2,5-Dimethoxy-4-isopropylamphetamine

DOiP
Clinical data
Other namesDOIP; DOiP; DOiPr; 2,5-Dimethoxy-4-isopropylamphetamine; 4-Isopropyl-2,5-dimethoxyamphetamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of actionUnknown[1]
Identifiers
  • 1-[2,5-Dimethoxy-(propan-2-yl)phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H23NO2
Molar mass237.343 g·mol−1
3D model (JSmol)
  • COC1=C(C=C(C(=C1)C(C)C)OC)CC(C)N
  • InChI=1S/C14H23NO2/c1-9(2)12-8-13(16-4)11(6-10(3)15)7-14(12)17-5/h7-10H,6,15H2,1-5H3
  • Key:UEEAUFJYLUJWQJ-UHFFFAOYAM

DOiP, or DOiPr, also known as 2,5-dimethoxy-4-isopropylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.[1][2]

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin describes DOiP as being at least an order of magnitude less potent than DOPR, with doses of 20 to 30 mg orally required to produce clear changes in mental state.[1] The specific effects of DOiP have not been described.[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

The receptor interactions of DOiP have been studied.[3][4][2]

DOiP substitutes for DOM in rodent drug discrimination tests, but it is several-fold less potent than other DOx drugs like DOM, DOET, and DOPR, though it is similar in potency to DOBU.[5]

Chemistry

Synthesis

The chemical synthesis of DOiP has been described.[2]

Analogues

Analogues of DOiP include DOM, DOET, DOPR, DOBU, DOiB, and 2C-iP, among others.[2][1]

History

DOiP was first described in the scientific literature by F. Aldous and colleagues in 1974.[6] It was not included as an entry and was only briefly mentioned in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1] However, DOiP was subsequently included as an entry in Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[2]

Society and culture

DOiP is a controlled substance in Canada under phenethylamine blanket-ban language.[7]

See also

References

  1. ^ a b c d e f g Shulgin A, Shulgin A (September 1991). "PiHKAL: A Chemical Love Story #71 DOPR". Transform Press. p. 978. Retrieved 27 June 2015. But this is all with the n-propyl compound. There is a rich collection of misinformation and potential discovery that is associated with the isopropyl isomer. This structural isomer, 2,5-dimethoxyl-4-isopropylamphetamine is properly called DOIP for des-oxy-isopropyl. It has been synthesized and explored in animals and, to a modest extent, in man. The synthesis has proceeded from 2,5-dimethoxyacetophenone by the addition of a methyl group to the carbonyl followed by reduction to the hydrocarbon. Aldehyde formation, nitropropene synthesis with nitroethane, and lithium aluminum hydride reduction are uneventful, providing the hydrochloride salt DOIP, which has a mp of 183–184 °C as an analytical sample. Animal tests (such as rabbit hyperthermia assays), have indicated that the isopropyl compound DOIP is less potent than the propyl prototype, DOPR, by between one and two orders of magnitude. In man, a dose of four milligrams, a rousing dose of DOPR, is without any effects. At 10 milligrams, there is some disturbance but substantially no effects. I have been told that with doses in the 20 to 30 milligram range there are valid changes in mental state, but I have not been told the nature of these changes.
  2. ^ a b c d e Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. ISBN 978-0-9630096-3-0. OCLC 709667010.
  3. ^ Glennon RA, Seggel MR (November 1989). "Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships.". Probing Bioactive Mechanisms. ACS Symposium Series. Vol. 413. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
  4. ^ Seggel MR, Yousif MY, Lyon RA, Titeler M, Roth BL, Suba EA, Glennon RA (March 1990). "A structure-affinity study of the binding of 4-substituted analogues of 1-(2,5-dimethoxyphenyl)-2-aminopropane at 5-HT2 serotonin receptors". Journal of Medicinal Chemistry. 33 (3): 1032–1036. doi:10.1021/jm00165a023. PMID 2308135.
  5. ^ Glennon RA (1989). "Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships" (PDF). NIDA Res Monogr. 94: 43–67. PMID 2575229. Archived from the original (PDF) on May 11, 2023.
  6. ^ Aldous FA, Barrass BC, Brewster K, Buxton DA, Green DM, Pinder RM, et al. (October 1974). "Structure-activity relationships in psychotomimetic phenylalkylamines". Journal of Medicinal Chemistry. 17 (10): 1100–1111. doi:10.1021/jm00256a016. PMID 4418757.
  7. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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