Asymbescaline

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Asymbescaline
Asymbescaline.png
Asymbescaline-3d-sticks.png
Names
Preferred IUPAC name
2-(3,4-Diethoxy-5-methoxyphenyl)ethan-1-amine
Other names
3,4-Diethoxy-5-methoxyphenethylamine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3 Yes check.svgY
    Key: VFOAVFQWZYUFQZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C13H21NO3/c1-4-16-12-9-10(6-7-14)8-11(15-3)13(12)17-5-2/h8-9H,4-7,14H2,1-3H3
    Key: VFOAVFQWZYUFQZ-UHFFFAOYAI
  • O(c1c(OC)cc(cc1OCC)CCN)CC
Properties
C13H21NO3
Molar mass 239.315 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Asymbescaline (3,4-diethoxy-5-methoxyphenethylamine) is a lesser-known psychedelic drug. It is a homolog of mescaline. Asymbescaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage range is listed as 200–280 mg, and the duration listed as 10–15 hours. [1] Asymbescaline produces few to no effects. [1] Very little data exists about the pharmacological properties, metabolism, and toxicity of asymbescaline.

See also

Related Research Articles

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">2C-G</span> Chemical compound

2C-G is a psychedelic phenethylamine of the 2C-series. 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.

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

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug and amphetamine. It is an analog of DOM and DOB. It is also closely related to 2C-N.

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

2C-F (4-fluoro-2,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 250 mg. 2C-F may be found as a brownish freebase oil, or as a white crystalline hydrochloride salt.

Ganesha (2,5-dimethoxy-3,4-dimethylamphetamine) is a lesser-known psychedelic drug. It is also a substituted amphetamine. It was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 24–32 mg. The drug is usually taken orally, although other routes such as rectally may also be used. Ganesha is synthesized from 2,5-dimethoxy-3,4-dimethylbenzaldehyde. Ganesha is the amphetamine analog of 2C-G. It is a particularly long lasting drug, with the duration listed in PiHKAL as being 18–24 hours, which might make it undesirable to some users. It is named after the Hindu deity, Ganesha. Very little is known about the dangers or toxicity of ganesha. Effects of ganesha include:

<span class="mw-page-title-main">Aleph (psychedelic)</span> Chemical compound

Aleph is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. It was first synthesized by Alexander Shulgin, who named it after the first letter of the Hebrew alphabet. In his book PiHKAL, Shulgin lists the dosage range as 5–10 mg, with effects typically lasting for 6 to 8 hours.

3,4-Methylenedioxy-<i>N</i>-hydroxyamphetamine Psychedelic amphetamine

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.

<span class="mw-page-title-main">3C-BZ</span> Chemical compound

3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 25–200 mg and the duration as 18–24 hours. According to anecdotal reports from the substance's entry in PiHKAL, 3C-BZ's effects can vary significantly, ranging from intensified emotions and strange dreams, to effects similar to those of LSD or TMA. Very little data exists about the pharmacological properties, metabolism, and toxicity of 3C-BZ.

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">EDMA</span> Chemical compound

3,4-Ethylenedioxy-N-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage is listed as 150–250 mg, and the duration listed as 3–5 hours. According to Shulgin, EDMA produces a bare threshold consisting of paresthesia, nystagmus, and hypnogogic imagery, with few to no other effects. Scientific research has demonstrated that EDMA acts as a non-neurotoxic serotonin releasing agent with moderately diminished potency relative to MDMA, and with negligible effects on dopamine release.

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

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.

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

Symbescaline, or 3,5-diethoxy-4-methoxyphenethylamine, is a lesser-known psychedelic drug. It is an isomer of asymbescaline. Symbescaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage is listed as 240 mg, and the duration listed as unknown. Symbescaline causes few effects, which include alertness and a threshold. Very little data exists about the pharmacological properties, metabolism, and toxicity of symbescaline.

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

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.

<span class="mw-page-title-main">Beatrice (psychedelic)</span> Chemical compound

Beatrice is a lesser-known psychedelic drug. It is a substituted methamphetamine and a homolog of 2,5-dimethoxy-4-methylamphetamine (DOM). Beatrice was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 30 mg, and the duration listed as 6–10 hours. Beatrice produces a vague feeling of openness and receptiveness, and causes a stimulative effect. It also causes diarrhea. Very little data exists about the pharmacological properties, metabolism, and toxicity of beatrice.

<span class="mw-page-title-main">BOD (psychedelic)</span> Chemical compound

BOD (4-methyl-2,5,β-trimethoxyphenethylamine) is a lesser-known psychedelic drug. It is the beta-methoxy analog of 2C-D. BOD was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 15–25 mg, and the duration listed as 8–16 hours. BOD produces strongly distorted open-eye visuals, and some closed-eye visuals. It also has an entheogenic effect and produces humor. Very little data exists about the pharmacological properties, metabolism, and toxicity of BOD.

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.

<span class="mw-page-title-main">F-2 (drug)</span> Psychedelic drug

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.

<span class="mw-page-title-main">F-22 (psychedelic)</span> Chemical compound

F-22 is a lesser-known psychedelic drug of the substituted amphetamine class. F-22 was first synthesized by Alexander Shulgin. In his book PiHKAL, the minimum dosage is listed as 15 mg, and the duration unknown. F-22 produces few to no effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of F-22.

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

Thioproscaline, or 3,5-dimethoxy-4-propylthiophenethylamine, is a lesser-known psychedelic drug. It is the 4-propylthio analog of mescaline. Thioproscaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the dosage range is listed as 20–25 mg, and the duration listed as 10–15 hours. Thioproscaline causes closed-eye visuals, slight open-eye visuals, and a body load. Very little data exists about the pharmacological properties, metabolism, and toxicity of thioproscaline.

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

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.

References