DOiPR structure.png
Legal status
Legal status
  • 1-[2,5-Dimethoxy-(propan-2-yl)phenyl]propan-2-amine
CAS Number
PubChem CID
Chemical and physical data
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

2,5-Dimethoxy-4-isopropylamphetamine (also known as DOiP and DOiPr) is a psychedelic drug of the phenethylamine and amphetamine chemical classes.[1][2][3] It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL (Phenethylamines i Have Known And Loved). Shulgin described DOiPR as being at least an order of magnitude weaker than DOPr, with doses of 20–30 mg required to produce valid changes in mental state.[4] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOiPR.

See also


  1. ^ Glennon RA, Seggel MR (November 1989). Interaction of phenylisopropylamines with central 5-HT2 receptors. Analysis by quantitative structure-activity relationships. ACS Symposium Series. Vol. 413. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
  2. ^ 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): 1032–6. doi:10.1021/jm00165a023. PMID 2308135.
  3. ^ 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): 1100–11. doi:10.1021/jm00256a016. PMID 4418757.
  4. ^ Shulgin A, Shulgin A (September 1991). "PiHKAL: A Chemical Love Story #71 DOPR". Transform Press. p. 978. Retrieved 27 June 2015.