3,4-Ethylidenedioxyamphetamine

3,4-Ethylidenedioxyamphetamine
Clinical data
ATC code	none;
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name 1-(2-Methyl-1,3-benzodioxol-5-yl)propan-2-amine;
CAS Number	125299-84-5 ;
PubChem CID	130542;
ChemSpider	115478;
UNII	T927DM865T;
CompTox Dashboard (EPA)	DTXSID401029691 ;
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(N)Cc2ccc1OC(C)Oc1c2;
	InChI InChI=1S/C11H15NO2/c1-7(12)5-9-3-4-10-11(6-9)14-8(2)13-10/h3-4,6-8H,5,12H2,1-2H3; Key:SLXACJFRFCJPAH-UHFFFAOYSA-N;
	(verify)

3,4-Ethylidenedioxyamphetamine (EIDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by David Nichols and coworkers, in the course of research to determine the bulk tolerance around the benzodioxole portion of the MDA molecule. EIDA was found to produce similar effects to MDA in animals but with less than half the potency, while the isopropylidenedioxy derivative (IPIDA, IDA) did not substitute for MDA and instead had sedative and convulsant effects. This shows limited bulk tolerance at this position and (as with 2C-G-5) makes it likely the activity of EIDA will reside primarily in one enantiomer, although only the racemic mix has been studied as yet.^[1]^[2]^[3]

References

^ Nichols DE, Kostuba LJ (October 1979). "Steric effects of substituents on phenethylamine hallucinogens. 3,4-(Methylenedioxy)amphetamine analogues alkylated on the dioxole ring". Journal of Medicinal Chemistry. 22 (10): 1264–7. doi:10.1021/jm00196a022. PMID 513074.
^ Nichols DE, Oberlender R, Burris K, Hoffman AJ, Johnson MP (November 1989). "Studies of dioxole ring substituted 3,4-methylenedioxyamphetamine (MDA) analogues". Pharmacology, Biochemistry, and Behavior. 34 (3): 571–6. doi:10.1016/0091-3057(89)90560-1. PMID 2623014. S2CID 7560526.
^ Trachsel D, Hadorn M, Baumberger F (March 2006). "Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives". Chemistry & Biodiversity. 3 (3): 326–36. CiteSeerX 10.1.1.688.5803. doi:10.1002/cbdv.200690035. PMID 17193269. S2CID 23036634.