3,4-Methylenedioxy-N-hydroxyamphetamine

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3,4-Methylenedioxy-N-hydroxyamphetamine
MDOH structure.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(1,3-Benzodioxol-5-yl)-N-hydroxypropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
Formula C10H13NO3
Molar mass 195.218 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NO

3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH, N-hydroxytenamphetamine) 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. [1] In his book PiHKAL (Phenethylamines i Have Known And Loved), Shulgin listed the dosage range as 100–160 mg, and the duration as approximately 3–6 hours. [1] He describes MDOH as being very psychedelic and producing increased pleasure in beauty and nature. [1] He also mentioned several negative side effects also seen with MDMA ("Ecstasy") such as difficulty urinating and internal dryness. [1]

Related Research Articles

<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

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."

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

2C-T-8 is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen.

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

2C-N (2,5-dimethoxy-4-nitrophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin.

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

2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug.

<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">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-ethylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-ethylamphetamine is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL.

<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.

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

2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine 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-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 .

<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">Phenescaline</span> Chemical compound

Phenescaline, or 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a lesser-known psychedelic drug. It is an analog of mescaline. Phenescaline was first synthesized by Alexander Shulgin. In his book PiHKAL , the minimum dosage is listed as 150 mg, and the duration is unknown. Phenescaline produces a threshold effect. Very little data exists about the pharmacological properties, metabolism, and toxicity of phenescaline.

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

2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family.

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">Ariadne (drug)</span> Psychoactive phenethylamine drug

Ariadne is a little-known psychoactive drug. It is a homologue of the psychedelics 2C-D and DOM. Ariadne was first synthesized by Alexander Shulgin. In his 1991 book PiHKAL, Shulgin reported testing Ariadne up to a dose of 32 mg, and reported that it produced "the alert of a psychedelic, with none of the rest of the package". Very little published data exists about the human pharmacology of Ariadne apart from Shulgin's limited testing; unpublished human trials reportedly observed some psychoactive effects, but no hallucinations.

<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.

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

2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book PiHKAL. Shulgin described DOPR as a "heavy duty psychedelic", complete with alterations of the thought process and visual distortion. Very little data exists about the pharmacological properties, metabolism, and toxicity of DOPR.

<span class="mw-page-title-main">2,5-Dimethoxy-4-ethoxyamphetamine</span> Psychedelic drug

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin. In his book PiHKAL, he lists the active dose range as 20–50 mg, and the duration as 10–14 hours. According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.

<span class="mw-page-title-main">Methyl-MMDA-2</span> Chemical compound

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.

<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

  1. 1 2 3 4 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628.