Mescaline (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. It occurs naturally in the peyote cactus, the San Pedro cactus, the Peruvian torch, and other species of cactus. It is also found in small amounts in certain members of the bean family, Fabaceae, including Acacia berlandieri. However those claims concerning Acacia species have been challenged and have been unsupported in any additional analysis.
PiHKAL: A Chemical Love Story is a book by Dr. 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".
Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-examined in the laboratory of David E. Nichols, who prepared a series of mescaline analogues that included escaline, proscaline, and isoproscaline. The effects of this and related mescaline analogues in humans were first described by Alexander Shulgin. In his book PiHKAL , Shulgin lists the dosage range as 40 to 60 mg, consumed orally. The duration of action was stated to be 8–12 hours.
TMAs, also known as trimethoxyamphetamines, are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs of the phenethylamine cactus alkaloid mescaline. The TMAs are substituted amphetamines, however, their action does not resemble that of the unsubstituted compound amphetamine, which is a stimulant and not a psychedelic. It is reported that some TMA's elicit a range of emotions ranging from sadness to empathy and euphoria. TMA was first synthesized by Hey, in 1947. Synthesis data as well as human activity data has been published in the book PiHKAL .
2C-G is a psychedelic phenethylamine of the 2C family. First synthesized by Alexander Shulgin, it is sometimes used as an entheogen. It has structural and pharmacodynamic properties similar to 2C-D and Ganesha. Like many of the phenethylamines in PiHKAL, 2C-G and its homologs have only been taken by Shulgin and a small test group, making it difficult to ensure completeness when describing effects.
Proscaline (4-propoxy-3,5-DMPEA) is a psychedelic and hallucinogenic drug. It has structural properties similar to the drugs mescaline, isoproscaline, and escaline. In PiHKAL, Alexander Shulgin reports that a dose of 30–60 mg produces effects lasting 8–12 hours.
2C-T is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2.
2,4,5-Trimethoxyphenethylamine or is a phenethylamine of the 2C family and was first synthesized by Jansen in 1931. It is a positional isomer of the drug mescaline (3,4,5-trimethoxy).
Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is an analog of mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols. It produces hallucinogenic, psychedelic, and entheogenic effects.
Macromerine is a phenethylamine derivative. It was first identified from the cactus Coryphantha macromeris. It can also be found in C. runyonii, C. elephantidens, and other related members of the family Cactaceae. The plants may have been used by Tarahumara shamans for their entheogenic effects.
4-Desoxymescaline, or 4-methyl-3,5-dimethoxyphenethylamine, is a mescaline analogue related to other psychedelic phenethylamines. It is commonly referred to as DESOXY. DESOXY was discovered by Alexander Shulgin and published in his book PiHKAL.
Cyclopropylmescaline is a lesser-known psychedelic drug. CPM was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 60–80 mg and the duration listed as 12–18 hours. CPM produces closed-eye imagery, visuals, and fantasies. It also causes enhancement of music. Very little data exists about the pharmacological properties, metabolism, and toxicity of CPM.
2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.
Allylescaline (4-allyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is closely related in structure to mescaline. Allylescaline was first synthesized by Otakar Leminger in 1972. The compound was later synthesized by Alexander Shulgin and further described in his book PiHKAL. The dosage range is listed as 20–35 mg, and the duration 8–12 hours. Allylescaline produces an entactogenic warmth, an entheogenic effect, and a feeling of flowing energy. Very little data exists about the pharmacological properties, metabolism, and toxicity of allylescaline.
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.
Propynyl (4-propynyloxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. It is closely related in structure to mescaline. Propynyl was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 80 mg, and the duration listed as 8–12 hours. Propynyl produces a body load and few to no mental effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of propynyl.
3,4-Methylenedioxyphenethylamine, also known as homopiperonylamine, is a substituted phenethylamine formed by adding a methylenedioxy group to phenethylamine. It is structurally similar to MDA, but without the methyl group at the alpha position.
3,4,5-Trimethoxybenzaldehyde is an organic compound. Within this class of compounds the chemical is categorized as a trisubstituted aromatic aldehyde.
2C-T-16 is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL, however while Shulgin began synthesis of this compound he only got as far as the nitrostyrene intermediate, and did not complete the final synthetic step. Synthesis of 2C-T-16 was finally achieved by Daniel Trachsel some years later, and it was subsequently reported as showing similar psychedelic activity to related compounds, with a dose range of 10–25 mg and a duration of 4–6 hours, making it around the same potency as the better-known saturated analogue 2C-T-7, but with a significantly shorter duration of action. Binding studies in vitro showed 2C-T-16 to have a binding affinity of 44nM at 5-HT2A and 15nM at 5-HT2C. 2C-T-16 and related derivatives are potent partial agonists of the 5-HT1A, 5-HT2A, 5-HT2B and 5-HT2C receptors and induce a head-twitch response in mice.
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