Methylenedioxyamphetamines

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an entactogen with stimulant and minor psychedelic properties.

3,4-Methylenedioxyamphetamine (MDA) is an entactogen, stimulant, and psychedelic drug of the amphetamine and MDxx families that is encountered mainly as a recreational drug. It is usually taken orally.

'3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve') is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.

MBDB, also known as '''N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the nicknames "Eden" and "Methyl-J'''".

group of stereoisomers

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families. It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).

MDAI, also known as 5,6-methylenedioxy-2-aminoindane, is an entactogen of the 2-aminoindane family which is related to MDMA and produces similar subjective effects.

'3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).

Talampanel (INN; development codes GYKI 537773 and LY300164) is a drug which has been investigated for the treatment of epilepsy, malignant gliomas, and amyotrophic lateral sclerosis (ALS).

2-Methyl-3,4-methylenedioxyamphetamine (2-methyl-MDA) is an entactogen-related drug of the amphetamine class. It acts as a selective serotonin releasing agent (SSRA), with IC50 values of 93nM, 12,000nM, and 1,937nM for serotonin, dopamine, and norepinephrine efflux. 2-Methyl-MDA is more potent than MDA and 5-methyl-MDA. However, it is slightly more selective for serotonin over dopamine and norepinephrine release in comparison to 5-methyl-MDA.

MDBU, also known as '3,4-methylenedioxy-N-butylamphetamine or as N-butyl-MDA', is a lesser-known drug. It is the N-butyl derivative of 3,4-methylenedioxyamphetamine (MDA).

5-Methyl-MDA, also known as 5-methyl-3,4-methylenedioxyamphetamine, is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

MDPH, also known as 3,4-methylenedioxyphentermine or as α-methyl-MDA, is a psychoactive drug of the amphetamine family. MDPH was first synthesized by Alexander Shulgin. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.

MDIP, also known as '3,4-methylenedioxy-N-isopropylamphetamine or as N-isopropyl-MDA', is a psychoactive drug of the phenethylamine and amphetamine families. It is the N-isopropyl analogue of 3,4-methylenedioxyamphetamine (MDA).

MDMEOET, also known as '3,4-methylenedioxy-N-methoxyethylamphetamine or as N-methoxyethyl-MDA', is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N-methoxyethyl derivative of MDA.

1,3-Benzodioxolylbutanamine (BDB), also known as 3,4-methylenedioxy-α-ethylphenethylamine or as J, is an entactogen of the phenethylamine, phenylisobutylamine, and MDxx families related to MDMA.

GYKI-52895 is a drug which is a 2,3-benzodiazepine derivative that also shares the 3,4-methylenedioxyamphetamine pharmacophore. Unlike other similar drugs, GYKI 52895 is a selective dopamine reuptake inhibitor (DRI), which appears to have an atypical mode of action compared to other DRIs. Its DRI activity is shared by numerous addictive drugs including amphetamine and its derivatives (e.g. dextromethamphetamine), cocaine, and methylphenidate and its derivatives (e.g. ethylphenidate). However, dopaminergic drugs are also prone to producing emetic effects such as in the case of apomorphine.

6-Methyl-MDA, also known as 6-methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine and MDxx families. It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).

DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA. It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.

'3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM, MDDMA), also known as N,N-dimethyl-MDA or N-methyl-MDMA', is a lesser-known serotonin releasing agent and psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N,N-dimethyl analogue of 3,4-methylenedioxyamphetamine (MDA) and the N-methyl derivative of MDMA. The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.

Methylenedioxyallylamphetamine (MDAL or '3,4-methylenedioxy-N-allylamphetamine') is a lesser-known drug. It is the N-allyl derivative of 3,4-methylenedioxyamphetamine (MDA).

MDMEO, also known as '3,4-methylenedioxy-N-methoxyamphetamine or as N-methoxy-MDA', is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N-methoxy derivative of MDA.

EBDB, also known as '1,3-benzodioxolyl-N-ethylbutanamine, 3,4-methylenedioxy-α,N-diethylphenethylamine, or ethyl-J', is a psychoactive drug of the phenethylamine, phenylisobutylamine, and MDxx families. It is the N-ethyl analogue of BDB (J) and the α-ethyl analogue of MDEA.

