PiHKAL

'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.

Metaproscaline (MP), also known as 3,4-dimethoxy-5-propoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline. It is the derivative of mescaline in which the methoxy group at the 3 position has been replaced with a propoxy group. In addition, it is a positional isomer of proscaline.

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.

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.

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.

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.

2,5-Dimethoxy-4-amylamphetamine (DOAM), also known as 2,5-dimethoxy-4-pentylamphetamine, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the derivative of DOM in which the methyl group at the 4 position has been replaced with an amyl (pentyl) group. The drug is taken orally.

2C-Se, also known as 4-methylseleno-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It was originally named by Alexander Shulgin as described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Shulgin listed its dose as perhaps 100mg orally and its duration as 6 to 8hours. Its onset was 45minutes, peak effects occurred after 1.5hours, and doses of 50 to 70mg orally produced threshold effects. Shulgin considered 2C-Se to be around three times the potency of mescaline, but was too concerned about toxicity to test it extensively, though he

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. Unlike related drugs like DOB, it produces both pronounced hallucinogenic and amphetamine-like stimulant effects. The drug is taken orally.

psychedelic

drug chemical compound

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.

MEPEA, also known as 3-methoxy-4-ethoxyphenethylamine or as 3-desmethoxyescaline, is a psychoactive drug of the phenethylamine family related to the psychedelic drug mescaline. It is the analogue of escaline in which the methoxy group at the 5 position has been removed.

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.

MDPEA, also known as 3,4-methylenedioxyphenethylamine or as homopiperonylamine, is a possible psychoactive drug of the phenethylamine and methylenedioxyphenethylamine families. It is the 3,4-methylenedioxy derivative of phenethylamine (PEA). The drug is structurally related to 3,4-methylenedioxyamphetamine (MDA), but lacks the methyl group at the α carbon. It is a key parent compound of a large group of compounds known as entactogens such as MDMA ("ecstasy").

Cyclopropylmescaline (CPM), also known as 4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is taken orally and has a very long duration of 12 to 18hours.

α-Ethylmescaline (AEM or 3,4,5-trimethoxy-α-ethylphenethylamine) is a chemical compound of the phenethylamine and phenylisobutylamine families related to the psychedelic drug mescaline. It is the analogue of mescaline and TMA with an ethyl group at the α position of the side chain.

2C-T-13, also known as 4-(2-methoxyethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.

3C-E, also known as 4-ethoxy-3,5-dimethoxyamphetamine or as α-methylescaline (3C-escaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of escaline.

HOT-2, also known as '4-ethylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-2', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-2. The drug is taken orally.

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.

2C-T-8, also known as 4-cyclopropylmethylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.

3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as α-methylbenzscaline (3C-benzscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of benzscaline. The drug was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

2C-F, also known as 4-fluoro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

2,5-Dimethoxy-4-butylamphetamine (DOBU) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to DOM. It is the derivative of DOM in which the methyl group at the 4 position has been replaced with a butyl group. The drug is taken orally.

chemical compound

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

chemical compound

2C-T-17, also known as '4-sec-butylthio-2,5-dimethoxyphenethylamine or as Nimitz', is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

chemical compound

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).

Beta-D, or β-D, also known as 3,4,5-trimethoxy-β,β-dideuterophenethylamine or as β,β-dideuteromescaline, is a psychedelic drug of the scaline family related to mescaline. It is the isotopologue of mescaline in which the two hydrogen atoms at the β position have been replaced with the deuterium isotopes.

Thiobuscaline (TB), or 4-thiobuscaline (4-TB), also known as 3,5-dimethoxy-4-butylthiophenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to the psychedelic drug mescaline. It is the analogue of buscaline in which the butoxy group at the 4 position has been replaced with a butylthio group.

Phenescaline, also known as 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline. It is the derivative of mescaline in which the methoxy group at the 4 position has been replaced with a phenylethoxy group. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists phenescaline's dose as greater than 150mg orally and its duration as unknown. The effects of phenescaline have been reported to include threshold effects and a vague unreal feeling as if one had not had enough sleep. The drug shows

HOT-7, also known as '4-propylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-7', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-7. The drug is taken orally.

Methyl-DMA, also known as '2,5-dimethoxy-N-methylamphetamine or as N-methyl-2,5-DMA', is a psychoactive drug of the phenethylamine, amphetamine, and DOx families. It is the N-methyl derivative of 2,5-dimethoxyamphetamine (2,5-DMA; DOH).

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.

Bis-TOM, or 2,5-TOM, also known as 4-methyl-2,5-dimethylthioamphetamine or as 2,5-dithio-DOM, is a chemical compound of the phenethylamine and amphetamine families related to DOM. It is the analogue of DOM in which the methoxy groups at the 2 and 5 positions have been replaced with methylthio groups.

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).

Meta-DOB, also known as 5-bromo-2,4-dimethoxyamphetamine, is a psychoactive drug of the phenethylamine and amphetamine families related to the psychedelic drug DOB. It is a positional isomer of DOB in which the bromine atom at the 4 position and the methoxy group at the 5 position have been interchanged.

chemical compound

IDNNA, also known as '4-iodo-2,5-dimethoxy-N,N-dimethylamphetamine or as N,N-dimethyl-DOI', is a chemical compound of the phenethylamine, amphetamine, and DOx families. It is the N,N-dimethyl derivative of the psychedelic drug DOI.

chemical compound

Thioproscaline (TP), or 4-thioproscaline (4-TP), also known as 3,5-dimethoxy-4-propylthiophenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the analogue of proscaline in which the propoxy group at the 4 position has been replaced with a propylthio group.

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.

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.

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.

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.

chemical compound

MEM, also known as 2,5-dimethoxy-4-ethoxyamphetamine or as TMA2-4-EtO, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 4 position has been replaced with an ethoxy group. The drug was first described in the scientific literature by Alexander Shulgin by 1968.

Ortho-DOT, also known as 4,5-dimethoxy-2-methylthioamphetamine or as 2-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with a methylthio group. In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).

chemical compound

chemical compound

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).

chemical compound

4-Br-3,5-DMA, also known as 4-bromo-3,5-dimethoxyamphetamine or as 4-bromo-TMA, is a psychoactive drug of the phenethylamine, amphetamine, and 3C families related to mescaline. It is the analogue of TMA in which the methoxy group at the 4 position has been replaced with a bromine atom. In addition, 4-Br-3,5-DMA is a positional isomer of DOB with the methoxy group at the 2 position located instead at the 3 position.

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

Meta-DOT, also known as 5-methylthio-2,4-dimethoxyamphetamine or as 5-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group. In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).

chemical compound

chemical compound