3,4-Dimethoxyphenethylamine

3,4-Dimethoxyphenethylamine
IUPAC name

2-(3,4-dimethoxyphenyl)ethylamine
Identifiers
CAS number 120-20-7 Y
PubChem 8421
ChemSpider 8114 Y
ChEBI CHEBI:136995 Y
ChEMBL CHEMBL26019 Y
Jmol-3D images Image 1
Properties
Molecular formula C10H13NO2
Molar mass 181.23 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline which is 3,4,5-trimethoxyphenethylamine.

DMPEA was first synthesized and assayed by Alexander Shulgin.[1] In his book PiHKAL, he describes DMPEA as producing no effects when tested even with very high doses, such as 1,000 mg orally or 10 mg via intravenous injection.[1] As a result, it can be assumed that it is biologically inactive.[1] However, it has been shown to have some activity as a monoamine oxidase inhibitor.[2]

DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.[3][4][5]

See also

References

  1. ^ a b c "Erowid Online Books : "PIHKAL" - #60 DMPEA". http://www.erowid.org/library/books_online/pihkal/pihkal060.shtml. 
  2. ^ Keller WJ, Ferguson GG (July 1977). "Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase". Journal of Pharmaceutical Sciences 66 (7): 1048–50. doi:10.1002/jps.2600660741. PMID 886445. 
  3. ^ Lundström J (December 1970). "Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R". Acta Pharmaceutica Suecica 7 (6): 651–66. PMID 5511715. 
  4. ^ Pummangura S, Nichols DE, McLaughlin JL (October 1977). "Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii". Journal of Pharmaceutical Sciences 66 (10): 1485–7. doi:10.1002/jps.2600661037. PMID 925910. 
  5. ^ Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG (1977). "Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus". Lloydia 40 (6): 585–90. PMID 600028. 

External links

Phenethylamines
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(and relatives..)
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Miscellaneous
Drugs from PiHKAL

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