2,5-Dimethoxy-4-isopropylamphetamine

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

Other namesDOIP; DOiP; DOiPr; 2,5-Dimethoxy-4-isopropylamphetamine; 4-Isopropyl-2,5-dimethoxyamphetamine

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen

Legal status

CA: Schedule I
DE: NpSG (Industrial and scientific use only)
UK: Class A

Quick facts Clinical data, Other names ...

DOiP
Clinical data

Other names	DOIP; DOiP; DOiPr; 2,5-Dimethoxy-4-isopropylamphetamine; 4-Isopropyl-2,5-dimethoxyamphetamine
Routes of administration	Oral^[1]
Drug class	Serotonergic psychedelic; Hallucinogen
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	Unknown^[1]
Identifiers
IUPAC name 1-[2,5-Dimethoxy-(propan-2-yl)phenyl]propan-2-amine
CAS Number	42306-96-7 53581-56-9 (hydrochloride salt)
PubChem CID	44265275
ChemSpider	23108724
UNII	PF0P8RBU0X
CompTox Dashboard (EPA)	DTXSID901032534
Chemical and physical data
Formula	C₁₄H₂₃NO₂
Molar mass	237.343 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C(C(=C1)C(C)C)OC)CC(C)N
InChI 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

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

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

Legal status

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

References

[1]
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]
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.

2,5-Dimethoxy-4-isopropylamphetamine

Use and effects

Interactions

Pharmacology

Pharmacodynamics

Chemistry

Synthesis

Analogues

History

Society and culture

Legal status

See also

References

External links

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