3-Hydroxy-4-methoxyamphetamine

3-Hydroxy-4-methoxyamphetamine
Clinical data
Other names4-Methoxy-3-hydroxyamphetamine
ATC code
  • None
Identifiers
  • 5-(2-aminopropyl)-2-methoxyphenol
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C=C1)OC)O)N
  • InChI=1S/C10H15NO2/c1-7(11)5-8-3-4-10(13-2)9(12)6-8/h3-4,6-7,12H,5,11H2,1-2H3
  • Key:IHPFVQVCJHQPFN-UHFFFAOYSA-N

3-Hydroxy-4-methoxyamphetamine is an amphetamine and a known metabolite of the entactogen MDMA in rodents and humans. The essential oil analogues and precursors are chavibetol and isochavibetol, and can be converted into 3-hydroxy-4-methoxyamphetamine via amination.

See also

References

  1. ↑ Helmlin HJ, Bracher K, Bourquin D, Vonlanthen D, Brenneisen R (October 1996). "Analysis of 3,4-methylenedioxymethamphetamine (MDMA) and its metabolites in plasma and urine by HPLC-DAD and GC-MS". Journal of Analytical Toxicology. 20 (6): 432–440. doi:10.1093/jat/20.6.432. PMID 8889680.
  2. ↑ De Martinis BS, Barnes AJ, Scheidweiler KB, Huestis MA (June 2007). "Development and validation of a disk solid phase extraction and gas chromatography-mass spectrometry method for MDMA, MDA, HMMA, HMA, MDEA, methamphetamine and amphetamine in sweat". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 852 (1–2): 450–458. doi:10.1016/j.jchromb.2007.02.017. PMC 2883875. PMID 17369000.
  3. ↑ Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://www.erowid.org/library/books_online/pihkal/pihkal157.shtml "The amine addition to the methyleugenol world produces 3,4-dimethoxyamphetamine, or 3,4-DMA. The isomer with the other methyl group missing is chavibetol (3-hydroxy-4-methoxyallylbenzene) and is found in the pepper leaf that is used with betel nut."