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".
3,4-Methylenedioxyamphetamine (MDA), sometimes referred to as sass, is an empathogen-entactogen, stimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.
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 street names "Eden" and "Methyl-J".
Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
Methylone, also known as 3,4-methylenedioxy-N-methylcathinone (MDMC), is an entactogen and stimulant drug of the amphetamine, cathinone, and benzodioxole families related to 3,4-methylenedioxymethamphetamine. It is the β-keto or cathinone analogue of MDMA. Methylone is usually taken orally, but is also used by other routes.
2C (2C-x) is a general name for the family of psychedelic phenethylamines containing methoxy groups on the 2 and 5 positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the 4 position, usually resulting in more potent and more metabolically stable and longer acting compounds.
3,4-Methylenedioxyphentermine (MDPH) is a lesser-known 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.
3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine is an entactogen, psychedelic, and stimulant of the phenethylamine and amphetamine chemical classes. It is the N-hydroxy homologue of MDMA ("Ecstasy"), and the N-methyl homologue of MDOH. MDHMA 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 4–8 hours. He describes MDHMA as causing entactogenic and open MDMA-like effects, easing communication, and increasing appreciation of the senses.
2,5-Dimethoxy-3,4-methylenedioxy-1-α-methylphenylethylamine is a lesser-known bioactive derivative compound of the phenethylamine and α-methylphenylethylamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book PiHKAL. Shulgin listed the dosage as 30–75 mg and the duration as 6–8 hours. He reported DMMDA as producing D-lysergic acid diethylamide-like subjective effects: images, mydriasis, ataxia, and time dilation. DMMDA is not mentioned much in literature outside PiHKAL unlike 2,5-dimethoxy-4-bromo-1-phenylethylamine.
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.
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.
Substituted phenethylamines are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by replacing, or substituting, one or more hydrogen atoms in the phenethylamine core structure with substituents. Phenylethylamines are also generally found to be central nervous system stimulants with many also being entactogens/empathogens, and hallucinogens.
Substituted amphetamines, or simply amphetamines, are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).
MDMAT (6,7-methylenedioxy-N-methyl-2-aminotetralin) is a selective serotonin releasing agent (SSRA) and entactogen drug. 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.
6-MAPDB is a chemical compound which might be an entactogenic drug. It is structurally related to drugs like 6-APDB and 6-MAPB, which have similar effects to MDMA and have been used as recreational drugs. 6-MAPDB has never been studied to determine its pharmacological activity, though it is the N-methyl derivative of 6-APDB which is known to be a selective serotonin releaser.
Substituted piperazines are a class of chemical compounds based on a piperazine core. Some are used as recreational drugs and some are used in scientific research.
3,4-Ethylenedioxyamphetamine (EDA), also known as EDA-6, is a drug of the amphetamine family related to 3,4-methylenedioxyamphetamine (MDA). It is closely related to analogues including 3,4-ethylenedioxymethamphetamine (EDMA), 3,4-ethylidenedioxyamphetamine (EIDA), and 3,4-isopropylidenedioxyamphetamine (IDA). EDMA, the N-methylated analogue of EDA, is known to be a serotonin–norepinephrine–dopamine releasing agent (SNDRA). According to Alexander Shulgin however, the drug produced limited psychoactive effects in humans at doses in the range of 150 to 250 mg. Threshold effects with EDA in humans have been reported to have occurred at a dose of 150 mg in humans.
1,3-Benzodioxolylpentanamine (BDP), also known as K or as 3,4-methylenedioxy-α-propylphenethylamine (MDPPEA), is a drug of the phenethylamine and amphetamine families. It is the parent compound of 1,3-benzodioxolyl-N-methylpentanamine and 1,3-benzodioxolyl-N-ethylpentanamine, as well as of pentylone (βk-MBDP). The drug was synthesized by Alexander Shulgin and described in PiHKAL. In contrast to MBDP and EBDP however, it is not known to have ever been tried by humans. Very little is known about BDP.
1-(3,4-Methylenedioxyphenyl)-2-propylaminopentane (MPAP), also known as 3,4-methylenedioxy-α,N-dipropylphenethylamine, N-propyl-1,3-benzodioxolylpentanamine (PDBP), or propyl-K, is a monoaminergic activity enhancer (MAE) of the phenethylamine, amphetamine, and α-propylphenethylamine families that is closely related to phenylpropylaminopentane (PPAP). It is an analogue of PPAP and benzofuranylpropylaminopentane (BPAP) with a benzodioxole ring instead of a phenyl or benzofuran ring, respectively.
Mydecine Innovations Group, or simply Mydecine, is an American and Canadian pharmaceutical company that is developing psychedelics and entactogens as medicines.
