3,4-Dimethoxyphenethylamine
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3,4-Dimethoxyphenethylamine
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Names
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Preferred IUPAC name
2-(3,4-Dimethoxyphenyl)ethan-1-amine
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Identifiers
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CAS Number
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3D model (JSmol)
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.003.979
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PubChem CID
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UNII
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CompTox Dashboard (EPA)
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InChI
- InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3 YKey: ANOUKFYBOAKOIR-UHFFFAOYSA-N Y
- InChI=1/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3Key: ANOUKFYBOAKOIR-UHFFFAOYAB
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SMILES
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Properties
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Chemical formula
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C10H15NO2
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Molar mass
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181.23 g/mol
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
Y verify (what is YN ?)
Infobox references
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3,4-Dimethoxyphenethylamine (DMPEA) is a chemical compound of the phenethylamine class. It is an analogue of the major human neurotransmitter 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.
Chemistry
One of the earliest syntheses of DMPEA (then referred to as "homoveratrylamine") was that of Pictet and Finkelstein, who made it in a multi-step sequence starting from vanillin. A similar sequence was subsequently reported by Buck and Perkin, as follows:
3,4-Dimethoxybenzaldehyde (veratraldehyde) →
3,4-Dimethoxycinnamic acid →
3,4-Dimethoxyphenylpropionic acid →
3,4-Dimethoxyphenylpropionamide → 3,4-Dimethoxyphenethylamine
A much shorter synthesis is given by Shulgin and Shulgin:
Derivatives
A known use was in the synthesis of Bevantolol.
Pharmacology
DMPEA has some activity as a monoamine oxidase inhibitor.
Occurrence
DMPEA occurs naturally along with mescaline in various species of cacti such as San Pedro and Peruvian Torch.
See also
References
- ^ A. Pictet and M. Finkelstein (1909). "Synthese des Laudanosins." Ber. 42 1979-1989.
- ^ J. S. Buck and W. H. Perkin (1924). "CCXVIII. Ψ-epiBerberine." J. Chem. Soc., Trans. 125 1675-1686.
- ^ A. Shulgin and A. Shulgin (1991). "PiHKAL A Chemical Love Story", pp. 614-616, Transform Press, Berkeley. ISBN 0-9630096-0-5
- ^ "Erowid Online Books : "PIHKAL" - #60 DMPEA".
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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