2,5-dimethoxy-4-iodoamphetamine

DOI
Chemical name	1-(2,5-dimethoxy-4-iodophenyl)- propan-2-amine
Chemical formula	C₁₁H₆INO₂
Molecular mass	321.15 g/mol
Melting point	201 °C (hydrochloride)
CAS numbers	64584–34–5, 82830–53–3, 82864–06–0, 99665–04–0
SMILES	N[C@H](C)CC1=C(OC)C=C(I)C(OC)=C1 (R-isomer)

DOI or 2,5-dimethoxy-4-iodoamphetamine is a psychedelic hallucinogenic drug of the phenethylamine family. Despite being a substituted amphetamine it is not a stimulant. DOI has a stereocenter and R-(-)-DOI is the more active stereoisomer. [¹²⁵I]-R-(-)-DOI is used as a radioligand. DOI is active at a dosage of 1.5 – 3.0 mg and has an extremely long duration of 16 – 30 hours.

Pharmacology

The hallucinogenic effect of DOI is mediated by its partial agonistic activity at the 5-HT_2A serotonin receptor, but DOI also has a high binding affinity for the 5-HT_2B and the 5-HT_2C serotonin receptor.

DOI was first synthesized by Alexander Shulgin. The radioactive iodine-125 form of DOI was first developed in the lab of David E. Nichols.

Hallucinogenic phenethylamines edit
{2C-B} {2C-C} {2C-D} {2C-E} {2C-I} {2C-N} {2C-P} {2C-T-2} {2C-T-21} {2C-T-4} {2C-T-7} {2C-T-8} {3C-E} {Br-DFLY} {DOB} {DOI} {DOM} {Escaline} {MDA} {MDBD} {MDEA} {Mescaline} {TMA}

This biochemistry article is a stub. You can help Wikipedia by expanding it.