2,5-Dimethoxy-4-isopropylamphetamine

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

DOiP

Clinical data
Other names	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

See also

• DOx (psychedelics)
• 2C-iP
• 2C-T-4