3,4-Methylenedioxy-N-hydroxyamphetamine

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]

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
Chemical and physical data
FormulaC10H13NO3
Molar mass195.218 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NO

References
  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 : PWS. 26 (2): 110–113. doi:10.1023/b:phar.0000018600.03664.36. PMID 15085947.
  2. Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
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