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{{Short description|Psychedelic amphetamine}}
{{Drugbox
{{DISPLAYTITLE:3,4-Methylenedioxy-''N''-hydroxyamphetamine}}
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| IUPAC_name = (±)-1-(benzo[d][1,3]dioxol-5-yl)-''N''-hydroxylpropan-2-amine
{{Infobox drug
| image = Methylenedioxyhydroxyamphetamine.png
| drug_name = 3,4-Methylenedioxy-''N''-hydroxyamphetamine
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| width = 200px
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| IUPAC_name = 1-(1,3-Benzodioxol-5-yl)-''N''-hydroxypropan-2-amine
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| CAS_number = 74698-47-8
| image = MDOH_structure.svg
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| ATC_prefix =
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| width = 200px
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| ATC_suffix =
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| PubChem = 98528
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| DrugBank =
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| ChemSpiderID = 88979
| chemical_formula = C<sub>10</sub>H<sub>13</sub>NO<sub>3</sub>
| molecular_weight = 195.22 g/mol
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| smiles = CC(CC1=CC2=C(C=C1)OCO2)NO
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| bioavailability =
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =
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| pregnancy_category=
| legal_status =
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| routes_of_administration =
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}}


<!--Clinical data-->
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'''3,4-Methylenedioxy-''N''-hydroxyamphetamine''' ('''MDOH''', '''MDH''') is an [[entactogen]], [[psychedelic_drug|psychedelic]], and [[stimulant]] of the [[substituted phenethylamine|phenethylamine]] and [[substituted amphetamine|amphetamine]] [[chemical class]]es. It is the ''N''-[[hydroxy]] [[homology (chemistry)|homologue]] of [[methylenedioxyamphetamine|MDA]], and the ''N''-[[desmethyl]] homologue of [[methylenedioxyhydroxymethamphetamine|MDHMA]]. MDOH was first [[synthesized]] and [[assay]]ed by [[Alexander Shulgin]].<ref>{{CitePiHKAL}}</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>{{CitePiHKAL}}</ref> He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature.<ref>{{CitePiHKAL}}</ref> He also mentioned several negative side effects also seen with [[MDMA]] ("Ecstasy") such as difficulty urinating and internal dryness.<ref>{{CitePiHKAL}}</ref>
| tradename =
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| pregnancy_category =
| legal_CA = Schedule I
| legal_UK = Class A
| legal_DE = Anlage I
| legal_US = Schedule I
| legal_UN = P I
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| routes_of_administration =


<!--Pharmacokinetic data-->
== See also ==
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| bioavailability =
* [[Substituted Methylenedioxyphenethylamine]]
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| protein_bound =
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| metabolism =
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| elimination_half-life =
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| excretion =

<!--Identifiers-->
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| CAS_number = 74698-47-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = SJE1T2B1A7
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| ATC_prefix = none
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| ATC_suffix =
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| PubChem = 98528
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| DrugBank =
| KEGG = C22807
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| ChemSpiderID = 88979

<!--Chemical data-->
| C=10 | H=13 | N=1 | O=3
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| smiles = CC(CC1=CC2=C(C=C1)OCO2)NO
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}}

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'''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&nbsp;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" />


== 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|state=expanded}}

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{{Entactogens}}
{{Hallucinogens}}
{{Hallucinogens}}
{{Stimulants}}
{{Stimulants}}
{{Monoamine releasing agents}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Phenethylamines}}
{{Phenethylamines}}
{{MDxx}}



{{DEFAULTSORT:Methylenedioxy-N-hydroxyamphetamine, 3, 4-}}
{{pharmacology-stub}}
[[Category:Substituted amphetamines]]
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[[Category:Designer drugs]]
[[Category:Benzodioxoles]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
[[Category:Entactogens and empathogens]]
[[Category:Hydroxylamines]]
[[Category:Human drug metabolites]]


[[Category:Psychedelic phenethylamines]]
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[[Category:Amphetamines]]


{{nervous-system-drug-stub}}
[[ru:MDOH]]

Latest revision as of 03:41, 10 May 2024

3,4-Methylenedioxy-N-hydroxyamphetamine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NO

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]
  1. ^ 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.
  2. ^ 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.
[edit]


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