PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".
MMDA is a psychedelic and entactogen drug of the amphetamine class. It is an analogue of lophophine, MDA, and MDMA.
DMMDA-2 is a bioactive phenethylamine discussed by Alexander Shulgin in his book PiHKAL ; however, he was not the first to synthesize it. Shulgin comments in his book that a 50 milligram dose of DMMDA-2 produces similar effects to 3,4-methylenedioxy-1-α-methylphenylethylamine. DMMDA-2 can be synthesized from dillapiole.
3,4-Methylenedioxy-N-methoxyamphetamine is a lesser-known psychedelic drug and a substituted amphetamine. It is also the N-methoxy analogue of MDA. MDMEO was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 180 mg. MDMEO may be found as white crystals. It produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDMEO.
MDMEOET, or 3,4-methylenedioxy-N-methoxyethylamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. It is also the N-methoxyethyl analogue of MDA. MDMEOET was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 180 mg. MDMEOET produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDMEOET.
3,4-Methylenedioxy-N-hydroxyamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of MDHMA. MDOH was first synthesized and assayed by Alexander Shulgin. In his book PiHKAL, Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours. He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature. He also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness.
2-Bromo-4,5-methylenedioxyamphetamine (6-Bromo-MDA) is a lesser-known psychedelic drug and a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dose is listed as 350 mg and the duration unknown. It produces stimulant effects but with no psychedelic or empathogenic action. Very little data exists about its pharmacological properties, metabolism, and toxicity.
Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL. Little is known about their dangers or toxicity.
1,3-Benzodioxolylbutanamine is an entactogenic drug of the phenethylamine, amphetamine, and phenylisobutylamine families. It is the α-ethyl analog of MDPEA and MDA and the methylenedioxy analogue of α-ethylphenethylamine.
MDHOET, or 3,4-methylenedioxy-N-hydroxyethylamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. It is also the N-hydroxyethyl analogue of MDA. MDHOET was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 50 mg. MDHOET produces few to no effects. Very little data exists about the pharmacology, pharmacokinetics, effects, and toxicity of MDHOET.
3,4-Methylenedioxy-N-isopropylamphetamine is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as an entactogen, psychedelic, and stimulant. It is the N-isopropyl analogue of 3,4-methylenedioxyamphetamine (MDA). MDIP was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 250 mg. MDIP produces a mild threshold. Very little is known about the pharmacology, pharmacokinetics, effects, and toxicity of MDIP.
F-2, or 6-(2-aminopropyl)-5-methoxy-2-methyl-2,3-dihydrobenzofuran, is a lesser-known psychedelic drug. F-2 was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 15 mg, and the duration unknown. F-2 produces few to no effects at this dose in humans. Animal studies showed it to substitute for the psychedelic drug DOM, but with less than one tenth the potency.
MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA.
N-Methyl-2-methoxy-4,5-methylenedioxyamphetamine is a psychedelic drug of the amphetamine class. It is the N-methylated derivative of MMDA-2, and it is also an analog of MDMA and 6-methyl-MDA.
Methylenedioxyallylamphetamine is a lesser-known psychedelic drug. It is also the N-allyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDAL was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 180 mg, and the duration unknown. MDAL produces few to no effects on its own, but may enhance the effects of LSD. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDAL.
Methylenedioxybutylamphetamine is a lesser-known psychedelic drug. It is also the N-butyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBU was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 40 mg, and the duration unknown. MDBU produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDBU.
Methylenedioxybenzylamphetamine, abbreviated MDBZ, and systematically named 3,4-methylenedioxy-N-benzylamphetamine, is a psychedelic drug. It is the N-benzyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBZ was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 150 mg, and the duration unknown. Very few data exist about the pharmacological properties, metabolism, and toxicity of MDBZ.
MDCPM, or 3,4-methylenedioxy-N-cyclopropylmethylamphetamine, is a lesser-known psychedelic drug. It is the N-cyclopropylmethyl derivative of MDMA. MDCPM was first synthesized by Alexander Shulgin; it is also one of the compounds delineated in a patent by Horrom in 1972. In his book PiHKAL , the minimum dosage is listed as 10 mg, and the duration unknown. MDCPM produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDCPM.
3,4-Methylenedioxy-N,N-dimethylamphetamine is a lesser-known research chemical. It is also the N,N-dimethyl analog of 3,4-methylenedioxyamphetamine (MDA). MDDM was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage is unspecified and the duration unknown. MDDM produces only mild effects that are not well characterized in PiHKAL. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDDM. This compound is however occasionally encountered as an impurity in 3,4-methylenedioxy-N-methylamphetamine (MDMA) which has been synthesized by methylation of MDA using methylating reagents such as methyl iodide. An excess of reagent or a reaction temperature that is too high results in some double methylation of the amine nitrogen, yielding MDDM as well as MDMA. The presence of MDDM as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA.
2,3-Methylenedioxymethamphetamine (2,3-MDMA), also known as ORTHO-MDMA, is a positional isomer of the recreational drug 3,4-MDMA. It is a monoamine transporter (MAT) substrate and inhibitor similarly to 3,4-MDMA. However, while showing similar potency at the norepinephrine transporter (NET), 2,3-MDMA is less potent at the serotonin transporter (SERT). 2,3-MDMA has not been encountered as a recreational or designer drug.
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