2,5-Dimethoxy-4-isopropylamphetamine

DOiP

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

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

See also

• 2C-iP
• 2C-T-4
• DOx

References

1. 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.
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.
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.