3,4-Isopropylidenedioxyamphetamine

IDA
Clinical data
Other names	IDA; Isopropylidenedioxyamphetamine
Drug class	Monoamine releasing agent; Entactogen; Serotonergic psychedelic; Hallucinogen
Identifiers
	IUPAC name 1-(2,2-dimethyl-1,3-benzodioxol-5-yl)propan-2-amine;
PubChem CID	130544;
ChemSpider	115480;
ChEMBL	ChEMBL3250329;
Chemical and physical data
Formula	C12H17NO2
Molar mass	207.273 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC2=C(C=C1)OC(O2)(C)C)N;
	InChI InChI=1S/C12H17NO2/c1-8(13)6-9-4-5-10-11(7-9)15-12(2,3)14-10/h4-5,7-8H,6,13H2,1-3H3; Key:HJMCSQZYQOFDAL-UHFFFAOYSA-N;

3,4-Isopropylidenedioxyamphetamine (IDA) is a monoamine releasing agent (MRA) of the amphetamine family related to 3,4-methylenedioxyamphetamine (MDA).^[1]^[2]^[3] It is considerably less potent than MDA as an MRA in vitro.^[3]^[1] IDA fully substituted for MDMA and LSD in animal drug discrimination tests, albeit with 5- to 7-fold lower potency than MDA.^[3]^[1]

References

^ ^a ^b ^c Nichols DE, Oberlender R, Burris K, Hoffman AJ, Johnson MP (November 1989). "Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues". Pharmacol Biochem Behav. 34 (3): 571–576. doi:10.1016/0091-3057(89)90560-1. PMID 2623014.
^ Heal DJ, Gosden J, Smith SL (November 2018). "Evaluating the abuse potential of psychedelic drugs as part of the safety pharmacology assessment for medical use in humans". Neuropharmacology. 142: 89–115. doi:10.1016/j.neuropharm.2018.01.049. PMID 29427652.
^ ^a ^b ^c Sáez-Briones P, Hernández A (September 2013). "MDMA (3,4-Methylenedioxymethamphetamine) Analogues as Tools to Characterize MDMA-Like Effects: An Approach to Understand Entactogen Pharmacology". Curr Neuropharmacol. 11 (5): 521–534. doi:10.2174/1570159X11311050007. PMC 3763760. PMID 24403876. Additionally, EDA (ethyl[idene]dioxyamphetamine) has been demonstrated to be nearly equipotent to MDA in its ability to induce [3H]5-HT and [3H]dopamine release from rat hippocampal slices, whereas IDA (isopropylidenedioxyamphetamine) was considerably less potent [114]. In drug discrimination experiments, complete substitution for LSD and MDMA was found for EDA and IDA, which also correlates in the latter case with [125I]DOI displacement.