Isoproscaline

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Isoproscaline
Isoproscaline2DACS.svg
Names
Preferred IUPAC name
2-{3,5-Dimethoxy-4-[(propan-2-yl)oxy]phenyl}ethan-1-amine
Other names
2-(4-Isopropoxy-3,5-dimethoxyphenyl)ethanamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H21NO3/c1-9(2)17-13-11(15-3)7-10(5-6-14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3 Yes check.svgY
    Key: UBNHYNYMUORHAM-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C13H21NO3/c1-9(2)17-13-11(15-3)7-10(5-6-14)8-12(13)16-4/h7-9H,5-6,14H2,1-4H3
    Key: UBNHYNYMUORHAM-UHFFFAOYAL
  • CC(C)Oc1c(cc(cc1OC)CCN)OC
Properties
C13H21NO3
Molar mass 239.31 g/mol
Melting point 163 to 164 °C (325 to 327 °F; 436 to 437 K) (hydrochloride)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.[ citation needed ] It produces hallucinogenic, psychedelic, and entheogenic effects.

Contents

Chemistry

Isoproscaline is in a class of compounds commonly known as phenethylamines, and the full chemical name is 2-(4-isopropoxy-3,5-dimethoxyphenyl)ethanamine.

Effects

Little is known about the psychopharmacological effects of isoproscaline. In his book PiHKAL , Alexander Shulgin lists a psychedelic dosage as being 40–80 mg, with effects lasting 10–16 hours. [1]

Pharmacology

The mechanism that produces the hallucinogenic and entheogenic effects of isoproscaline is most likely to result from action as a 5-HT2A serotonin receptor agonist in the brain, a mechanism of action shared by all of the hallucinogenic tryptamines and phenethylamines.

Dangers

The toxicity of isoproscaline is not known.

Legality

Isoproscaline is unscheduled in the United States; however, because of its close similarity in structure and effects to mescaline, possession and sale of isoproscaline may be subject to prosecution under the Federal Analog Act.

In the UK, its highly likely that this compound would be covered by the "phenylethylamine amendment" to the misuse of drugs act likely rendering it a Class A controlled drug.

See also

Related Research Articles

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<span class="mw-page-title-main">2C-T-21</span> Chemical compound

2C-T-21 is a psychedelic phenethylamine of the 2C family sometimes used as an entheogen. It was first synthesized by Alexander Shulgin.

<span class="mw-page-title-main">2C-T-8</span> Chemical compound

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<span class="mw-page-title-main">Escaline</span> Chemical compound

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.

<span class="mw-page-title-main">2C-T-4</span> Chemical compound

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Trimethoxyamphetamines (TMAs) 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 mechanism of action is more complex than that of the unsubstituted compound amphetamine, probably involving agonist activity on serotonin receptors such as the 5HT2A receptor in addition to the generalised dopamine receptor agonism typical of most amphetamines. This action on serotonergic receptors likely underlie the psychedelic effects of these compounds. It is reported that some TMAs 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.

<span class="mw-page-title-main">Proscaline</span> Chemical compound

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.

<span class="mw-page-title-main">2C-T</span> Chemical compound

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<span class="mw-page-title-main">2C-TFM</span> Chemical compound

2C-TFM is a psychedelic phenethylamine of the 2C family. It was first synthesized in the laboratory of David E. Nichols. It has also been called 2C-CF3, a name derived from the Para-trifluoromethyl group it contains.

<span class="mw-page-title-main">2C-O-4</span> Chemical compound

2C-O-4 (4-isopropoxy-2,5-dimethoxyphenethylamine) is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic, psychedelic, and entheogenic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

<span class="mw-page-title-main">2,5-Dimethoxy-4-nitroamphetamine</span> Chemical compound

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<span class="mw-page-title-main">2C-T-13</span> Chemical compound

2C-T-13 is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL.

<span class="mw-page-title-main">2C-T-15</span> Chemical compound

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<span class="mw-page-title-main">2C-T-17</span> Chemical compound

2C-T-17 or 2,5-dimethoxy-4-(β-secbutylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book PiHKAL .

3,4-Methylenedioxy-<i>N</i>-propylamphetamine Chemical compound

3,4-Methylenedioxy-N-propylamphetamine is a lesser-known psychedelic drug and a substituted amphetamine. MDPR was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 200 mg, and the duration unknown. MDPR is a promoter; by itself it has almost no effects on the mind, but it promotes the effects of hallucinogens, similarly to the closely related MDPH.

<span class="mw-page-title-main">Buscaline</span> Chemical compound

Buscaline (3,5-dimethoxy-4-butoxyphenethylamine) is a chemical compound prepared as a possible psychedelic drug. It is an analog of mescaline. Buscaline was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 150 mg, and the duration is "several hours". Buscaline produces no psychedelic or psychoactive effects, but causes heart arrythmia and light diarrhea. It does not cause any visuals or insights. Very little data exists about the pharmacological properties, metabolism, and toxicity of buscaline.

<span class="mw-page-title-main">Allylescaline</span> Chemical compound

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.

<span class="mw-page-title-main">Thioproscaline</span> Chemical compound

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<span class="mw-page-title-main">Metaproscaline</span> Chemical compound

Metaproscaline, or 3,4-dimethoxy-5-propoxyphenethylamine, is a lesser-known psychedelic drug. It is an analog of proscaline. Metaproscaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage and the duration are unknown. Metaproscaline produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of metaproscaline.

<span class="mw-page-title-main">2C-Se</span> Chemical compound

2C-Se is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL. 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 considered it noteworthy as the only psychedelic drug to contain a selenium atom.

References