]] |
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== References == |
== References == |
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* [http://pihkal.info/read.php?domain=pk&id=114 MDOH entry in PiHKAL • info] |
* [http://pihkal.info/read.php?domain=pk&id=114 MDOH entry in PiHKAL • info] |
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{{Entactogens}} |
{{Entactogens|state=expanded}} |
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{{Hallucinogens}} |
{{Hallucinogens}} |
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{{Stimulants}} |
{{Stimulants}} |
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{{Monoamine releasing agents}} |
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{{Adrenergics}} |
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{{Dopaminergics}} |
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{{Serotonergics}} |
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{{Phenethylamines}} |
{{Phenethylamines}} |
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{{DEFAULTSORT:Methylenedioxy-N-hydroxyamphetamine, 3, 4-}} |
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[[Category:Substituted amphetamines]] |
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[[Category:Benzodioxoles]] |
[[Category:Benzodioxoles]] |
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[[Category:Serotonin-norepinephrine-dopamine releasing agents]] |
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[[Category:Entactogens and empathogens]] |
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[[Category:Hydroxylamines]] |
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[[Category:Human drug metabolites]] |
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{{nervous-system-drug-stub}} |
Latest revision as of 03:41, 10 May 2024
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Chemical and physical data | |
Formula | C10H13NO3 |
Molar mass | 195.218 g·mol−1 |
3D model (JSmol) | |
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3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes.[1] It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin.[2] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours.[2] He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.[2] He also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.[2]
References
[edit]- ^ de Boer D, Bosman I (April 2004). "A new trend in drugs-of-abuse; the 2C-series of phenethylamine designer drugs". Pharmacy World & Science. 26 (2): 110–113. doi:10.1023/b:phar.0000018600.03664.36. PMID 15085947.
- ^ a b c d Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
External links
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