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2,6-Dimethoxyphenethylamine

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2,6-Dimethoxyphenethylamine
Clinical data
Other names2,6-DMPEA; DMPEA-5
ATC code
  • None
Identifiers
  • 2-(2,6-dimethoxyphenyl)ethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC10H15NO2
Molar mass181.235 g·mol−1
3D model (JSmol)
  • COC1=C(C(=CC=C1)OC)CCN
  • InChI=1S/C10H15NO2/c1-12-9-4-3-5-10(13-2)8(9)6-7-11/h3-5H,6-7,11H2,1-2H3
  • Key:VIHNHLSXVPNVPY-UHFFFAOYSA-N

2,6-Dimethoxyphenethylamine (2,6-DMPEA), also known as DMPEA-5, is a drug of the phenethylamine family related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).[1][2] It is one of the positional isomers of dimethoxyphenethylamine.[1][2]

Its in-vitro metabolism and effects on cat behavior have been described.[1][3][4][5] The drug showed no activity as a norepinephrine reuptake inhibitor or releasing agent in vitro.[1][6] It is relatively unaffected by monoamine oxidase (MAO) and is said to be behaviorally inactive in animals.[2] The effects of 2,6-DMPEA in humans have not been reported and are unknown.[1]

2,6-DMPEA was first described in the scientific literature by at least 1962.[1][2][7] It was included as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1]

Notable derivatives of 2,6-DMPEA include the psychedelic and related drugs Ψ-2C-T-4 (psi-2C-T-4), ψ-DOM (psi-DOM), and CT-5172.[8][9][2]

See also

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References

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  1. ^ a b c d e f g Shulgin A, Manning T, Daley PF (2011). "#48. 2,6-DMPEA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 84–85. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ a b c d e Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  3. ^ Clark LC, Benington F, Morin RD (October 1964). "The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines". The Alabama Journal of Medical Sciences. 1: 417–429. PMID 14230671.
  4. ^ Clark LC, Benington F, Morin RD (May 1965). "The effects of ring-methoxyl groups on biological deamination of phenethylamines". Journal of Medicinal Chemistry. 8 (3): 353–355. doi:10.1021/jm00327a016. PMID 14323146.
  5. ^ Ernst AM (May 1965). "Relation between the structure of certain methoxyphenylethylaminederivatives and the occurrence of a hypokinetic rigid syndrome". Psychopharmacologia. 7 (6): 383–390. doi:10.1007/BF00402360. PMID 5890661.
  6. ^ Rotman A, Lundstrom J, McNeal E, Daly J, Creveling CR (February 1975). "Norepinephrine uptake sites in cardiac tissue. Lack of affinity of 6-hydroxynorepinephrine and related compounds". Journal of Medicinal Chemistry. 18 (2): 138–142. doi:10.1021/jm00236a005. PMID 1120979.
  7. ^ Marley E (July 1962). "Action of some sympathomimetic amines on the cat's iris, in situ or isolated". The Journal of Physiology. 162 (2): 193–211. doi:10.1113/jphysiol.1962.sp006926. PMC 1359651. PMID 14470081.
  8. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4.
  9. ^ 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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