2,5-Dimethylamphetamine

2,5-Dimethylamphetamine
Clinical data
Other names2,5-DMeA; 2,5-Dimethylphenylisopropylamine; α,2,5-Trimethylphenethylamine
Routes of
administration		Oral
ATC code
  • None
Identifiers
  • SROXXLQATXNIKP-UHFFFAOYSA-N
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H17N
Molar mass163.264 g·mol−1
3D model (JSmol)
  • CC1=CC(=C(C=C1)C)CC(C)N
  • InChI=1S/C11H17N/c1-8-4-5-9(2)11(6-8)7-10(3)12/h4-6,10H,7,12H2,1-3H3
  • Key:SROXXLQATXNIKP-UHFFFAOYSA-N

2,5-Dimethylamphetamine (2,5-DMeA) is a drug of the phenethylamine and amphetamine families which was studied as a potential appetite suppressant in the 1950s but was never marketed. It is the 2,5-dimethyl derivative of amphetamine and is an analogue of 2,5-dimethoxyamphetamine (2,5-DMA) and xylopropamine (3,4-dimethylamphetamine).

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin describes 2,5-DMeA as having little obvious in the way of cardiovascular or central effects at doses of up to 150 mg of the sulfate salt orally. On the other hand, in the The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, he describes the drug as being active at a dose of 50 mg orally and producing appetite suppression without side effects.

Pharmacology

Pharmacodynamics

2,5-DMeA showed sympathomimetic effects with somewhat lower potency than amphetamine in dogs, whereas it was almost inactive in terms of stimulant-like effects in rodents.

Chemistry

The chemical synthesis of 2,5-DMeA has been described. The N-methyl and N,N-dimethyl derivatives of the compound have also been described. Other analogues of 2,5-DMeA include ortetamine (2-methylamphetamine) and 3-methylamphetamine (5-methylamphetamine; PAL-314).

History

2,5-DMeA was first described in the scientific literature by at least 1950.

See also

References

  1. 1 2 3 4 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "An intriguing, but little studied, analogue of 2,5-DMA is the compound with methyls in place of the methoxyls. 2,5-Dimethylamphetamine has been looked at, in man, as a potential anorexic, but there is little effect even at 150 milligrams."
  2. 1 2 3 4 Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.4.5. 2,5-Dimethylphenylisopropylamine A single report has been published concerning the effects of 2,5-dimethylphenylisopropylamine (68) in man (Marsh and Herring, 1950). In studies directed toward the possible anorexogenic effectiveness of homologs of amphetamine, they found that even at levels of 150 mg (of the sulfate, orally), (68) had very little obvious activity on either the cardiovascular system or the central nervous system of man.
  3. 1 2 3 4 5 Marsh DF, Herring DA (November 1950). "The pharmacological activity of the ring methyl substituted phenisopropylamines". The Journal of Pharmacology and Experimental Therapeutics. 100 (3): 298–308. doi:10.1016/S0022-3565(25)04286-7. PMID 14795387.
  4. 1 2 3 Hoffmann-La Roche (1959) Therapeutic compositions containing 1-(2,4-dimethylphenyl)-2-aminopropane. British Patent GB819129. https://patents.google.com/patent/GB819129
  5. 1 2 3 4 5 6 Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
  6. 1 2 3 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.