MMDA-3b

MMDA-3b, also known as 4-methoxy-2,3-methylenedioxyamphetamine (4-MeO-2,3-MDA), is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to ORTHO-MDA (2,3-MDA).^[2][1] It is the 4-methoxy derivative of ORTHO-MDA and is a positional isomer of MMDA (5-MeO-3,4-MDA) and related compounds like MMDA-2 (6-MeO-3,4-MDA) and MMDA-3a (2-MeO-3,4-MDA).^[1]

Other names4-MeO-2,3-MDA; 4-Methoxy-2,3-methylenedioxyamphetamine; 2,3-Methylenedioxy-4-methoxyamphetamine; 4-Methoxy-ORTHO-MDA; 4-MeO-ORTHO-MDA

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen; Serotonin releasing agent

ATC code

• None

Quick facts Clinical data, Other names ...

MMDA-3b

Clinical data
Other names	4-MeO-2,3-MDA; 4-Methoxy-2,3-methylenedioxyamphetamine; 2,3-Methylenedioxy-4-methoxyamphetamine; 4-Methoxy-ORTHO-MDA; 4-MeO-ORTHO-MDA
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen; Serotonin releasing agent
ATC code	None
Pharmacokinetic data
Onset of action	Unknown[1]
Duration of action	Unknown[1]
Identifiers
IUPAC name 1-(7-methoxy-1,3-benzodioxol-4-yl)propan-2-amine
CAS Number	23693-20-1
PubChem CID	44374894
ChemSpider	23231727
UNII	FM6SU6FD7Y
ChEMBL	ChEMBL159299
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C2C(=C(C=C1)OC)OCO2)N
InChI InChI=1S/C11H15NO3/c1-7(12)5-8-3-4-9(13-2)11-10(8)14-6-15-11/h3-4,7H,5-6,12H2,1-2H3 Key:CLRZDDLQTLKYFH-UHFFFAOYSA-N

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MMDA-3b was included as an entry in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).^[1] He lists its dose as greater than 80 mg orally and its duration as unknown.^[1][3] Shulgin describes 60 mg as being definitely active, qualitatively like 3,4-methylenedioxyamphetamine (MDA), but quantitatively perhaps less, whereas an 80 mg dose of MMDA-3b was said to be no more effective than the 60 mg dose.^[1] He also says that it is similar at these doses to 20 mg MMDA-3a and may be about 3-fold less potent than MMDA-3a.^[1] Elsewhere, MMDA-3b is described as 3-fold more potent than mescaline.^[4]

MMDA-3b has been found to act as an efficacious serotonin releasing agent with little effect on dopamine similarly to MMDA.^[5] For comparison, MDA and MDMA release both serotonin and dopamine, whereas MMDA-2 releases neither serotonin nor dopamine.^[5]

The chemical synthesis of MMDA-3b has been described.^[1] Other 2,3-MDA positional isomers of MMDA-3b include MMDA-4 and MMDA-5.^[2][1]

MMDA-3b was first described in the scientific literature by Shulgin in 1964.^[6] It was subsequently described in greater detail by Shulgin in his book PiHKAL in 1991.^[1] The drug is a controlled substance in Canada under phenethylamine blanket-ban language.^[7]