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA or DMMDA-1) is a lesser-known psychedelic drug of the amphetamine and MDxx families related to MMDA. It was first synthesized by Alexander Shulgin in the 1960s and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

Methyl-MMDA-2, also known as '2-methoxy-4,5-methylenedioxy-N-methylamphetamine or as 6-methoxy-MDMA', is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N-methylated derivative of MMDA-2, and it is also an analogue of MDMA and 6-methyl-MDA.

MDMP, also known as '3,4-methylenedioxy-N-methylphentermine or as α-methyl-MDMA', is a lesser-known psychoactive drug of the phenethylamine, amphetamine, and MDx families.

MDHOET, also known as '3,4-methylenedioxy-N-hydroxyethylamphetamine or as N-hydroxyethyl-MDA', is a lesser-known drug and a substituted amphetamine. It is also the N-hydroxyethyl analogue of MDA.

MADAM-6, also known as '2,N-dimethyl-4,5-methylenedioxyamphetamine or as 6-methyl-MDMA', is a drug of the phenethylamine, amphetamine, and MDxx families related to MDMA.

MDBZ, also known as '3,4-methylenedioxy-N-benzylamphetamine or as N-benzyl-MDA', is a chemical compound of the phenethylamine, amphetamine, MDxx, and N-benzylphenethylamine families related to MDA. It is the N-benzyl derivative of MDA.

MDPL, also known as '3,4-methylenedioxy-N-propargylamphetamine or as N-propargyl-MDA', is a lesser-known drug and a substituted amphetamine.

MDPR, also known as '3,4-methylenedioxy-N-propylamphetamine or as N-propyl-MDA', is a lesser-known psychoactive drug and a substituted amphetamine.

MDAT, also known as 6,7-methylenedioxy-2-aminotetralin, is a drug of the 2-aminotetralin family developed in the 1990s by a team at Purdue University led by David E. Nichols. It appears to act as a serotonin releasing agent based on rodent drug discrimination assays comparing it to MDMA, in which it fully substitutes for, and additionally lacks any kind of serotonergic neurotoxicity. Hence, MDAT is considered likely to be a non-neurotoxic, putative entactogen in humans.

EBDP, also known as '''N-ethyl-1,3-benzodioxolylpentanamine, 3,4-methylenedioxy-N-ethyl-α-propylphenethylamine, or ethyl-K', is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N''-ethyl analogue of BDP (K).

'3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine, also known as MDMOH, MDHMA, or FLEA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH.

MDMAT, also known as '6,7-methylenedioxy-N-methyl-2-aminotetralin', is a serotonin releasing agent (SRA) and possible entactogen of the 2-aminotetralin family. It is the N-methylated derivative of MDAT, similarly to the relationship of MDMA to MDA. It has been theorized to have less long-term neurotoxicity and less hallucinogenic effects than other MDxx derivatives, but no formal scientific research has been conducted specifically on MDMAT.

MDCPM, also known as '3,4-methylenedioxy-N-cyclopropylmethylamphetamine or as N-cyclopropylmethyl-MDA', is a drug. It is the N-cyclopropylmethyl derivative of MDMA.

6-Bromo-MDA, also known as 6-bromo-3,4-methylenedioxyamphetamine or as 2-bromo-4,5-methylenedioxyamphetamine (2-bromo-4,5-MDA), is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families related to 3,4-methylenedioxyamphetamine (MDA). It is the 6-bromo derivative of MDA. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists 6-bromo-MDA's dose as 350mg orally and its duration as unknown. 6-Bromo-MDA has been reported to produce amphetamine-like effects with no other details provided. However, Daniel Trachsel reported that 6-bromo-MDA was inactive

MBDP, also known as '''N-methyl-1,3-benzodioxolylpentanamine, 3,4-methylenedioxy-α-propyl-N-methylphenethylamine, methyl-K, or UWA-091', is a psychoactive drug of the phenethylamine, phenylisobutylamine, and MDxx families. It is the N''-methyl analogue of BDP (K).