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]}

See also

• 3,4-Ethylidenedioxyamphetamine (EIDA)
• 3,4-Ethylenedioxyamphetamine (EDA)
• 3,4-Ethylenedioxymethamphetamine (EDMA)
• 3,4-Ethylenedioxymethcathinone (EDMC)

References

1. 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.
2. 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.
3. 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.